DOE v. PORTLAND PUBLIC SCHOOLS

UNITED STATES DISTRICT COURT

DISTRICT OF MAINE

MS. DOE, on behalf of her minor )

son, JOHN DOE )

)

Plaintiff, )

v. )

) No. 2:23-cv-00409-JAW

PORTLAND PUBLIC SCHOOLS, )

et al, )

)

Defendants. )

ORDER ON MOTION FOR A TEMPORARY RESTRAINING ORDER

A mother, on behalf of her minor son, moves the Court for a temporary

restraining order to maintain the son’s placement at his current high school, alleging

the school district, by mandating his transfer to another local high school, is

discriminating against the son because of his disability and violating his First

Amendment right to free speech. In addition, the mother requests that the Court

urgently consider her demand that the Court enjoin the Defendants and require them

to include her son’s name on the roster of school athletes competing in the New

England Cross Country meet.

The Court concludes the mother is unlikely to succeed on the merits on her

First Amendment claim because although the son’s speech occurred off campus, his

First Amendment rights must give way to the school district’s need to prevent further

disruption of learning-related activities and to protect others in the school

community—particularly teenage females on campus. The Court also concludes that

the mother is unlikely to succeed on either of her disability discrimination claims

because the record does not indicate the son’s disability diagnoses were the but-for or

animating cause of the school district’s decision to transfer the son to another local

high school. The Court further concludes that the mother has failed to carry her

burden of demonstrating that the son will suffer irreparable harm absent a

temporary restraining order because the record suggests the son will be able to

graduate on time, and an inability to participate in interscholastic athletics and the

attendant loss of college recruiting opportunities does not constitute irreparable

harm. Lastly, the Court concludes that both the balance of the equities and the public

interest weight in favor of the school district as their decision helps ensure the safety

and well-being of numerous community members, including the son. The Court,

therefore, holds that the mother failed to meet the high burden required for the

extraordinary remedy of a temporary restraining order and accordingly denies the

motion seeking it.

I. PROCEDURAL BACKGROUND

On October 30, 2023, Ms. Doe, on behalf of her minor son, John Doe, filed a

complaint against Portland Public Schools (PPS), as well as PPS’ superintendent Dr.

Ryan Scallon and deputy superintendent Aaron Townsend. Compl. (ECF No. 1). Ms.

Doe’s complaint brought forth 1) a claim pursuant to 42 U.S.C. § 1983, that PPS

violated John Doe’s First Amendment rights, 2) a claim pursuant to 29 U.S.C. § 749,

that PPS engaged in intentional discrimination against John Doe due to his disability

in violation of section 504 of the Rehabilitation Act of 1973, and 3) a claim pursuant

to 42 U.S.C. § 12132, that PPS intentionally discriminated against John due to his

disability in violation of Title II of the American with Disabilities Act. Id.

Also on October 30, 2023, Ms. Doe filed a Motion for Temporary Restraining

Order and Preliminary Injunction, Mot. for Temp. Restraining Order and Prelim. Inj.

(ECF No. 4) (Pl.’s Mot.),1 requesting that the Court require PPS “to maintain the

status quo by permitting John to return immediately to his academic and athletic

activities at [Portland High School], notwithstanding [PPS’] unlawful involuntary

transfer order.” Id. at 20.

The following day, October 31, 2023, following attorney appearances for PPS,

the Court held a hearing on the pending motion for temporary restraining order

(TRO) wherein counsel agreed to an expedited briefing schedule. Hearing (ECF No.

9).2 On November 1, 2023, PPS responded in opposition. Defs.’ Opp. to Emergency

Mot. for a Temp. Restraining Order (ECF No. 12) (Defs.’ Opp’n). On November 2,

1 As the Court explained during the October 31, 2023 telephone conference of counsel, Federal

Rule of Civil Procedure 65(b) addresses motions for TROs as if they have been filed on an ex parte

basis. FED. R. CIV. P. 65(b)(1) (“The court may issue a temporary restraining order without written or

oral notice to the adverse party or its attorney if . . . .”). Here, as counsel for the Defendants has

received notice and entered their appearance, this procedure is something of a hybrid between a motion

for TRO and for preliminary injunction. Nevertheless, as the Plaintiff expressly requested the Court

to act quickly on the requested relief, the Court is treating this motion as a request for a TRO and will

address the next steps, including disposition of the motion for preliminary injunction, with counsel at

the telephone conference scheduled for Monday, November 6, 2023.

2 During the October 31, 2023 telephonic conference of counsel, counsel for the Plaintiff

requested a temporary restraining order to allow John Doe to participate in the Maine State Cross-

Country meet, which is scheduled for November 4, 2023. Following the conference of counsel, and

upon learning that the deadline for including John on the list of runners from Portland High School

had already passed, the Plaintiff decided to instead seek a temporary restraining order to allow John

to participate in the New England Championships, which are scheduled for November 11, 2023. The

Court thus adjudicates this TRO in a timely fashion so that the parties will know the Court’s ruling

before the registration deadline for the New England Championships.

2023, Ms. Doe replied. Reply to Mot. re Mot. for Temporary Restraining Order and

Preliminary Injunction (ECF No. 13) (Pl.’s Reply).

II. FACTUAL BACKGROUND

John Doe is a seventeen-year-old twelfth-grade student at Portland High

School (PHS), where he is a member of the National Honor Society and maintains a

GPA of 97. Pl.’s Mot. at 2. John has been enrolled at PHS throughout high school

and competes on multiple varsity teams. Id. He has earned the position of senior

captain on the boy’s cross-country team and run as part of the PHS track team at the

New England Championships several times in multiple events. Id. He has competed

twice at the National Championships for the 4x800 relay team. Id. “Given his

academic and athletic strengths, John is currently being recruited by several colleges

and universities.” Id. at 3. “John also participates in the carpentry program at the

Portland Arts and Technology High School (PATHS) for half of each school day,”

having earned a gold medal in carpentry at the 2023 Maine Skills USA Leadership

and Skills Competition. Id.

John, however, has been unable to continue his schooling and athletic career

at PHS and his carpentry program at PATHS due to some of his behavior. In early

February 2023, one of John’s friends provided a PHS social worker with a screen shot

of a text message in which John had written, among other things, “Watch bro. I will

become the greatest to ever, or if all goes wrong you’ll see me on the news for mass

murder and rape. It seems like I’m joking, but trust me I’m not. Watch.” Defs.’ Opp’n

at 2. Later that month and into March and April, a friend of John’s shared text

messages authored by John and conveying John’s obsession with one of his female

classmates, stating “I have been obsessed with her for months,” “I can’t stop looking

at her location,” “I could put [female Student 1] out there on my snapchat story when

I rape her.” Id. On May 11 2023, “John posted a picture from prom on Instagram

showing him getting into a car with his face photoshopped with half a face of an angel

and half a face of a devil and blood spattered on his car.” Id., Attach.1, Decl. of Aaron

Townsend ¶ 15 (Townsend Decl.). On May 19, 2023, John sent two music videos to a

female classmate, “one about a boy killing his girlfriend and one about killing cats.”

Id. “PHS staff attempted to address each of the incidents by communicating with Ms.

Doe, providing support to John, and trying to connect John with counselling.” Defs.’

Opp’n at 2; see also Townsend Decl. ¶ 16.

Since August 2, 2023 “John has been in regular treatment with the Maine

Medical Center Outpatient Child/Adolescent Psychiatry unit” and “has been

diagnosed with Prolonged Grief Disorder and Major Depressive Disorder, Recurrent,

Mild.” Pl.’s Mot., Attach.2, Declaration of Robyn L. Ostrander, M.D. in Support of

Pl.’s Mot. for Temp. Restraining Order and Prelim. Inj. ¶ 4 (Ostrander Decl.).

In late August 2023, John sent to a peer a “lengthy sexualized text message”

which he had composed and sent to another peer in June 2023. Pl.’s Mot. at 4. “The

text referenced (but was not sent to) a female peer and described her as the object of

his sexual desire.” Id. In one passage it stated: “With the increased risk of murder

when around me, she is scared. I have shown her what I an[sic] capable of. I have

given her ideas of what my free mind wants to do to her. With the sign of a pocket

knife the last time I saw her, she is completely speechless.” Defs.’ Opp’n at 3. Ms. Doe

avers “John mistakenly had a utility knife from his PATHS carpentry program in his

bag at one of the spring track practices.” Pl.’s Reply at 2. Regardless, the friend

provided administrators at PHS with a copy of the message on September 22, 2023.

