# Kupperstein v. Baker

> District Court, D. Massachusetts · July 21, 2021

URL: https://www.frixlaw.com/law-library/cases/10199624

## Case

- **Court:** District Court, D. Massachusetts
- **Decided:** July 21, 2021
- **Opinion:** 100trialcourt
- **Cited by:** 0 later opinions in the Frix Law Library

## Citator (automated)

- No negative treatment found by the automated citator. That is not the same as a confirmation that the case is good law; read the citing cases.
- Full citator and citing cases: https://www.frixlaw.com/law-library/cases/10199624

## How later opinions describe it (automated extraction)

- noting that to state such a claim, a plaintiff must allege, among other things, “that the actor intended to inflict emotional distress or that he knew or should have known that emotional distress was the likely result of his conduct”
- declining to treat with leniency pro se litigant who was an attorney

## Opinion text

UNITED STATES DISTRICT COURT
DISTRICT OF MASSACHUSETTS
_______________________________________
)
DONALD C. KUPPERSTEIN, )
)
Plaintiff, )
)
v. ) Civil Action No.
) 20-11868-FDS
CHARLES D. BAKER, in his official )
capacity as Governor of Massachusetts; )
RICHARD J. MCMAHON; MARYLOU )
SUDDERS, Secretary of the Executive )
Office of Health and Human Services; )
DANIEL TSAI, Director of the Office of )
Medicaid; RHONDA MACLEOD; and )
AUSTIN MCHOUL, )
)
Defendants. )
_______________________________________)
MEMORANDUM AND ORDER ON
DEFENDANTS’ MOTIONS TO DISMISS
SAYLOR, C.J.
This action arises out of a dispute that has been the subject of at least three other court
proceedings. Plaintiff Donald C. Kupperstein, an attorney proceeding pro se, asserts claims
against defendants Charles D. Baker, Governor of Massachusetts; Richard J. McMahon,
Associate Justice of the Probate and Family Court; Marylou Sudders, Secretary of the Executive
Office of Health and Human Services; Daniel Tsai, Assistant Secretary for MassHealth and
Director of the Office of Medicaid; Rhonda MacLeod, a revenue manager at University of
Massachusetts Medical School; and Austin McHoul, an attorney. The amended complaint
purports to assert claims under 42 U.S.C. §§ 1983, 1985(2), and 1985(3) for violation of
plaintiff’s constitutional rights and for various state-law torts.
The underlying facts are set forth in detail in several other judicial opinions, including In
re Kupperstein, 943 F.3d 12 (1st Cir. 2019) (“Kupperstein I”) and In re Kupperstein, 994 F.3d
673 (1st Cir. 2021), petition for cert. filed (“Kupperstein II”).1 As described by the First Circuit,
the basic facts are as follows.
Donald Kupperstein, “with the help of his comrade, Thomas Sheedy, improperly
entangled himself with a piece of real property on Reservoir Street in Norton, Massachusetts[,]

and lined his pockets with rents from various tenants he installed.” 994 F.3d at 674.
“Kupperstein . . . and Sheedy duped the only child of Fred Kuhn, the property’s owner, after
Kuhn's death, into selling the property for a ‘pittance.’” Id. at 674 n.1. “That property belonged
to the estate of Fred Kuhn . . . and that estate owed a debt to the Massachusetts Office of Health
and Human Services, better known as ‘MassHealth.’” Id. at 675. “Ultimately, the probate court
voided the property’s transfer (so that Kupperstein and Sheedy had no claim to it) and ordered
the duo to pay to MassHealth ‘any and all’ rents collected from the property.” Id. “Kupperstein
and Sheedy disregarded the probate court’s order and continued to rent the property for their own
gain.” Id.

Kupperstein subsequently filed a bankruptcy petition in an effort to retain the property
and avoid the contempt sanctions, which was not successful. Id. at 675-76. As of November
2019, “[Kupperstein had] defied seven state court orders, four arrest warrants, and a mountain of
contempt sanctions.” Kupperstein I, 943 F.3d at 15.
Kupperstein has now filed suit against the governor, a justice of the Probate and Family
Court, and various other state officials and a private attorney. Defendants have filed three

1 Judicial decisions are subject to judicial notice to establish the “procedural history of the case,” but not to
establish the “truth of [the] facts recited therein.” Lopes v. Riendeau, 177 F. Supp. 3d 634, 667 (D. Mass. 2016)
(quoting Jonas v. Gold, 627 F. App’x 134, 139 (3d Cir. 2015)). The facts set forth in the opinions of the First
Circuit are generally consistent with those set forth in the amended complaint. However, to the extent they are
inconsistent, this Court will not consider them, and will accept the allegations in the amended complaint as true.
separate motions to dismiss the amended complaint, all contending that it fails to state a claim
upon which relief can be granted. Defendants McHoul and MacLeod also contend that the
claims against them are barred by issue preclusion.
For the reasons stated below, defendants’ motions to dismiss will be granted.
I. Background

Unless otherwise noted, the following facts are drawn from the amended complaint, and
from documents referred to by the amended complaint or attached to it.2
A. Parties
Donald C. Kupperstein is an attorney who is licensed to practice in Massachusetts. (Am.
Compl. ¶ 14).
Charles D. Baker is the Governor of Massachusetts. (Id. ¶ 15). Richard J. McMahon is
an Associate Justice of Bristol County Probate and Family Court (the “Probate Court”). (Id. ¶
16). Marylou Sudders is the Secretary of the Executive Office of Health and Human Services.
(Id. ¶ 17). Daniel Tsai is the Assistant Secretary for MassHealth and the Director of the Office
of Medicaid. (Id. at 1; id. ¶ 18). Rhonda MacLeod is a revenue manager at the University of
Massachusetts Medical School. (Id. ¶ 19). Austin McHoul is an attorney. (Id. ¶ 35).