Defs.’ Opp’n at 2-3. This message was also “displayed on a phone and passed around

a class by students so that it was viewed by every student in the room” and later

“shared between students during the school day”. Id., Attach.11, Decl. of Sarah Obare

¶¶ 4-5 (Obare Decl.).

Given the contents of the message, the PHS administration decided to suspend

John “in compliance with [the PPS Board Policy on Suspension of Students],”

“because they believed that doing so was necessary for the safety, health, and

wellbeing of John and the school community, and to give them time to accurately

assess the risk that John posed to the school.” Defs.’ Opp’n at 3 (internal citations

omitted).

“[I]mmediately after John was suspended on September 22”, he sent a voice

memo to another student. Pl.’s Reply at 1-2. In the four-minute voice memo, John

“indicated he knew he was not to be contacting her and stated that he should kill

himself.” Defs.’ Opp’n at 5. That same day, John showed up for the bus to go to the

school’s cross-country meet and had to be told by the coach that he could not attend.

Defs.’ Opp’n, Attach. 11 ¶ 13.3

3 Ms. Doe and PPS contest whether it was made clear to the Does that John was also suspended

from co-curricular activities including cross-country. Obare Decl. ¶ 13; Pl.’s Reply, Attach. 1, Reply

Decl. of Ms. Doe in Support of Pl.’s Mot. for Temp. Restraining Order and Prelim. Inj. ¶ 5(g) (Reply Doe

Decl.).

Several students then spoke to Assistant Principal Obare about their concerns

about John and others spoke with other administrators. Obare Decl. ¶ 6. Other

students have expressed concern about John harming himself, harming others, and

failing to respect boundaries with female students as exemplified by him repeatedly

saying things like “I know where you live” or “I can find where you live” as well as

repeatedly calling and contacting them, at times discussing sexual material. Id. ¶¶

7-10. “A total of five female students have requested that the school prohibit John

from having contact with them.” Id. ¶ 11.

“The first step for the school was to perform a Comprehensive School Threat

Assessment Guidelines (‘CSTAG’) threat assessment.” Defs.’ Opp’n at 3. “A Portland

social worker conducted the assessment” and “both Ms. Doe and John participated.”

Pl.’s Mot. at 5. During the interviews, PHS administrators learned of other

“troubling” communications, including “messages sent by John wanting students to

be hurt,” “a message saying that [another student] needed to ‘be humbled,’” a message

to another male student “referencing a group of girls that stated ‘You’re a big strong

dude. Imagine what you could do to those girls over there.’” Defs.’ Opp’n at 3-4

(internal citations omitted). The administration “also learned that the PHS cross-

country coach did not want John on his team due to John’s sexually harassing

behavior and threats toward female team members.” Id. at 4.

Although “PHS’s principal informed the Does that upon completion of the

assessment and review by the administrators on September 27, John would be able

to return to PHS the following day,” the “principal called Ms. Doe on September 28

to request a meeting with her and Portland’s social worker. At the meeting, the

principal requested more time to develop the steps for John’s re-entry to PHS.” Pl.’s

Mot. at 5. More time was needed because under the CSTAG criteria, “evaluators

determined that John posed a ‘very serious substantive risk,’ the highest category of

threat under the CSTAG criteria,” Defs.’ Opp’n at 4, and “PPS felt as though it could

not rule out whether John posed a significant risk to the PHS community and

himself,” id. Ms. Doe “never received the results of the CSTAG.” Pl.’s Reply at 2.

Nonetheless, the parties then “agreed to meet again on October 4 to go over the points

of a proposed re-entry plan so John could get back to PHS.” Id.

“At the meeting on October 4, Defendant Townsend, the Deputy

Superintendent, joined the principal” and “requested a second assessment of John by

a psychologist before permitting him to return to PHS,” Pl.’s Mot. at 5, which Ms. Doe

agreed to, Defs.’ Opp’n at 4. PPS required John to remain “out of school for several

days,” Pl.’s Mot. at 5, until “Dr. Moran completed the risk assessment on October 19,

2023,” Defs.’ Opp’n at 4. “Meanwhile, John participated in private therapy and

completed his PHS school work through tutorials.” Pl.’s Mot. at 5.

John was barred, however, from his carpentry classes at PATHS and from

participating in athletics. As a result, he was unable to participate in the Cross-

Country Regional Championships on October 21, 2023.” Pl.’s Mot. at 5. PPS also

omitted John from the state championship roster submitted in mid-October while

John was undergoing the risk assessment, rendering it impossible that he run at the

November 4, 2023 meet. Pl.’s Reply at 3.

Aware of John’s June 2023 text message which he resent in August 2023, as

well as his other texts and the blood-splatter and devil face collage created by John

in Spring 2023, and having discussed the June 2023 message with John, his private

psychiatrist, Dr. Robyn L. Ostrander believes John was feeling lonely and unseen and

needed to be recognized. Ostrander Decl. ¶ 9. She further believes it is “important

for the continuation of John’s therapeutic progress that [his] relationships and

activities be restored to his life as soon as possible. Id. ¶ 11. Ultimately, Dr.

Ostrander “encouraged Portland to permit him to continue his education at PHS and

get back to his friends and athletics.” Pl.’s Mot. at 6.

During his assessment with Dr. Moran, the psychologist designated by PPS to

perform John’s risk assessment, John “acknowledged that he was having occasional

thoughts of raping a girl and of killing her. However, he said that he had no plans to

act on these thoughts.” Defs.’ Opp’n, Attach. 7, Psychological Evaluation at 3. John

went on to say that “he currently has occasional negative sexual thoughts, but no

plan to act on them” and then again said “I still have intrusive thoughts of raping

someone sometimes, but no plans.” Id. One of Dr. Moran’s tests suggests that John

“responded to items in a highly guarded and defensive fashion.” Id. In his

assessment, Dr. Moran ultimately deferred to the judgment of PHS staff but made

recommendations that John continue to engage in community-based therapy, meet

weekly with the PHS social worker, understand expectations prior to returning to

school, prepare for negative comments that may be made by peers, learn to control

his negative thoughts, learn healthy coping skills, and develop a positive self-image.

Defs.’ Opp’n at 4; Pl.’s Mot. at 6-7. John has “agreed to abide by all of the

recommendations set forth in the psychological assessment report.” Pl.’s Mot. at 7.

While this counseling and assessment was underway, proceedings were

simultaneously underway before the state of Maine District Court, after the mother

of the female peer named in John’s text filed a complaint seeking protection from

harassment by John. Sealed Additional Attachs., Attach. 3, (Order for Protection

from Harassment). On October 20, 2023, the proceedings ended with issuance of a

stipulated order seen and agreed to by both parties. Id. “Under the terms of the

court’s stipulated order, John was cleared to return to school and athletics at PHS

with conditions, including refraining from physical and electronic contact with the

female peer and not attending team dinners that involve both the boys’ and girls’

teams.” Pl.’s Mot. at 7-8.

The day after Dr. Moran completed his assessment and the same day the Court

issued its stipulated order, October 20, 2023, PHS administration received

information that John had sent a girl on the cross-country team the four-minute voice

memo described above talking about killing himself and that John shared TikTok

videos depicting a female student in a bikini with a friend via text, which then

circulated around the PHS cross-country team. Defs.’ Opp’n at 5; Pl.’s Reply, Attach.

1, Reply Decl. of Ms. Doe in Support of Pl.’s Mot. for Temp. Restraining Order and

Prelim. Inj. ¶¶ 5(b)-(c) (Reply Doe Decl.). This TikTok video was created on September

9, 2023. Id.

At that point, “PPS determined that it was in the best interests of John and

the entire PHS community that John return to a different high school in the District.”

Defs.’ Opp’n at 5. PPS does not mean for the transfer to be disciplinary, will not

record the transfer in John’s student record as discipline, and instead believes it is

“intended to facilitate John’s re-entry into school and give him a fresh start at a

different school” as “it is not in John’s best interest to return to PHS this year because

information and misinformation about John is so widespread.” Id.; see also Defs.’

Townsend Decl. ¶ 35. “The PHS administration likewise believes that the plan serves

the best interests of students at PHS, many of whom have exhibited real fear and

anxiety because of what John has written.” Defs.’ Opp’n at 5. “PHS administration

also considered its ability to meet its obligation to protect students—in the

circumstances here, female students—from sexually harassing conduct in light of

John’s continued contact with females at PHS even after expressing an

understanding that he should not engage in such contact.” Id.

Given all of this, “PPS worked with Casco Bay [High School] to put together a

schedule and re-entry plan for John; and provided with the option for John to attend

Deering High School as well.” Id. “PPS is confident that John will receive comparable

instruction at any of the Portland high schools, and, although John’s cross-country

coach at PHS indicated that John should not be on the PHS team, John’s re-entry

plan will enable him to join the running team at Deering High School.” Id. at 5-6.