2 On a motion to dismiss, a court may properly take into account four types of documents outside the
complaint without converting the motion into one for summary judgment: (1) documents of undisputed authenticity;
(2) documents that are official public records; (3) documents that are central to plaintiff’s claim; and (4) documents
that are sufficiently referred to in the complaint. Watterson v. Page, 987 F.2d 1, 3 (1st Cir. 1993).
Defendant McHoul attached the following records to his motion to dismiss: (1) an April 20, 2016 order of
Suffolk Superior Court (Exhibit 1); (2) a November 29, 2016 order of the Probate Court (Exhibit 2); (3) a December
22, 2017 order of the Probate Court (Exhibit 8); and (4) a April 12, 2018 order of the Probate Court (Exhibit 9).
Those documents are sufficiently referred to in the complaint for the Court to consider them. (See Am. Compl. at 34
n. 24 (citing to “EOHHS v. Estate of Kuhn, et als, Suffolk Superior at Page 1”); id. ¶ 157 (quoting from the Dec. 22,
2017 order); id. ¶ 244 (quoting from the Nov. 29, 2016 order); id. ¶¶ 162, 188 (referring to the content, although not
referencing the date, of the April 12, 2018 order)). They are also matters of public record. Giragosian v. Ryan, 547
F.3d 59, 66 (1st Cir. 2008) (noting that “[a] court may consider matters of public record in resolving a Rule 12(b)(6)
motion to dismiss” and that “[m]atters of public record ordinarily include documents from prior state court
adjudications”) (internal quotation marks omitted).
B. Factual Background
In 2009, Fred W. Kuhn began accepting Medicaid payments from the Executive Office of
Health and Human Services (“EOHHS”). (Id. ¶ 31). It was not reimbursed for those payments.
At some point, to secure the debt, totaling $191,746.79, it recorded a lien on a property of his
located at 346 Reservoir Street in Norton, Massachusetts. (Id. ¶¶ 31, 50, 58, 60-61, 115, 233).

On September 17, 2013, Kuhn passed away. (Id. ¶ 32). His daughter, Carol Thibodeau,
became the personal representative of his estate. (Id. ¶¶ 37, 39(a), 39(b)). She retained an
attorney, Austin McHoul, to represent the estate in probate proceedings in the Probate Court.
(Id. ¶¶ 35, 162).3 Upon probate of the will, which the court approved on March 27, 2014,
Thibodeau became the owner of the Reservoir Street property. (Id. ¶¶ 36, 40, 50).
On November 21, 2014, Thibodeau conveyed the property to Thomas Sheedy. (Id. ¶¶ 65,
69). Thibodeau received “less than $100” and a “tax redemption of $3,379.13” in exchange for
the property. Kupperstein I, 943 F.3d at 16. Kupperstein prepared, notarized, and recorded the
deed, which listed the “redemption information and [other] consideration” on it. (Am. Compl. ¶¶
64, 66, 73-74).

According to the amended complaint, Kupperstein loaned Sheedy money to pay for
services, labor, and materials for improvements to the property. (Id. ¶¶ 2, 91). On November
22, 2014, to secure the loan, he recorded a mechanics lien against the property. (Id. ¶¶ 92-93,
185).
On June 4, 2015, a prospective buyer, Claire Boyle, signed an agreement to purchase the
property. (Id. ¶ 87). However, “prior to June 5, 2015,” McHoul told Clark, her attorney, that

3 As the First Circuit noted, MassHealth is empowered to recover benefits from a beneficiary’s estate after
death and, in this case, filed a petition with the Massachusetts Probate Court to ensure payment. See Mass. Gen.
Laws ch. 118E, §§ 31, 32; Kupperstein II, 994 F.3d at 675 n.2.
Sheedy’s title to the property was “no good,” and Boyle, through Clark, repudiated the
agreement. (Id. ¶¶ 85-87).4
On July 7, 2015, EOHHS filed a verified complaint against Kupperstein, among others,
in Suffolk Superior Court. (Id. ¶¶ 97-98). The complaint appears to allege that Tsai and Sudders
were responsible for the filing of that complaint, and its contents, because of their positions as

Assistant Secretary for MassHealth, and Secretary of the EOHHS, respectively. (Id. ¶¶ 17, 18,
214; id. ¶ 25 (noting that “the Terms ‘DMA’, ‘EOHHS’ and ‘MassHealth’ refer to Scudders [sic]
and Tsai”)). MacLeod verified the complaint. (Id. ¶¶ 98-103). It contended that the transfer of
the property to Sheedy was invalid because of the EOHHS lien and because a notice of claim had
been filed against the estate. (Id. ¶ 217).
According to the amended complaint, on April 20, 2016, the Superior Court ruled that
EOHHS held a valid lien on the property, but left the sale intact, and dismissed a count of fraud.
(Id. ¶ 5). In addition, it entered judgment in Kupperstein’s favor on counts seeking (1) a
declaratory judgment that Thibodeau’s transfer of the property was “unenforceable because it

was done without authorization from the Probate Court”; (2) “rescission of the deed transferring
the Property to Sheedy [] on th[at] same ground,” (McHoul Supp. Mem., Ex. 1 (“Apr. 20, 2016
Order”) at 4); and (3) treble damages pursuant to Mass. Gen. Laws ch. 118E. (Am. Compl. ¶¶
109, 111, 219; see also Apr. 20, 2016 Order at 4). Nevertheless, the Court noted that
“Thibodeau’s sale to Sheedy notwithstanding, the Property may still be subject to a petition in
Probate Court seeking a license to sell the Property to satisfy the Estate’s debt to HHS, and this
court can make no ruling as to the Property’s status in that regard.” (Apr. 20, 2016 Order at 5 n.3

4 On July 7, 2015, Boyle apparently filed a civil action against Kupperstein in Bristol Superior Court
seeking specific performance of their agreement. (Am. Compl. ¶ 89). According to the amended complaint, “[o]n
Kupperstein’s motion for summary judgment, Bristol Superior dismissed all claims brought against Kupperstein,
individually, or in any other capacity.” (Id. ¶ 90).
(noting that Mass. Gen. Laws ch. 202, § 20 “defin[es] the conditions under which real property
of an estate that has been sold by an heir or devisee may be subject to sale in order to satisfy the
debts of an estate”)).
On May 17, 2016, EOHHS filed a petition against the estate in the probate proceedings in
the Probate Court seeking payment or a forced sale of the property to satisfy Kuhn’s debt. (Am.

Compl. ¶ 115). Kupperstein filed an objection to the petition on the grounds that he was an
interested party. (Id. ¶ 241). On November 29, 2016, Judge McMahon, an associate justice of
that court, ruled that the transfer of the property to Sheedy was invalid and that the property was
still part of Kuhn’s estate. (Id. ¶ 8; see also McHoul’s Supp. Mem., Ex. 2 (“Nov. 29, 2016
Order”)). Among other things, Judge McMahon ordered that “[n]either [] Sheedy nor []
Kupperstein . . . shall execute or record any further documents concerning [the property] without
further order of this Court” and that “[a]ny and all rents received by . . . Kupperstein . . . prior to
the date of this Order shall be made payable to EOHHS.” (Am. Compl. ¶¶ 146, 244).5 The
decision noted that “The Objector and the Respondent, Donald C. Kupperstein, did not appear

for the hearing [on the motion for summary judgment],” but nevertheless cited to several of
Kupperstein’s arguments. (Nov. 29, 2016 Order at 1, 3, 4).
At some point, it appears that EOHHS filed a complaint for contempt against
Kupperstein. (Am. Compl. ¶ 148; id. at 46 (attaching an undated complaint for civil contempt
filed by EOHHS)). The complaint for civil contempt claimed that an exhibit attached to it—
which is not attached to the amended complaint—“show[ed] monthly rent and late fees collected

5 It appears from the complaint that at some point the premises were leased to tenants. (See, e.g., Am.
Compl. ¶ 178 (“EOHHS knew that Kupperstein received no funds from rental of the Property”); id. ¶ 159 (quoting
from an e-mail Kupperstein wrote to McHoul on January 4, 2018, stating that “the tenants have agreed to give
[McHoul] a key.”)).
by [Kupperstein], totaling $33,150 due to EOHHS.” (Id. at 46).6 On August 4, 2017, “after [a]
hearing,” Judge McMahon ruled that Kupperstein was in contempt of court for
“willfully . . . neglect[ing] and refus[ing] to pay any and all rents received from the subject
premises to plaintiff in the amount of $33,150.00” and ordered that he must “pay [the estate] the
sum of $33,150.00 . . . within [] 60 days of the date of this order.” (See Am. Compl. at 44-45

(attaching that Aug. 4, 2017 order to the complaint)).
On December 22, 2017, “after [a] hearing,” Judge McMahon held Kupperstein in
contempt of court for “willfully . . . neglect[ing] and refus[ing] to comply with the orders and
judgments of the Court relative to the subject premises” and ordered that he must surrender the
premises, and pay over any sums in rent to the estate, among other items. (McHoul Supp. Mem.,
Ex 8 (“Dec. 22, 2017 Order”) at 1). He also ordered Kupperstein to be committed to jail for 30
days, or to pay $5,400 to purge the contempt, but suspended the sentence until March 9, 2018.
(Id.; Am. Compl. ¶ 157 (quoting from the order of contempt)).
On January 11, 2018, Kupperstein filed a bankruptcy petition under Chapter 7 and listed
the Reservoir Street property as his property. (Am. Compl. ¶¶ 148, 184-85).7 He did not obtain

6 “Mid-way through 2017, Sheedy passed off his claimed ownership to Kupperstein . . . who kept collecting
rent.” Kupperstein I, 943 F.3d at 17. The amended complaint does not directly address that transfer, but implies
that at some point Kupperstein became the owner. (See, e.g., Am. Compl. ¶ 185 (noting that Kupperstein listed his
interest in the property on a bankruptcy petition); id. ¶ 159 (including e-mails between McHoul and Kupperstein
about the lease agreement for the property and turning over the keys)).
7 A petition for bankruptcy typically activates an automatic stay of judicial, administrative, or other
proceedings against the debtor. 11 U.S.C. § 362(a). However, the bankruptcy court found “‘good cause’ to ‘lift[]’
the stay and ordered that the state court actions could proceed, except that Schall [the estate’s representative] and
MassHealth [EOHHS] could ‘not seek to enforce against . . . Kupperstein, any judgment with respect to the
$191,741.79 MassHealth reimbursement claim . . . .’” Kupperstein II at 676. It also denied a motion by
Kupperstein to hold EOHHS in contempt and to impose sanctions against it, finding that “state court actions that
‘involved the imposition and enforcement of sanction awards against [Kupperstein] did not violate the automatic
stay’ and, therefore, neither did MassHealth’s [EOHHS’s] participation in those proceedings.” Id. at 676-77
(quoting the bankruptcy court’s decision) (emphasis added).
Kupperstein appealed those decisions to the district court, and when MassHealth moved to dismiss his
appeal based on the “‘fugitive disentitlement doctrine’ —the rule that a fugitive (usually a criminal one) forfeits the
right to appeal the judgment (usually a conviction) he[] [is] fleeing”—the district court granted the motion.
Kupperstein I at 15-16. Kupperstein appealed that decision to the First Circuit. Id. at 16-17. Although the First
permission from the Probate Court to do so, and EOHHS filed a second complaint for civil
contempt in that court. (Id. ¶¶ 148, 187). On January 12, 2018, Judge McMahon held a hearing
on the complaint and found Kupperstein in contempt.
On April 12, 2018, Judge McMahon ordered that Kupperstein be committed to 30 days in
jail for his failure to surrender control of the property to Kuhn’s estate, for listing the property as