PPS issued this re-entry, or return to school, plan on October 25, 2023. Pl.'s Mot.,

Attach. 1, Decl. of Ms. Doe in Support of Pl.’s Mot. for Temp. Restraining Order and

Prelim. Inj. ¶ 30 (Doe Decl.).

Ms. Doe believes this “amounts to an involuntary transfer” as it prohibits John

from taking classes or competing in athletics for PHS. Pl.’s Mot. at 8. While John

will not be able to run on November 4, 2023, Ms. Doe remains hopeful he will be able

to run at the New England championship meet to be held on Saturday, November 11,

2023. Reply Doe Decl. ¶ 3. To do so, however, PPS would need to add John to the

roster for this event by this Sunday, November 5, 2023. Id. If successful at the New

England championship meet, the PHS cross-country team would be invited to the

Nationals cross-country meet, a goal of John’s. Id. ¶ 4. Ms. Doe, therefore, requests

a temporary restraining order to compel PPS to allow John to restart his athletic

eligibility and academic programming at PHS and PATHS.

III. THE PARTIES’ POSITIONS

A. Ms. Doe’s Motion for TRO

Ms. Doe seeks a TRO pursuant to Federal Rule of Civil Procedure 65 to “stop

[PPS]] plan to transfer her son, John Doe, involuntarily to a different high school,”

Pl.’s Mot. at 1, and to require PPS to permit “John to return immediately to his

academic and athletic activities at [Portland High School], notwithstanding

Portland’s unlawful involuntary transfer order.” Id. at 20. Ms. Doe contends the

order is unlawful because it “violates John’s First Amendment right to free speech

and amounts to discrimination on the basis of disability.” Id. at 1. Ms. Doe notes she

bears the burden of establishing that each of the four factors for preliminary

injunctive relief weighs in her favor, id. at 10, and she asserts they all do. Id. at 11-

19.

Beginning with the likelihood of success on the merits on the First Amendment

right to free speech claim, Ms. Doe argues PPS’ “alleged basis for John’s involuntary

transfer consists only of off-campus speech in the form of private text messages to

peers that later were forwarded to the school.” Id. at 11. John’s speech happening

off-campus, Ms. Doe contends, limits the school’s interest in regulating it. Id. at 11-

12. Ms. Doe also contends that John’s text “does not contain a ‘true threat’ as defined

by the Supreme Court” because “John’s speech did not rise to the required level of

severity or even convey an intent to harm.” Id. at 12. Pointing to the “most

concerning portion of text,” Ms. Doe asserts it “does not state a direct threat to commit

harm, much less a serious expression of an intent to commit an act of violence.” Id.

at 12-13.

“Even if the statement could be classified as a true threat,” Ms. Doe argues,

PPS’ “involuntary transfer would still violate the First Amendment” because “the

government may not sanction a true threat without a showing of mens rea.” Id. at

13. Believing there to be no evidence “that John consciously accepted a substantial

risk of inflicting serious harm on the female peer through his text message,” Ms. Doe

contends John is protected by the First Amendment from being sanctioned for his

speech. Id. at 14.

Ms. Doe then argues that the “involuntary transfer violates John’s right to be

free from discrimination based on his disability” as protected by both the ADA and

Section 504 of the Rehabilitation Act. Id. Ms. Doe contends “there is no evidence

that John presents a risk of harm to other PHS students or PHS staff,” that his

“treating physician has stated as much and urged [PPS] to get him back to his school

routine and back with his peer supports on the cross-country and track teams at

PHS.” Id. at 15. Ms. Doe concludes by saying that “John continues to be in treatment

and poses no risk of harm, so such stereotypical fears of a student regarded as having

a mental health disability cannot serve as a legitimate basis for Portland’s actions.”

Id. at 16.

Regarding the second factor, likelihood of irreparable harm, Ms. Doe argues

that absent prompt injunctive relief, John will be deprived of educational

opportunities, “involuntarily forced to sever his relationships with PHS,” have “his

college recruitment efforts . . . be needlessly interrupted and damaged, as he

undoubtedly will have to explain why he no longer attends or competes for PHS,” and

endure “further irreparable injury in the form of adverse effects on his mental

health.” Id. at 16-18.

With respect to the third factor, the balance of equities, Ms. Doe argues “the

harm to [John] in the absence of injunctive relief would be severe” while “[l]ittle if

any harm” “would befall [PPS] were John to return to PHS, just as Portland

administrators had routinely promised John and his mother.” Id. at 18.

Concerning the fourth factor, whether the injunction serves the public interest,

Ms. Doe contends “the public interest weighs in favor of requiring [PPS] to (a) (a)

honor John’s First Amendment right to free speech, (b) comply with the ADA and

section 504 by not acquiescing to stereotypical fears concerning a student with a

mental health disability who is in treatment and presents no risk to others, and (3)

respect the public process developed by the school district by which Portland

residents select a high school.” Id. at 19. Meanwhile, Ms. Doe asserts “[t]here is no

public interest that supports denial of injunctive relief in this case.” Id.

B. Portland Public Schools’ Opposition

In response, Portland Public Schools contends the “Court should not exercise

its extraordinary injunctive power to substitute its judgment for the judgment of

experienced, school administrators about the best educational and safety interests of

PPS students.” Def.’s Opp’n at 1. PPS argues that the record “reveals that, based on

all the information made known to school officials, PPS’s re-entry plan for John is

eminently reasonable in light of all students’ interests, including those of John.” Id.

at 2.

1. Likelihood of Success on the Merits

PPS maintains that because Ms. Doe “has failed to show a substantial

likelihood of success on the merits and because all other remaining factors compel

denial of [her] requested relief, this Court must deny [her] request for a preliminary

injunction and temporary restraining order.” Id. at 20.

To start with, PPS argues Ms. Doe’s First Amendment challenge will fail on

the merits. Id. at 6-14. First, PPS claims Ms. Doe’s legal argument “grossly

oversimplifies the nexus between the PHS community and John’s speech,” “overlooks

the other relevant facts known to PPS as well as [PPS’s] practical obligation to act

proactively to protect the entire PHS community.” Id. at 7. Second, PPS argues “the

First Amendment gives leeway for schools to regulate the speech at issue here, which

was in the form of text messages that constituted harassment and threats aimed at

specific individuals. Contrary to Plaintiff’s argument, this leeway remains true

regardless of whether the speech here occurred on campus or off.” Id. PPS continues,

arguing that “because written statements can be regulated by the school under

Tinker, Plaintiff’s arguments regarding true threats are inapposite.” Id. (referencing

Tinker v. Des Moines Indep. Comm. Sch. Dist., 393 U.S. 503 (1969)).

Even if Tinker controls, PPS argues, any regulation of John Doe’s speech was

permissible because “there was actual disruption on school premises,” it was

“reasonable—and arguably obligatory—for school officials to anticipate a disruption,”

and “John Doe’s text messages invaded the rights of other students ‘to be secure and

to be let alone.’” Id at 9-10 (quoting Tinker, 393 U.S. at 508). Moreover, PPS

contends, the “disruptions and invasions on the rights of other students were caused

by John sending these text messages to other students” and PPS’ response was

“eminently reasonable in light of the information known to the school

administrators.” Id. at 11.

Parsing the argument even further, PPS argues that even if the Court found

John Doe’s speech was off-campus speech, the speech at issue here qualifies as

“serious or severe bullying or harassment targeting particular individuals and

“threats aimed at teachers or other students,” Mahanoy, 141 S. Ct. at 2045, therefore

qualifying as “speech for which schools maintain their ability to regulate student

speech even if it was “off-campus.” Defs.’ Opp’n at 12 (citing Doe v. Hopkinton Pub.

Sch., 19 F.4th 493, 505-06 (1st Cir. 2021) (“The Supreme Court made clear in

Mahanoy . . . that schools have a significant interest in regulating ‘serious or severe

bullying or harassment’ that invades the rights of others . . . . This pedagogical

interest remains even in off-campus circumstances.”)).

PPS turns to Ms. Doe’s ADA and Rehabilitation Act claims and argues they

similarly will not succeed on the merits. To succeed under either act, a plaintiff must

“show that his or her disability is the cause of his alleged exclusion from a program

or service.” Def.’s Opp’n at 15 (citing 42 U.S.C. § 12132 (“[N]o qualified individual

with a disability shall, by reason of such disability, be excluded from participation in

or be denied the benefit of the services, programs, or activities of a public entity, or

be subjected to discrimination by any such entity.”) and 29 U.S.C. § 794(a) (“No

otherwise qualified individual with a disability . . . shall, solely by reason of her or

his disability, be excluded from the participation in, be denied the benefits of, or be

subjected to discrimination under any program or activity receiving Federal financial

assistance . . . .”)) (emphasis in Def.’s Opp’n). PPS contends that plaintiff cannot

establish John’s disability was the but-for cause of the involuntary school transfer

because “the evidence makes plain that . . . PPS’s actions have been in response to

John’s conduct and the [Comprehensive School Threat Assessment Guidelines] threat

evaluation, not based on or even in response to John’s disability.” Def.’s Opp’n at 17.

To buttress this claim, PPS points to John’s actions since February 2023, which

include:

text messages to fellow students alluding to committing to “mass

murder and rape,” Townsend Decl. ¶ 15; describing plans to commit

sexual violence against an identified female student, Townsend Decl., ¶

15; taken a knife with him to track practice, Townsend Decl. ¶ 18;

harassed female students, including female cross country team

members, Townsend Decl. ¶ 20; Obare Decl. ¶ 11; and circulated a

lengthy text message graphically narrating a fantasy of sexual violence

against a female classmate, and describing an “increased risk of murder

around” himself, Townsend Decl., Ex. 5.”

Defs.’ Opp’n at 17-18. PPS points to the fact that “PHS suspended and performed a

threat assessment on John in September 2023, in response to this concerning conduct,

before it even learned of John’s diagnoses in October,” Id. at 18 (internal citations

omitted), and argues that Ms. Doe “has not and cannot proffer any evidence that any

non-disabled student who engaged in such conduct would have been treated

differently than John has been and is being treated.” Id. Lastly, PPS argues that the

evidence belies Ms. Doe’s assertion that John’s transfer was in response to a

stereotypical expression of fear and discomfort by a small group of students. Id.

Instead, PPS contends, the transfer is in response to “student’s concerns based on

John’s concrete actions and threats, not an abstract or stereotype view of his mental

health struggles or diagnoses,” in conjunction with “school administrators’ and Dr.

Moran’s independent analysis of John’s actions and needs in order to move forward

as part of the PPS community.” Id.

2. Likelihood of Irreparable Harm

PPS argues that disruptions to John Doe’s athletic schedule “does not

constitute irreparable harm.” Id. at 19 (quoting Dziewa v. Penn. Interscholastic

Athletic Ass’n, Inc., No. CIV.A. 08-5792, 2009 WL 113419, at *7 (E.D. Pa. Jan. 16,

2009) and citing Sisson v. Va. High Sch. League, Inc., No. 7:10CV00530, 2010 WL

5173264, at *4 (W.D. Va. Dec. 14, 2010) and S.B. ex rel. Brown v. Ballard Cty. Bd. of

Educ., 780 F. Supp. 2d 560, 569 (W.D. Ken. 2011)).

PPS then argues Ms. Doe’s failure to identify any concrete college recruitment

or collage opportunities that would be impacted by John’s transfer make that

potential harm too speculative and therefore “not the kind of harm that preliminary

injunctions were fashioned to address.” Id. (quoting Dziewa, 2009 WL 113419, at *7).

PPS disputes that John’s transfer will damage his twelfth-grade experience

because “courts ‘routinely hold that a student suffers no irreparable harm where the

[school district] provides an alternative educational option and where the student can

stay on track to graduate.’” Id. (citing McKinney ex rel. K.P. v. Huntsville Sch. Dist.,

350 F. Supp. 3d 757, 771 (W.D. Ark. 2018) (collecting cases)). PPS contends, to the

contrary, that “a transfer to Casco Bay High School would likely benefit John’s

academic studies, because PHS’s social environment is so saturated with rumors

about John (both true and false) that are disruptive and distracting to John’s

schoolwork.” Id. at 20.

3. Balance of the Equities

PPS does not explicitly address the balance of the equities other than in its

introduction and conclusion. However, from these references the Court gleans PPS’s

contention that the interests to be balanced are those of John Doe and the “safety and

education of all students.” Id. at 1 (emphasis in original). See also id. at 20 (“PPS is

steadfast in its commitment to delivering a safe and stable learning environment for

all students while simultaneously balancing its obligation to protect the rights of all

students”).

4. Public Interest

PPS disputes Ms. Doe’s assertion that there is “no public interest that supports

denial of injunctive relief in this case.” See id. at 20. It posits that Ms. Doe “ignores

the interests of the entire PHS community, which includes both students and staff,

who have been spending significant time and resources away from instructional time

to manage students’ reactions and concerns about John,” id., and that “[t]he students

at PHS who have been the subject or recipient of John’s explicit threats of violence,

including sexual violence targeted at specific female students, will feel unsafe if he is

allowed to return to PHS.” Id.

C. Ms. Doe’s Reply

First, Ms. Doe argues the case continues to warrant urgent consideration and

entry of a temporary restraining order because the roster submission deadline for the

New England championship meet to be held on November 11, 2023 is this Sunday,

November 5, 2023. Pl.’s Reply at 3. Since PPS has no intention of adding John to the

roster, Ms. Doe asks the Court to compel them to do so. Id.

Ms. Doe maintains she is likely to prevail on the merits. Id. She takes issue

with PPS’s position, as Ms. Doe articulates it, that “having an administrator say that

John’s off-campus speech requires his voluntary transfer because it would support

the ‘safety, health and well-being of John and the school munity,’ means no First

Amendment analysis is necessary.” Id. at 3-4. Ms. Doe disagrees, “emphasizing that

all of John Doe’s ‘behavior’ in this case is in the form of off-campus speech,” id. at 4,

diminishing “the leeway the First Amendment grants to schools to regulate speech.”

Id. (citing Mahanoy, 141 S. Ct. at 2046). Therefore, John should “retain a right to

speak free of government interference or sanction unless that speech runs afoul of the

test recently set forth in Mahanoy Area Sch. Dist., v. B.L., 141 S. Ct. 2038 (2021).”

Id.

Instead of applying the Tinker “on-campus speech test” that “does not apply,”

Ms. Doe contends PPS must “justify its involuntary transfer of John by proving

‘serious or severe bullying or harassment targeting particular individuals’ or ‘threats

aimed at teachers or other students.’” Id. (citing Mahanoy, 141 S. Ct. at 2045). Ms.

Doe does not believe PPS can do so, and says PPS is “dredging up” off-campus speech

to sanction John, thereby violating his First Amendment rights. Id. at 4-5.

Ms. Doe also finds PPS’s arguments that they can transfer John under the

Tinker test unavailing, taking issue with Ms. Doe citing two “on-campus speech”

cases that predate Mahanoy. Id. at 5 (referring to Norris v. Cape Elizabeth Sch. Dist.,

969 F.3d 12 (1st Cir. 2020) and LaVine v. Blaine Sch. Dist., 257 F.3d 981, 989 (9th

Cir. 2001)). Ms. Doe contends “[t]hese cases are not relevant to John’s off-campus

speech and do not control in this case.” Id. Instead, the “test set forth in Mahanoy is

the appropriate standard.” Id. Under this Mahanoy test, John’s speech “which does

not rise to the level of a true threat” should be considered protected speech. Id. (citing

Counterman v. Colorado, 143 S. Ct. 2106 (2023) (finding that a true threat is a

“serious expression conveying that a speaker means to commit an act of unlawful

violence”)).

Ms. Doe then argues John would suffer irreparable injury because

“[i]nvoluntary transferring John from PHS would cause him to miss out on [his goal

of competing in the cross-country National meet] and impact his college recruiting

prospects.” Id. at 6. Moreover, “transferring in the middle of his senior year would

undoubtably raise questions that would jeopardize his chance of admission. It would

also interrupt his academic experience.” Id. Lastly, Ms. Doe asserts PPS states

“without support, that John’s academics would not be disrupted.” Id. But in fact, she

argues, this “contradicts the recommendation of Dr. Ostrander” and “disregards the

significant possibility that John will not be able to continue in the same academic

classes at another school.” Id.

IV. LEGAL STANDARD

The procedural posture of this case falls between a motion for a TRO and a

motion for a preliminary injunction. TROs allow courts to provide emergency relief

on an ex parte basis and to “preserve the status quo until there is an opportunity to

hold a hearing on the application for a preliminary injunction.” 11A CHARLES ALAN

WRIGHT, ARTHUR R. MILLER & MARY KAY KANE, FEDERAL RULES OF CIVIL PROCEDURE

§ 2951, at 253 (2d ed. 1995). Preliminary injunctions are “issued to protect plaintiff

from irreparable injury and to preserve the court’s power to render a meaningful

decision after a trial on the merits.” Id. § 2947, at 121 (2d ed. 1995). TROs may be

granted with or without notice to the adverse party, though they must comply with

Rule 65(b) if they are granted without notice. Id. at 253-54; FED. R. CIV. P. 65(b).