an interest on the bankruptcy filing, (id. ¶¶ 148, 162, 188), and for “illegally collecting []
rent . . . in direct violation of th[e] Court’s several orders including its order dated November 29,
2016 and its Order on Contempt dated August 4, 2017.” (McHoul Supp. Mem., Ex 9 (“Apr. 12,
2018 Order”) ¶ 3). The sentence was suspended until May 18, 2018. (Id. ¶ 12). Kupperstein
alleges that that sentence was a violation of his constitutional rights because “McMahon had
been informed [that] Kupperstein did not have [a key].” (Am. Compl. ¶ 162).
According to the amended complaint, on March 31, 2020, Judge McMahon sentenced
Kupperstein to an additional 60-day commitment. The amended complaint does not specify the
reasons for that sentence. (Id. ¶¶ 140, 253).8

C. Procedural Background
On October 16, 2020, Kupperstein filed a complaint in this court against Governor Baker
and Judge McMahon. On January 22, 2021, he filed an amended complaint, adding counts
against defendants Sudders, Tsai, MacLeod, and McHoul.

Circuit noted that it shared the district court’s concern for Kupperstein’s “serial misconduct and contempt for the
state courts,” it found that the dismissal had been premature, and remanded the case to the district court to render a
decision on the merits. Id. at 16.
On remand, the district court affirmed the bankruptcy court’s decision to lift the stay and to deny
Kupperstein’s motion for contempt and sanctions. Kupperstein II at 677 n.6. Kupperstein appealed that decision to
the First Circuit. Id. at 677. The First Circuit determined that the bankruptcy court had not abused its discretion in
lifting the stay or declining to hold MassHealth in contempt or levy sanctions against it, and that the district court
had properly affirmed the bankruptcy court’s decision. Id. at 682.
8 Following a March 2018 court date, Kupperstein missed the three following court dates in his case and
was held in contempt two more times. Kupperstein I, 943 F.3d at 18.
Among other things, Count One seeks a declaration that Judge McMahon “wrongfully
usurped jurisdiction over EOHHS’s May 17, 2016 petition” and an injunction preventing the
Probate Court from incarcerating Kupperstein absent further order of this Court. (Id. ¶¶ 16, 132,
139).9 Count Two alleges that Governor Baker is vicariously liable for the negligence of the
agents of EOHHS and of the Probate Court, and seeks relief against him on that basis under the

Massachusetts Tort Claims Act, Mass. Gen. Laws ch. 258, § 2. (Id. ¶¶ 15, 198). Count Three
alleges (1) a claim against all defendants under 42 U.S.C. § 1983 for violations of the Fourth,
Fifth, and Fourteenth Amendments due to Kupperstein’s incarceration and loss of property; and
(2) that defendants acted in concert in abridging Kupperstein’s procedural and substantive due
process rights and therefore violated 42 U.S.C. §§ 1985(2) and 1985(3). (Id. ¶ 260).10
Although not tied to enumerated counts, the amended complaint also alleges that Sudders
and Tsai negligently hired the lawyers who represented EOHHS in the state court proceedings at
issue here. (Id. ¶ 191). It further alleges that Judge McMahon, Sudders, Tsai, MacLeod, and
McHoul committed certain unspecified “common law torts” and that they “jointly and severally

injured Kupperstein, and directly and proximately caused Kupperstein to suffer financial harm,
damage to his reputation, and intentional infliction of emotional distress.” (Id. ¶¶ 16-20, 201,
260). Finally, it alleges that McHoul “tort[i]ously interfered with the Trust’s sale of the Property
to one Boyle, a Buyer who signed a [purchase and sale agreement] to acquire the [p]roperty.”
(Id. ¶ 257).
All of the defendants have filed motions to dismiss the amended complaint for failure to

9 Count One contains a demand for relief, but does not in fact allege any claim. The Court will therefore
consider it in connection with the other claims alleged against Judge McMahon.
10 Although Kupperstein has included multiple claims in Count Three, for clarity, the Court will
nevertheless refer to it as “Count Three.”
state a claim upon which relief can be granted, among other items. Defendants McHoul and
MacLeod also contend in their motions to dismiss that the claims against them are barred by
issue preclusion.
II. Standard of Review
To survive a motion to dismiss, a complaint must state a claim that is plausible on its

face. See Bell Atl. Corp. v. Twombly, 550 U.S. 544, 570 (2007). For a claim to be plausible, the
“[f]actual allegations must be enough to raise a right to relief above the speculative level . . . .”
Id. at 555 (internal citations omitted). “The plausibility standard is not akin to a ‘probability
requirement,’ but it asks for more than a sheer possibility that a defendant has acted unlawfully.”
Ashcroft v. Iqbal, 556 U.S. 662, 678 (2009) (quoting Twombly, 550 U.S. at 556).
In determining whether a complaint satisfies that standard, a court must assume the truth
of all well-pleaded facts and give plaintiffs the benefit of all reasonable inferences. See Ruiz v.
Bally Total Fitness Holding Corp., 496 F.3d 1, 5 (1st Cir. 2007) (citing Rogan v. Menino, 175
F.3d 75, 77 (1st Cir. 1999)). Dismissal is appropriate if the complaint fails to set forth “factual
allegations, either direct or inferential, respecting each material element necessary to sustain

recovery under some actionable legal theory.” Gagliardi v. Sullivan, 513 F.3d 301, 305 (1st Cir.
2008) (quoting Centro Medico del Turabo, Inc. v. Feliciano de Melecio, 406 F.3d 1, 6 (1st Cir.
2005)).
Where, as here, a party is proceeding pro se, any document he or she files “is to be
liberally construed, and a pro se complaint, however inartfully pleaded, must be held to less
stringent standards than formal pleadings drafted by lawyers.” Erickson v. Pardus, 551 U.S. 89,
94 (2007) (quoting Estelle v. Gamble, 429 U.S. 97, 106 (1976)) (internal quotation marks
omitted); see also Fed. R. Civ. P. 8(e) (“Pleadings must be construed so as to do justice.”). But
see Cintron-Lorenzo v. Departamento de Asuntos del Consumidor, 312 F.3d 522, 526-27 (1st
Cir. 2002) (declining to treat with leniency pro se litigant who was an attorney). However, while
pro se complaints “are accorded ‘an extra degree of solicitude’ . . . even a pro se plaintiff is
required to ‘set forth factual allegations, either direct or inferential, respecting each material
element necessary to sustain recovery under some actionable legal theory.’” Wright v. Town of
Southbridge, 2009 WL 415506, at *2 (D. Mass. Jan. 15, 2009) (quoting Adams v. Stephenson,

116 F.3d 464, at *1 (1st Cir. June 23, 1997) (per curiam)).
III. Analysis
A. Issue Preclusion
Defendants McHoul and MacLeod allege that issue preclusion prevents Kupperstein from
relitigating four issues that are central to his claims: (1) the validity of the MassHealth lien; (2)
the validity of the transfer of the property from Thibodeau to Sheedy; (3) whether Kupperstein
violated the orders of the Probate Court that resulted in the orders of contempt against him; and
(4) whether the orders of contempt in the Probate Court violated the automatic stay.11
Issue preclusion, also known as collateral estoppel, “bars parties from re-litigating issues
of either fact or law that were adjudicated in an earlier proceeding.” Robb Evans & Associates,
LLC v. United States, 850 F.3d 24, 31 (1st Cir. 2017). Issue preclusion requires three elements:

(1) a final judgment on the merits in the previous action; (2) the party against whom preclusion is
asserted was a party (or in privity with a party) to the prior action; and (3) the issues in the prior
and current adjudications are identical. Kobrin v. Bd. of Registration in Med., 444 Mass. 837,
843 (2005); Tuper v. N. Adams Ambulance Serv., Inc., 428 Mass. 132, 134 (1998). In addition,

11 Defendants Governor Baker, Tsai, Sudders, and Judge McMahon have not moved to dismiss the
amended complaint on the basis of issue preclusion. However, “even if [a party] waive[s] res judicata as an
affirmative defense, a court on notice that it has previously decided an issue may dismiss the action sua sponte,
consistent with the res judicata policy of avoiding judicial waste.” In re Medomak Canning, 922 F.2d 895, 904-05
(1st Cir. 1990); see also Arizona v. California, 530 U.S. 392, 412 (2000).
“[i]ssue preclusion can be used only to prevent relitigation of issues actually litigated in the prior
action” that were essential to the earlier judgment. Kobrin, 444 Mass. at 844.
“A nonparty may use collateral estoppel defensively against a party to the original action
who had a full and fair opportunity to litigate the issues in question.” Supeno v. Equity Office
Properties Mgmt., LLC, 70 Mass. App. Ct. 470, 473 (2007). “The guiding principle in

determining whether to allow defensive use of collateral estoppel is whether the party against
whom it is asserted ‘lacked full and fair opportunity to litigate the issue in the first action or
[whether] other circumstances justify affording him an opportunity to relitigate the issue.’” Alba
v. Raytheon Co., 441 Mass. 836, 841-42 (2004) (quoting Fidler v. E.M. Parker Co., 394 Mass.
534, 541 (1985)).
Here, to the extent Kupperstein’s claims are based on any of the four identified issues, he
is prevented from relitigating them.
The first issue is the validity of the MassHealth lien. The Superior Court found on April
20, 2016, that the MassHealth lien was valid in a memorandum and order on a motion for

summary judgment. (Apr. 20, 2016 Order at 7). Kupperstein was a defendant in that action, and
the issue of the validity of the lien was actually litigated and disputed. (Id. at 6 (“Defendants
contend that . . . the Lien was extinguished by operation of law and [EO]HHS therefore had no
valid interest in the Property.”)). The court concluded that there was nevertheless a genuine
issue of fact as to whether EOHHS was entitled to summary judgment as to its claim for unjust
enrichment, which requires a plaintiff to establish “not only that the defendant received a benefit,
but also that such a benefit was unjust,” among other items. (Id. at 8 (quoting Metro Life Ins. Co.
v. Cotter, 464 Mass. 623, 644 (2013)). It reached that conclusion because it found that “there
ha[d] been no determination by the Probate Court as to whether [EO]HHS [was] entitled to an
order compelling Thibodeau as personal representative to petition for a license to sell the
Property . . . and in any event, [EO]HHS appear[ed] still to hold the Lien on the Property.” (Id.).
Therefore, it was not clear “whether [EO]HHS’s ability to recover from the Property ha[d] or
ha[d] not been cut off, and therefore [] whether [] [Kupperstein] ha[d]or ha[d] not been enriched
at [EO]HHS’s expense.” (Id.).