Preliminary injunctions will, in the usual case, “be decided only after the parties have

presented testimony in support of their respective positions,” although Rule 65 does

not explicitly require a hearing. 11A WRIGHT, MILLER & KANE § 2949, at 220.

Here, PPS was given notice and an opportunity to respond, but the timing of

the Ms. Doe’s motion precluded an evidentiary hearing, forced PPS to file her the

following day after receiving notice of the motion, and required the Court to issue this

Order the day after receiving the Plaintiffs’ reply brief.4

The standard for issuing a temporary restraining order is the same as for a

preliminary injunction and is provided by traditional equity doctrines. Aftermarket

Auto Parts Alliance, Inc. v. Bumper2Bumper, Inc., Civil No. 1:12-cv-00258-NT, 2012

U.S. Dist. LEXIS 143685, *3 (D. Me. Oct. 4, 2012); 11A WRIGHT, MILLER & KANE §

2942, at 37. To obtain preliminary injunctive relief, whether a temporary restraining

order or a preliminary injunction, the plaintiff must demonstrate: 1) “a likelihood of

success on the merits, 2) a likelihood of irreparable harm [to the movant] absent

interim relief, 3) a balance of equities in the plaintiff’s favor, and 4) [that the

preliminary injunctive relief would be in] service of the public interest.” Arbojet, Inc.

v. Rainbow Treecare Sci. Advancements, 749 F. 3d 168, 171 (1st Cir. 2015).

As the moving party, the plaintiff “bears the burden of establishing that these

four factors weigh in its favor.” Esso Standard Oil Co. v. Monroig-Zayas, 445 F.3d

4 In ruling on the motion as quickly as possible, the Court has done its level best, but the parties

should appreciate “the temporal constraints under which the district court labored.” See Bl(a)ck Tea

Soc’y v. City of Boston, 378 F.3d 8, 15 (1st Cir. 2004).

13, 18 (1st Cir. 2006). “A preliminary injunction is an extraordinary and drastic

remedy that is never awarded as of right.” Peoples Federal Savings Bank v. People’s

United Bank, 672 F.3d 1, 8-9 (1st Cir. 2012) (quoting Voice of the Arab World, Inc. v.

MDTV Med. News Now, Inc., 645 F.3d 26, 32 (1st Cir. 2011)). While “trial courts have

wide discretion in making judgments regarding the appropriateness of” preliminary

injunctive relief, Sanchez v. Esso Std. Oil Co., 572 F.3d 1, 14 (1st Cir. 2010), it is well

established “that the Court is to bear constantly in mind that an injunction is an

equitable remedy which should not be lightly indulged in, but used sparingly and only

in a clear and plain case.” Saco Defense Sys. Div. Maremont Corp. v. Weinberger, 606

F. Supp. 446, 450 (D. Me. 1985).

V. DISCUSSION

Because Ms. Doe has alleged three different claims, each of which if

meritorious would independently weigh in favor of the Court granting injunctive

relief, the Court addresses the likelihood of success on the merits of the First

Amendment claim and the two disability discrimination claims before addressing the

remaining preliminary injunctive relief factors.

A. Likelihood of Success on the Merits

The First Circuit has observed that likelihood of success on the merits is both

the “sine qua non” and the “most important part of the preliminary injunction

assessment,” explaining that “if the moving party cannot demonstrate that he is

likely to succeed in his quest, the remaining factors become matters of idle curiosity.”

Sindicato Puertorriqueño de Trabajadores v. Fortuño, 699 F.3d 1, 7, 10 (1st Cir. 2012)

(quoting Jean v. Mass. State Police, 492 F.3d 24, 27 (1st Cir. 2008), and New Comm

Wireless Servs. Inc. v. Sprintcom, Inc., 287 F.3d 1, 9 (1st Cir. 2002)). To carry their

burden on this factor, the Plaintiffs “must establish a ‘strong likelihood’ that they will

ultimately prevail.” Id. at 10 (quoting Respect Maine PAC v. McKee, 622 F.3d 13, 15

(1st Cir. 2010)).

1. First Amendment Claim

The Supreme Court has made “clear that students do not ‘shed their

constitutional rights to freedom of speech or expression,’ even ‘at the school house

gate.’” Mahanoy, 141 S. Ct. at 2044 (quoting Tinker, 393 U.S. 503, 506 (1969)); accord

Brown v. Entertainment Merchants Assn., 564 U.S. 786, 794 (2011) (“[M]inors are

entitled to a significant measure of First Amendment protection”) (alteration in

original; internal quotation marks omitted). In fact, “[t]he vigilant protection of

constitutional freedoms is nowhere more vital than in the community of American

schools.” Tinker, 393 U.S. at 512 (quoting Shelton v. Tucker, 364 U.S. 479, 487

(1960)).

But the Supreme Court has also “made clear that courts must apply the First

Amendment ‘in light of the special characteristics of the school environment.’”

Mahanoy, 141 S. Ct. at 2044 (quoting Hazelwood School Dist. v. Kuhlmeier, 484 U.S.

260, 266, (1988) (internal quotation marks omitted)). “One such characteristic . . . is

the fact that schools at times stand in loco parentis, i.e., in the place of parents.” Id.

(citing Bethel School Dist. No. 403 v. Fraser, 478 U.S. 675, 684 (1986)). The Court

has also specifically “outlined three specific categories of student speech that schools

may regulate in certain circumstances include: 1) indecent, lewd, or vulgar speech

uttered during a school assembly on the school grounds; 2) speech, uttered during a

class trip, that promotes illegal drug use; and 3) speech that others may reasonably

perceive as bearing the imprimatur of the school, such as that appearing in a school-

sponsored newspaper.” Mahanoy, 141 S. Ct. at 2045 (quoting Bethel School Dist., 478

U.S. at 685 and Morse v. Frederick, 551 U.S. 393, 409 (2007) and Kuhlmeier, 484 U.S.

at 271) (cleaned up). Finally, in Tinker, the Supreme Court said “schools have a

special interest in regulating speech that ‘materially disrupts classwork or involves

substantial disorder or invasion of the rights of others.’ Mahanoy, 141 S. Ct. at 2045

(quoting Tinker, 393 U.S. at 513).

All these “special characteristics call for special leeway when schools regulate

speech that occurs under its supervision.” Id. While schools’ license to regulate

speech is at its highest when it occurs on campus, it does not disappear simply

because speech occurs off campus. Id. Instead, a “school's regulatory interests

remain significant in some off-campus circumstances.” Id. In fact, Tinker specifies

that “conduct by the student, in class or out of it, which for any reasons—whether it

stems from time, place, or type of behavior . . . is not immunized by the constitutional

guarantee of free speech” if leads to material disruption, substantial disorder, or the

invasion of the rights of others. Tinker, 393 U.S. at 513. The Supreme Court, in

Mahanoy, explicitly refused to delineate “what counts as ‘off campus’ speech and

whether or how ordinary First Amendment standards must give way off campus to a

school’s special need to prevent, e.g., substantial disruption of learning-related

activities or the protection of those who make up a school community.” Mahanoy, 141

S. Ct. at 2045. This refusal was because of how fact-specific this inquiry ultimately

is. See id. However, the Supreme Court’s reference to the Tinker factors made clear

that “Tinker’s highly general statement about the nature of a school’s special

interests” remained good law and implies that there are indeed times when “First

Amendment standards must give way off campus to a school’s special need to prevent”

some on-campus ramifications of said off-campus speech. See id; accord Chen

Through Chen v. Albany Unified Sch. Dist., 56 F.4th 708, 719-720 (9th Cir. 2022), cert.

denied sub nom. Epple v. Albany Unified Sch. Dist., 143 S. Ct. 2641 (2023) (holding a

three-factor test considering “the degree and likelihood of harm to the school caused

augured by the speech, (2) whether it was reasonably foreseeable that the speech

would reach and impact the school, and (3) the relation between the content and

context of the speech and the school” was consistent with Mahanoy).

The Supreme Court went on to “mention three features of off-campus speech

that often, even if not always, distinguish schools’ efforts to regulate that speech from

their efforts to regulate on-campus speech,” thereby diminishing “the strength of the

unique educational characteristics that call for special First Amendment leeway.” Id.

at 2046. These three diminishing features are 1) that schools rarely stand in loco

parentis off-campus, 2) “courts must be more skeptical of a school’s efforts to regulate

off-campus speech,” and 3) schools have “an interest in protecting a student’s

unpopular expression, especially when the expression takes place off campus.” Id.