Nevertheless, on November 27, 2018, on a second motion for summary judgment, the
court entered judgment in favor of EOHHS on the claim of unjust enrichment, among others.
(MacLeod Supp. Mem., Ex. 4 (“Nov. 27, 2018 Order”)). While the description of that judgment
is brief, a finding that the MassHealth lien was valid is essential to it, because otherwise any
benefit received by Kupperstein was not unjust. In addition, the court noted in its order of
judgment that it was taking judicial notice of “the findings . . . [from] its prior decisions in th[e]
case, in particular, [a] decision dated December 21, 2017 (Hallal, J.) which specifically [found]
that Kupperstein had actual notice of MassHealth’s lien and failed to pay it contrary to
MassHealth law.” (Id. at 1-2).12

The second issue is the validity of the transfer of the property from Thibodeau to Sheedy.
The Probate Court entered an order on November 29, 2016, that “Thibodeau executed an invalid
deed and improperly transferred the property to [] Sheedy.” (Nov. 29, 2016 Order ¶ 2).
Kupperstein objected to the petition, and the issue was actually litigated—although Kupperstein
did not appear for the hearing on the motion for summary judgment, in its order, the court noted
that “Kupperstein argues neither [] Thibodeau nor the Estate own the property located at 346

12 The November 29, 2016 ruling of the Probate Court also found that “upon Kuhn’s death, the property
remained an asset of the Estate of [] Kuhn and subject to EOHHS’[s] Chapter 118E lien.” (Nov. 29, 2016 Order at
3). However, in that action, “[t]he parties [did] not dispute that EOHHS placed and recorded a lien on the subject
property prior to [] Kuhn’s death.” (Id at 4). That could be because the Superior Court had already found that the
MassHealth lien was valid in its April 20, 2016 decision, but in any event, it is not clear that the issue was actually
litigated in the Probate Court action.
Reservoir Street.” (Id. at 3). In addition, that finding was essential to the judgment, which
granted EOHHS’s petition to force a sale of the property. (Id. ¶ 3). To force a sale of the
property, the court had to find that the property was still an asset of the estate, (id. ¶ 2 (“The
property . . . remains an asset of the Estate of Fred W. Kuhn.”), which in turn required a finding
that the transfer to Sheedy was invalid. (Id.).

The third issue is whether Kupperstein is prevented from relitigating whether he
committed the violations that resulted in the orders of contempt issued on August 4 and
December 22, 2017, and April 12, 2018.13 On August 4, 2017, Judge McMahon issued a
judgment of contempt against Kupperstein for “willfully . . . neglect[ing] and refus[ing] to pay
any and all rents received from the subject premises to plaintiff in the amount of $33,150.00.”
(See Am. Compl. at 44 (attaching that Aug. 4, 2017 order to the complaint)). On December 22,
2017, the court issued a judgment of contempt against Kupperstein because he had
“willfully . . . neglected and refused to comply with the orders and judgments of the Court
relative to the subject premises.” (Dec. 22, 2017 Order at 1; Am. Compl. ¶ 157 (quoting the Dec.

22, 2017 order of contempt)). On April 12, 2018, the court issued a judgment of contempt
because (1) Kupperstein had failed to surrender control of the property to Kuhn’s estate; (2) he
had listed the property as an interest on the bankruptcy filing, (Am. Compl. ¶¶ 148, 162, 188);
and (3) he had been “illegally collecting [] rent . . . in direct violation of th[e] Court’s several
orders including its order dated November 29, 2016 and its Order on Contempt dated August 24,
2017.” (Apr. 12, 2018 Order ¶ 3). Those were final judgments on the merits, to which
Kupperstein was a party, and the issues of whether he committed the violations in question were

13 As noted, the amended complaint alleges that there was another order of contempt on March 31, 2020,
but neither party has provided the court with a copy of that order.
essential to the finding of contempt. It also appears that the issues were actually litigated. The
orders refer to hearings that the Court held prior to finding Kupperstein in contempt, and he has
not alleged that he was not at those hearings or did not have notice of them.
The fourth issue is whether the orders of contempt in the Probate Court violated the
automatic stay. The Bankruptcy Court, the District Court, and the First Circuit all determined

that they did not, and therefore that Kupperstein’s motion for contempt and sanctions against
EOHHS for its participation in those proceedings should be denied. The First Circuit
summarized the issue as follows: “[t]he core dispute is whether the probate court’s contempt
proceedings and resultant penalties are excepted from the automatic stay (as the bankruptcy court
held they were) and therefore MassHealth’s participation [in them] did not merit sanctions . . . .”
Kupperstein II, 994 F.3d at 678-79. That issue was actually litigated and Kupperstein was a
party to the proceedings in question—he filed the motion for contempt and sanctions, and
appealed the bankruptcy court’s ruling on it. The issue of whether the contempt proceedings
violated the automatic stay was also essential to the bankruptcy court’s decision, because if the