These factors fit comfortably with an application of the factors outlined in Tinker. Cf.

Chen Through Chen, 56 F.4th at 719-720 (holding the additional specific

considerations that the Court identified in Mahonay fit comfortably within the three-

factor framework).

With that explication of the parameters outlined by the Supreme Court on

cases where the school’s, or school district’s, interest in regulating First Amendment

speech is allowed, the Court now turns to the fact-intensive inquiry in the present

case, which is “at the outer boundaries as to when courts should apply school speech

precedents.” Morse v. Frederick, 551 U.S. 393, 401 (2007) (citing Porter v. Ascension

Parish School Bd., 393 F.3d 608, 615 n.22 (5th Cir. 2004)).

The parties’ countervailing arguments set out why this case is on the outer

boundary. On the one hand, Ms. Doe argues, accurately, that PPS’s “basis for John’s

involuntary transfer consists only of off-campus speech in the form of private text

messages to peers that were later forwarded to the school.” Pl.’s Mot. at 11. On the

other hand, PPS accurately argues that Ms. Doe’s legal argument “oversimplifies the

nexus between the PHS community and John’s speech.” Defs.’ Opp’n at 7. That is to

say, the present facts fall in the increasing group of scenarios where a student’s off-

campus speech manages to have very real on-campus ramifications. Citing Mahanoy,

Doe accurately argues that John’s speech being off campus diminishes “the leeway

the First Amendment grants [the school district] to regulate speech.” Pl.’s Reply at 4

(citing Mahanoy, 141 S. Ct. at 2046).

Again relying on Mahanoy, Ms. Doe argues the Tinker “on-campus speech test”

“does not apply.” Id. at 4 (citing Mahanoy, 141 S. Ct. at 2045). However, in Tinker,

the Supreme Court explicitly stated that “conduct, by the student, in class or out of

it, which for any reasons—whether it stems from time, place, or type of behavior . . .

is not immunized by the constitutional guarantee of free speech” if leads to material

disruption, substantial disorder, or the invasion of the rights of others. Tinker, 393

U.S. at 513 (emphasis supplied).

This leaves the Court unpersuaded that Tinker only applies to on-campus

speech. On the very page that Ms. Doe cites in Mahanoy, the Supreme Court

disavows that the special characteristics discussed in Tinker “disappear when a

school regulates speech that takes place off campus.” Mahanoy, 141 S.Ct. at 2045.

In fact, the Supreme Court goes on to say that “[t]he school’s regulatory interests

remain significant in some off-campus circumstances.” Id. (emphasis supplied). The

Court, in line with Supreme Court precedent, holds that the Tinker factors are not

applicable only when on-campus speech is being regulated.

Ms. Doe, having taken issue with Tinker, offered that the “test set forth in

Mahanoy is the appropriate standard.” Pl.’s Reply at 5. However, the Supreme Court

did not forth a test in Mahanoy. The Mahanoy Court explicitly refused to do so.

Mahanoy, 141 S. Ct. at 2045 (“Thus, we do not now set forth a broad, highly general

First Amendment rule stating just what counts as “off campus” speech and whether

or how ordinary First Amendment standards must give way to a school’s special need

to prevent, e.g., substantial disruption of learning-related activities or the protection

of those who make up a school community.”) (emphasis supplied). Instead, the

Supreme Court opted to “mention three features of off-campus speech that often, even

if not always, distinguish schools’ efforts to regulate that speech from their efforts to

regulate on-campus speech.” Id. at 2046. These three diminishing features are 1)

that schools rarely stand in loco parentis off-campus, 2) “courts must be more

skeptical of a school’s efforts to regulate off-campus speech,” and 3) schools have “an

interest in protecting a student’s unpopular expression, especially when the

expression takes place off campus.” Id. The Court agrees that these three features

diminish PPS’s ability to regulate John’s speech, but they are to be considered

alongside the Tinker factors, as a supplement. Guided by the Supreme Couret, the

Court, therefore, uses the diminish features in that way. See id.

If Tinker controls, as the Court finds that it does, PPS argues that any

regulation of John Doe’s speech was permissible because “there was actual disruption

on school premises,” it was “reasonable—and arguably obligatory—for school officials

to anticipate a disruption,” and “John Doe’s text messages invaded the rights of other

students ‘to be secure and to be let alone.’” Id at 9-10 (quoting Tinker, 393 U.S. at

508). The Court, after reviewing the full record before it, agrees. While any one of

these Tinker factors would be enough to allow the school district’s curtailing of John’s

free speech, all three are present here.

The Court begins with actual disruption of school premises. PPS provides

multiple pieces of evidence showing such a disruption. John’s lengthy sexualized

message, references a female peer as the object of his sexual desire, and describing

her increased risk of murder when around him, was “displayed on a phone and passed

around a class by students so that it was viewed by every student in the room.”

Townsend Decl. ¶ 17. It was later “shared by students during the school day.” Id. It

is hard to see how this would not disrupt classroom instruction, the core mandate of

PPS is tasked with.

While Ms. Doe emphasizes that the messages by John were meant to “private,”

his efforts failed. “Given the ease with which electronic communications may be

copied or shown to other persons, it was plainly foreseeable” these communications

“would ultimately hit their targets, with resulting significant impacts to those

individual students and to the school as a whole.” Chen, 56 F.4th at 720-21 (citing

D.J.M. ex rel. D.M. v. Hannibal Pub. Sch. Dist. No. 60, 647 F.3d 754, 762 (8th Cir.

2011) (upholding school discipline against D.J.M. for private instant messages to

C.M. that contained threats towards classmates, stating that “a reasonable person

should be aware that electronic communications can now be easily forwarded” and

that, “[s]ince C.M. was a classmate of the targeted students, D.J.M. knew or at least

should have known that the classmates he referenced could be told about his

statements”). Although not binding, the Court accepts the persuasive value of these

decisions given how analogous these cases are to the present facts.

“Mahanoy makes clear, the mere fact that a student's off-campus

communication finds its way to the school is not alone sufficient to warrant regulation

by school officials.” Chen, 56 F.4th at 720 (citing 141 S. Ct. at 2047 (invalidating

school's discipline over B.L.'s off-campus speech despite the fact that she used a

medium that clearly “risk[ed] transmission to the school itself”)). However, given the

facts here, it was “reasonable—and arguably obligatory—for school officials to

anticipate a disruption” if John were allowed to return to campus as if his text

messages were normal communication between peers. Defs.’ Opp’n at 9-10 (quoting

Tinker, 393 U.S. at 508). Several students spoke to the school administrators about

their concerns about John. Obare Decl. ¶ 6. Others expressed harm about John

harming himself, harming others, and failing to respect boundaries with females as

exemplified by him repeatedly saying things like “I know where you live” or “I can

find where you live” as well as repeatedly calling and contacting them, at times

discussing sexual material. Id. ¶¶ 7-10. “A total of five female students have

requested that the school prohibit John from having contact with them.” Id. ¶ 11.

For students to face the daily presence of another student who has threatened them

clearly disrupts the intended functioning of a place of learning. Based on this record,

the Court concludes that it is reasonable for PPS to have believed, and acted on the

belief, that John returning to the school would continue to “materially disrupt[]

classwork or involve substantial disorder.” Tinker, 393 U.S. at 513. His presence at

the school and the off-campus messages he sent already caused such disruption and

disorder.

Finally, even if neither of these Tinker factors were persuasive—which they

are—PPS may regulate John’s speech because it qualifies as “serious or severe

bullying or harassment,” which Mahanoy specifically identifies as an “off-campus

circumstance[ ]” in which “[t]he school's regulatory interests remain significant.” 141

S. Ct. at 2045; accord Doe v. Hopkinton Pub. Sch., 19 F.4th 493, 505-06 (1st Cir. 2021)

(“The Supreme Court made clear in Mahanoy . . . that schools have a significant

interest in regulating ‘serious or severe bullying or harassment’ that invades the

rights of others . . . . This pedagogical interest remains even in off-campus

circumstances”). Again, regardless of John’s intention, there are several recorded

instances of his speech making others, particularly female students legitimately feel

harassed.

Merriam-Webster defines “harass” as “to annoy persistently” or “to create an

unpleasant or hostile situation for especially by uninvited and unwelcome verbal or

physical conduct.” Harass, MERRIAM-WEBSTER, https://www.merriam-webster.com/

dictionary/harassment (last updated Oct. 23, 2023). Similarly, the Oxford English

Dictionary as “[t]o subject (a person or group) to unwarranted . . . speech or behavior

causing annoyance, alarm, distress, or intimidation, usually persistently over a

period of time.” Harass, OXFORD ENGLISH DICTIONARY, https://www.oed.com/

dictionary/harass v?tab=meaning and use#2041087 (last visited Nov, 3, 2023).