proceedings did not violate the stay, then there was no basis on which to impose sanctions
against EOHHS. Moreover, an order on a motion for sanctions and contempt is a “judgment” for
purposes of issue preclusion. Cf. In re Keaty, 397 F.3d 264, 272-74 (5th Cir. 2005) (reversing
and remanding because issue preclusion should have been applied to appellate court’s imposition
of sanctions on a party’s motion for sanctions); Hirschfeld v. Spanakos, 104 F.3d 16, 19-20 (2d
Cir. 1997) (reversing and remanding because issue preclusion should have applied to appellate
court’s imposition of sanctions). And while Kupperstein has filed a petition for certiorari
seeking review of the First Circuit’s decision, a party is issue precluded even where “the first, or
issue preclusive, judgment is still on appeal when the second action occurs.” In re Kane, 254
F.3d 325, 328 (1st Cir. 2001); O’Brien v. Hanover Ins. Co., 427 Mass. 194, 200-01 (1998)
(adopting majority rule that “a trial court judgment is final and has preclusive effect regardless of
the fact that it is on appeal.”).
In summary, Kupperstein is barred from relitigating (1) the validity of the MassHealth
lien; (2) the validity of the transfer of the property from Thibodeau to Sheedy; (3) whether he

violated the orders of the Probate Court that resulted in the orders of contempt against him; and
(4) whether the orders of contempt in the Probate Court violated the automatic stay.
Accordingly, to the extent his claims are based upon those issues, they will be dismissed under
the doctrine of issue preclusion.
B. Claims under 42 U.S.C. § 1983
Count Three purports to assert a claim under 42 U.S.C. § 1983 for violations of
Kupperstein’s rights under the Fourth, Fifth, and Fourteenth Amendments. That section provides
a private cause of action against any “person” who, under color of state law, deprives another of
“any rights, privileges, or immunities secured by the Constitution and [federal] laws.” 42 U.S.C.
§ 1983. Therefore, to maintain a cause of action under section 1983, a plaintiff must allege,

among other things, a “deprivation of a federally secured right.” Harrington v. City of Nashua,
610 F.3d 24, 28 (1st Cir. 2010).
Kupperstein’s claim that his rights under the Fourth Amendment were violated appears to
be based on his allegation that he was “falsely imprison[ed].” (Am. Compl. ¶ 167); see Camilo–
Robles v. Hoyos, 151 F.3d 1, 6 (1st Cir. 1998) (“The right to be free from unreasonable seizure
(and, by extension, unjustified arrest and detention) is clearly established in the jurisprudence of
the Fourteenth Amendment (through which the Fourth Amendment constrains state action).”).
He also appears to allege that he was not afforded procedural due process before his
alleged property interest in the property was taken away from him, and he was deprived of
substantive due process because it was taken away from him. To state a valid substantive due
process claim, a complaint must allege that “[a plaintiff] suffered [a] deprivation of an
established life, liberty, or property interest, and that such deprivation occurred through
governmental action that shocks the conscience.” Clark v. Boscher, 514 F.3d 107, 112 (1st Cir.
2008). Similarly, an analysis of a procedural due-process claim proceeds in two steps: “We first

ask whether there exists a liberty or property interest of which a person has been deprived, and if
so we ask whether the procedures followed by the State were constitutionally sufficient.”
Swarthout v. Cooke, 562 U.S. 216, 219 (2011).
1. MacLeod
The complaint alleges that by signing the verified complaint filed in the Superior Court,
MacLeod deprived Kupperstein of his rights under the Fourth, Fifth, and Fourteenth
Amendments. (Am. Compl. ¶ 221).
To state a valid claim under section 1983, there must be “[a] deprivation of a right, [and]
a causal connection between the [defendant] and th[at] deprivation . . . .” Sanchez v. Pereira–
Castillo, 590 F.3d 31, 41 (1st Cir. 2009). In essence, MacLeod contends that the complaint does

not plausibly allege a causal connection between her and the alleged deprivations.
Causation under section 1983 is evaluated according to common-law tort principles. Id.
at 50. Under that approach, a defendant is deemed to have caused a person to be subjected to
constitutional deprivation if his or her actions “set[] in motion a series of acts by others which
the actor knows or reasonably should know would cause others to inflict the constitutional
injury.” Id. at 50-51 (quoting Gutierrez–Rodriguez v. Cartagena, 882 F.2d 553, 561 (1st Cir.
1989)). Thus, a defendant may be liable for “those consequences attributable to reasonably
foreseeable intervening forces, including the acts of third parties.” Sanchez, 590 F.3d at 51
(quoting Springer v. Seaman, 821 F.2d 871, 876 (1st Cir. 1987)).
The amended complaint contains only one allegation as to MacLeod—that she verified
the July 7, 2015 complaint in the Superior Court. That verified complaint alleged that the
transfer of the property was invalid because of the EOHHS lien, and because a notice of claim
had been filed against the estate. According to plaintiff, “when MacLeod verified the complaint,
she knew she swore falsely.” (Am. Compl. ¶ 221).