Black’s Law Dictionary likewise defines harassment as “[w]ords, conduct, or action

(usually repeated or persistent) that, being directed at a specific person, annoys,

alarms, or causes substantial emotional distress to that person and serves no

legitimate purpose.” Harassment, BLACK’S LAW DICTIONARY (11th ed. 2019).

Under all these definitions, the Court finds that John’s communications

constitute harassment. John has, among other things, sent texts to classmates that

suggest he knows where they live and that he wants to commit violent acts. These

communications understandably created fear and apprehension on the part of their

recipients. Therefore, the Court finds that PPS can also regulate John’s speech under

the third Tinker factor.

Having found that Tinker controls, and that PPS was justified in regulating

John’s speech under any of the three Tinker factors, the Court concludes that PPS’

regulation of John’s speech was permissible and not a violation of John’s First

Amendment rights. Therefore, Ms. Doe has failed to carry her burden of showing a

likelihood of success on the merits with respect to her claim that PPS violated John’s

First Amendment rights.

2. Ms. Doe’s Claims Under Section 504 Claim of the

Rehabilitation Act of 1973 and Title II of the Americans

with Disabilities Act

Under section 504 of the Rehabilitation Act of 1973, “[n]o otherwise qualified

individual with a disability in the United States . . . shall, solely by reason of her or

his disability, be excluded from participation in, be denied the benefits of, or be

subjected to discrimination under any program or activity receiving Federal financial

assistance.” 29 U.S.C. § 794(a). Title II of the Americans with Disabilities Act (ADA)

is similar, providing that “no qualified individual with a disability shall, by reason of

such disability, be excluded from participation in or be denied the benefits of the

services, programs, or activities of a public entity, or be subjected to discrimination

by any such entity.” 42 U.S.C. § 12132. Because of the similarities between the two

statutes, the First Circuit has held that the “same standards . . . apply to claims under

the ADA and under the rehabilitation Act.” Calero-Cerezo v. U.S. Dep’t of Just., 355

F.3d 6, 11 n.1 (1st Cir. 2004). Under this joint standard, a party seeking relief must

establish that (1) “he is a qualified individual with a disability,” (2) “he was excluded

from participating in, or denied the benefits of a public entity’s services, programs, or

activities or was otherwise discriminated against,” and (3) “such exclusion, denial of

benefits, or discrimination was by reason of his disability.” Kiman v. N.H. Dep’t of

Corr., 451 F.3d 274, 283 (1st Cir. 2006).

Here, the parties disagree about whether Ms. Doe has shown that the decision

to prohibit John from returning to PHS was made “by reason of his disability.” Ms.

Doe accuses PPS of ordering John’s “involuntary transfer in response to a

stereotypical expression of fear and discomfort by a small group of students at PHS.”

Pl.’s Mot. at 16. PHS counters that its “actions have been in response to John’s

conduct and the CSTAG threat evaluation, not based on or even in response to John’s

disability.” Def.’s Opp’n at 17.

After reviewing the evidence, the Court finds that Ms. Doe has failed to show

that PPS acted “by reason of” John’s disability. The return-to-school plan shared with

Ms. Doe and John by PPS states that John was found to have violated three PPS

policies. Defs.’ Opp’n at 9. These policies prohibit “[v]iolent, threatening or menacing

behavior,” “verbal or written statements (including those made on or through a

computer or other electronic device) which threaten, intimidate, or harass others,”

and harassment of students based on sex and gender, among other things. Townsend

Decl. ¶¶ 8-11. While it is true that five female students also expressed discomfort at

the prospect of John returning to PHS, this does not negate PPS’ finding that John’s

actions violated district policy. As PPS has maintained, “PHS’s actions are not based

solely on those students’ expressions of fear or discomfort, but rather on school

administrators’ and Dr. Moran’s independent analysis of John’s actions and needs in

order to move forward.” Defs.’ Opp’n at 18.

Given the language in John’s communications, Ms. Doe has not presented any

evidence to negate PPS’ assertions that it formulated John’s return-to-school plan

based at least in part on its conclusions that John’s conduct violated district policy.

Therefore, the Court does not find that PPS’ decision to prohibit John from returning

to PHS was made by reason of John’s disability. There is ample evidence in the record

that this decision was made because of John’s conduct. Thus, the Court finds that

Ms. Doe has failed to carry her burden of showing that she is likely to succeed on the

merits of her Rehabilitation Act and ADA claims.

B. Likelihood of Irreparable Harm

Plaintiffs seeking preliminary relief must demonstrate “that irreparable injury

is likely in the absence of an injunction.” Winter, 555 U.S. at 22 (emphasis in original).

“[I]rreparable harm can consist of ‘a substantial injury that is not accurately

measurable or adequately compensable by money damages.’” Ross-Simons of

Warwick, Inc. v. Baccarat, Inc., 217 F.3d 8, 13 (1st Cir. 2000) (Ross-Simons II)

(quoting Ross-Simons of Warwick, Inc. v. Baccarat, Inc., 102 F.3d 12, 19 (1st Cir.

1996) (Ross-Simons I)). “[D]istrict courts have broad discretion to evaluate the

irreparability of alleged harm.” Ross-Simons II, 217 F.3d at 13 (quoting K-Mart Corp.

v. Oriental Plaza, Inc., 875 F.2d 907, 915 (1st Cir. 1989)).

Ms. Doe argues that, in the absence of preliminary relief, John will suffer

irreparable harm due to (i) loss of educational opportunities, (ii) loss of athletic

opportunities, and (iii) disruptions in the college application and recruiting process.

The Court disagrees that these considerations, alone or together, rise to the level of

irreparable harm.

Courts have found that the complete deprivation of educational opportunities

constitutes irreparable harm. See Johnson v. Collins, 233 F. Supp. 2d 241, 251-52

(D.N.H. 2002) (“The loss of Andrew’s right to a free public education, and its likely

impact on his future opportunities, is not accurately measurable or adequately

compensable by money damages”); Brown v. Bd. of Educ. of Rochester City Sch. Dist.,

No. 04-CV-6596L, 2005 WL 17838, at *1 (W.D.N.Y. 2005) (“The longer Nicholas’s

expulsion continues, the longer he will be deprived of a formal education. Courts

have held that such a deprivation of one’s education inflicts harm that cannot be

remedied by money damages”). The denial of the opportunity to attend one’s school

of choice has likewise been found to constitute irreparable harm when accompanied

by a deprivation of procedural due process. See Murphy v. Fort Worth Indep. Sch.

Dist., 258 F. Supp. 2d 569, 575 (N.D. Tex. 2003), vacated on other grounds, 334 F.3d

470 (5th Cir. 2003) (“Carter will suffer irreparable injury if such an injunction is not

granted. He would be denied, without having had his procedural due process rights

recognized, the valuable right to continue his education at his home school”).

In the absence of an alleged due process violation, however, courts “routinely

hold that a student suffers no irreparable harm where the District provides an

alternative educational option and where the student can stay on track to graduate.”

McKinney ex rel. K.P. v. Huntsville Sch. Dist., 350 F. Supp. 3d 757, 771 (W.D. Ark.

2018); cf. Axelrod v. Phillips Academy, Andover, 36 F. Supp. 2d 46, 50 (D. Mass. 1999)

(finding that the plaintiff would suffer irreparable harm “because he would not

graduate with his class, he could not attend college in the fall, and he would suffer

the stigma of expulsion”).

“Courts have routinely rejected the notion that a student suffers irreparable

harm by not being permitted to participate in interscholastic athletics.” McGee v. Va.

High Sch. League, Inc., 801 F. Supp. 2d 526, 531 (W.D. Va. 2011); see also Dziewa v.

Pa. Interscholastic Ath. Ass’n, No. 08-5792, 2009 U.S. Dist. LEXIS 3062, at *17-18

(E.D. Pa. Jan 16, 2009) (“This Court, as well as all other federal courts, have

previously and consistently held that ineligibility for participation in interscholastic

athletic competitions alone does not constitute irreparable harm”); S.B. ex rel. Brown

v. Ballard Cty. Bd. of Educ., 780 F. Supp. 2d 560, 569 (W.D. Ky. 2011) (rejecting

plaintiff student’s argument that forced transfer to an alternative school for

disciplinary reasons would inflict irreparable harm in the form of exclusion from

playing on original school’s softball team).

Likewise, “courts reject the notion that loss of a potential scholarship may

constitute irreparable harm.” McKinney ex rel. K.P. v. Huntsville Sch. Dist., 350 F.

Supp. 3d 757, 771 (W.D. Ark. 2018). This is particularly true where the party seeking

preliminary injunctive relief has failed present evidence of concrete scholarship

opportunities. See Dziewa, 2009 U.S. Dist. LEXIS 3062 at *18-19 (finding that

plaintiffs did not show irreparable harm due to potential negative impacts on

recruiting opportunities because such “arguments consist of threatening possibilities,

which are speculative, and not the kind of harm that preliminary injunctions were

fashioned to address”).

Here, Ms. Doe has failed to carry her burden of demonstrating that John will

suffer irreparable harm absent the issuance of a TRO. The Court agrees with the

other courts that have considered the issue that an inability to participate in

interscholastic athletics, and the resulting negative impacts on college recruiting, do

not amount to irreparable harm. This is particularly true where, as here, PPS has

not prohibited John from running track and cross-country altogether. It has only

determined that John may not run for PHS. While John may prefer to run for PHS,

the Court finds that an inability to run for PHS, standing alone, cannot rise to the

level of irreparable harm. Further, although it is true that John may have to explain

to college coaches and athletic departments why he no longer runs for PHS, this

potential consequence is exactly the type of speculative harm the Dziewa court

rejected. See Dziewa, 2009 U.S. Dist. LEXIS 3062 at *18-19. Therefore, the Court

holds that John cannot show irreparable harm based on an inability to run for PHS

and the potential consequences that might have for college recruiting.

This leaves Ms. Doe’s argument that John will suffer irreparable harm if he

transfers to Casco Bay or Deering High Schools based on a loss of educational

opportunities. Ms. Doe represents that John “has worked hard to craft an academic

schedule at PHS that would permit him to earn the credits needed for graduation,

capture all the prerequisites for college programming he seeks to pursue, [and]

complete his carpentry certification.” Pl.’s Mot. at 17. She also suggests that there

is a “significant possibility that John will not be able to continue in the same academic

classes at another school.” Pl.’s Reply at 6. PPS, on the other hand, has represented

that “John will be able to receive comparable instruction at either Casco Bay High

School or Deering High School to what he would have received at Portland High

School.” Townsend Decl. ¶ 40.

The record is murky as to how John’s transfer to either Casco Bay High School

or Deering High School would affect his education. It seems clear enough that John

would continue to receive an education at either alternative school. Further, neither

party has suggested that John would not be able to graduate on time were he to

transfer to a different school. Indeed, PPS has even represented that John has been

working with his teachers and a tutor during his suspension. See Doe Decl. ¶ 31 (“He

is invested in his current PHS classes and has been working with his teachers, tutor,

and senior planning advisor to complete all his work”). In the absence of any evidence

to the contrary, then, the Court will assume that John will be able to graduate on

time even if he changes schools as required by his return-to-school plan.

Given that John seems to be able to graduate on time, and has not alleged a

violation of due process, this situation appears more akin to those in which courts

have declined to find irreparable harm. See McKinney ex rel. K.P. v. Huntsville Sch.

Dist., 350 F. Supp. 3d 757, 771 (W.D. Ark. 2018). There is, however, one more wrinkle

to consider: the PATHS Program. It is also unclear from the record whether John

will be able to complete his carpentry certification in conjunction with coursework at

Casco Bay High School and/or Deering High School. Likewise, it is unclear whether

PATHS is part of John’s curriculum, or something he does in addition to his required

coursework.

Given that Ms. Doe bears the burden of showing that John will suffer

irreparable harm absent a TRO, however, the Court resolves this evidentiary

ambiguity in favor of PPS. It may be that John will be able to complete the PATHS

program even if he leaves PHS. Even if John can devote the same amount of time to

PATHS during the school day, moreover, it may be possible for him to make up the

time after school hours. As it stands, the record suggests that John will be able to

graduate on time under his return-to-school plan, and he may even be able to

complete the PATHS Program as well. Therefore, based on this record, the Court is

unable to conclude that John will suffer irreparable harm absent a TRO.

C. Balance of Equities

When considering whether to grant preliminary injunctive relief, the Court

must weigh the balance of equities to determine whether the injury to the plaintiff in

the absence of a TRO outweighs any harm to the defendant. Ms. Doe contends that

John would suffer sever harm absent a TRObecause PPS’ re-entry plan amounts to a

“termination of his programming and affiliation with PHS during his senior year,

needlessly damag[ing] his college recruiting opportunities and plac[ing] his mental

health at risk.” Pl.’s Mot. at 18. Further, she contends that PPS would suffer “[l]ittle,

if any harm” were the Court to grant preliminary injunctive relief, because “(a) John

poses no risk of harm to students or staff at PHS, (b) he has agreed to abide by the

terms of the District Court’s stipulated protection from harassment order and the

recommendations in Portland’s psychological report, and (c) the return to PHS

promises to have therapeutic benefits for John.” Id. at 19. After reviewing the record

before it, the Court finds this to be an oversimplification.

PPS has put forth considerable evidence concerning the impact of John’s

actions on the students and staff at PHS. John’s peers have repeatedly reported to

school administrators concerning text messages sent by John. See Townsend Decl.

¶ 15. PHS administrators have reported that such messages have caused

“substantial disruption within the school,” including one message being “displayed

one a phone and passed around the class so that it was viewed by every student in

the room.” Obare Decl. ¶¶ 3-4. Students at PHS have expressed concern that John’s

statements, and “some female students . . . have expressed anxiety over their

perception that John does not respect boundaries.” Id. ¶¶ 8-11. Furthermore, John’s

has prompted the PHS cross-country coach to inform the school’s athletic director

that he no longer wants John on his team because of John’s “sexually harassing

behavior and threats toward female team members.” Townsend Decl. ¶ 20. Assistant

Principal Obare confirmed that she has “heard several times from the coach of the

[cross-country] team about his concern for the emotional well-being of the team” as a

result of John’s conduct. Obare Decl. ¶ 12.

Based on this record, John’s return to school would likely cause substantial

disruptions for other students and staff at PHS. It may have a particularly negative

impact on those students who have expressed concerns for their safety, especially

those on the cross-country team. Given the distinct possibility that widespread

negative effects would result from John’s return to PHS, the Court disagrees with

Ms. Doe’s contention that the balance of equities weighs in favor of granting a TRO.

While the Court understands Ms. Doe’s concern about John’s mental health being

negatively impacted by a transfer to a different high school, the potential effects of

John’s return to PHS on the mental health of many of his classmates counsels in favor

of denying the request for a TRO based on the balance of equities.

D. Public Interest

“The public interest factor requires this Court to inquire whether there are

public interests beyond the private interests of the litigants that would be affected by

the issuance or denial of injunctive relief.” Everett J. Prescott, Inc. v. Ross, 383 F.

Supp. 2d 180, 193 (D. Me. 2005). “In exercising their sound discretion, courts of equity

should pay particular regard for the public consequences in employing the

extraordinary remedy of injunction.” Winter, 555 U.S. at 24. Ms. Doe asserts that

the public interest “weighs in favor of requiring” PPS to (i) “honor John’s First

Amendment right to free speech,” (ii) “comply with the ADA and section 504 by not

acquiescing to stereotypical fears concerning a student with a mental health

disability who is in treatment and presents no risk to others,” and (iii) “respect the

public process developed by the school district by which Portland residents select a

high school.” Pl.s Mot. at 19. PPS counters that granting preliminary injunctive

relief would go against its interested in creating a stable educational environment for

all students. Def’s Opp’n at 20.

The Court agrees with PPS that the public interest favors the denial of

injunctive relief in this case. As PPS has stated, the provision of a safe educational

environment for all students is the paramount obligation of a school board. This

obligation outweighs the public interest in adherence to the process for choosing a

high school, which, presumably, is subordinate to the obligation to provide a stable

school environment. Therefore, the Court finds that the public interest favors denial

of preliminary injunctive relief.

VI. CONCLUSION5

The Court DENIES the Plaintiff’s Motion for Temporary Restraining Order

(ECF No. 4). The Court reserves ruling on the motion for preliminary injunction and

will discuss future proceedings with counsel at the conference scheduled for

November 6, 2023.

SO ORDERED.

/s/ John A. Woodcock, Jr.

JOHN A. WOODCOCK, JR.

UNITED STATES DISTRICT JUDGE

Dated this 3rd day of November, 2023

5 Given the urgency of this order and its contents, the Court is issuing this order under seal for

the moment. The Court will discuss with counsel the extent to which the order should be unsealed,

perhaps with some redactions. See United States v. Kravetz, 706 F.3d 47 (1st Cir. 2013).