Although the Superior Court ruled that EOHHS held a valid lien on the property, its
ruling left the sale intact. (Id. ¶¶ 109, 111, 219). Thus, even assuming Kupperstein suffered a
deprivation of an established property interest, it is unclear how MacLeod’s verification of a
complaint in the Superior Court, which left the sale intact, caused that deprivation. In separate
proceedings, the Probate Court held that the transfer was void, and found Kupperstein in
contempt (which led to his incarceration). MacLeod is not alleged to have been a participant in
those proceedings or to have been involved in them in any way, nor does the amended complaint
allege that the Probate Court somehow relied upon the earlier findings of the Superior Court,
aside from noting that it had “indicated that EOHHS may petition for sale of the property in

Probate and Family Court.” (Nov. 29, 2016 Order at 3 (noting that the Superior Court had
indicated that EOHHS could petition for sale of the property in the Probate Court); Apr. 20, 2016
Order at 5 n.3). Accordingly, MacLeod did not “set[] in motion a series of acts by others which
[she] kn[ew] or reasonably should [have] know[n] would cause others to inflict the constitutional
injury.” Sanchez, 590 F.3d at 50-51 (quoting Gutierrez–Rodriguez, 882 F.2d at 561).
Furthermore, and in any event, Kupperstein is prevented from relitigating the issue of (1)
the validity of the MassHealth lien or (2) the validity of the transfer from Thibodeau to Sheedy,
and therefore, from contending that the complaint that MacLeod verified was false.
For those reasons, the claim under section 1983 as to MacLeod will be dismissed.
2. Judge McMahon
As noted, Judge McMahon is an Associate Justice of the Probate Court. (Am. Compl. ¶
16). Kupperstein alleges that the orders he issued during the proceedings in question deprived
him of his rights under the Fourth, Fifth, and Fourteenth Amendments.
“Absolute immunity from civil liability applies to any judicial officer for any normal and

routine judicial act.” Becks v. Plymouth County Superior Court, 511 F. Supp. 2d 203, 206 (D.
Mass. 2007). As long as the judge was performing “[a] judicial act[] within [his] jurisdiction,”
immunity will apply even if the judge “acted maliciously and corruptly in exercising
his judicial . . . functions” or “in the presence of grave procedural errors.” Goldstein v. Galvin,
719 F.3d 16, 24 (1st Cir. 2013) (internal quotations omitted).
The November 29, 2016 judgment that Judge McMahon issued on EOHHS’s complaint
for a forced sale of the property was clearly a “normal and routine judicial act,” Becks, 511 F.
Supp. 2d at 206. The orders of contempt that Judge McMahon issued were also clearly “normal
and routine.” Id. Judge McMahon is therefore entitled to judicial immunity as long as he was
performing acts “within [his] jurisdiction.” Goldstein, 719 F.3d at 24.

“[A] proceeding to enforce . . . [an] equitable lien, or in the alternative to obtain
compensation for the wrongful use of property subject to such a . . . lien, is within the scope of
general equity jurisdiction.” Locke v. Old Colony Tr. Co., 289 Mass. 245, 253 (1935). Pursuant
to Mass. Gen. Laws ch. 215, § 6, “[t]he probate and family court department [] [has] original and
concurrent jurisdiction with the supreme judicial court and the superior court department of all
cases and matters of equity cognizable under the general principles of equity jurisprudence and,
with reference thereto, [] [are] courts of general equity jurisdiction.” Mass. Gen. Laws ch. 215,
§ 6. Furthermore, Mass. Gen. Laws ch. 215, § 34 provides that “[p]robate courts shall have like
power and authority for enforcing orders . . . in the exercise of any jurisdiction vested in them,
and for punishing contempts of such orders . . . as are vested for such or similar purposes in the
supreme judicial or superior court in relation to an action in which equitable relief is sought
pending therein.” Mass. Gen. Laws. ch. 215, § 34.
The Probate Court therefore had jurisdiction over the May 17, 2016 petition because the
petition sought either payment for the lien or a forced sale of the property to satisfy a debt.

Judge McMahon also had jurisdiction to find plaintiff in contempt of his orders pursuant to
Mass. Gen. Laws ch. 215, § 34.14
Accordingly, Judge McMahon is entitled to judicial immunity, and the claim under
section 1983 will be dismissed against him on that basis.
3. Governor Baker
The claim under section 1983 is alleged against Governor Baker in his official capacity.
(Am. Compl. at 1; id. ¶ 15). As noted, that section provides a private cause of action against any
“person” who, under color of state law, deprives another of “any rights, privileges, or immunities
secured by the Constitution and [federal] laws.” 42 U.S.C. § 1983. However, a “person” under
section 1983 does not include state actors in their official capacities. Johnson v. Rodriguez, 943

F.2d 104, 108 (1st Cir. 1991) (“[N]either a state agency nor a state official acting in his [or her]
official capacity may be sued for damages in a section 1983 action.”). Accordingly, the amended
complaint fails to state a claim under section 1983 against Governor Baker on that basis.
The amended complaint also fails to state a claim under section 1983 because it does not
allege that any direct actions taken by Governor Baker caused the alleged harms. Rather, it
alleges that Tsai and Sudders, whom he appointed, caused the harms because (1) they were

14 As noted, the amended complaint also alleges that Judge McMahon issued another order of contempt on
March 31, 2020, but neither party has provided the court with that order, and Kupperstein has not alleged anything
beyond the fact of the order of contempt and 60-day commitment (which on its own, does not state a claim).
negligent in retaining the lawyers that prosecuted the lawsuits in question, and (2) they were
responsible for the filing of the July 7, 2015 complaint, and its contents—which Kupperstein
contends were false—because of their positions as Assistant Secretary for MassHealth, and
Secretary of the EOHHS, respectively. But “vicarious liability is inapplicable to . . . § 1983
suits.” Iqbal, 556 U.S. at 676; Brown v. Rhode Island, 511 F. App’x 4, 5 (1st Cir. 2013).

Accordingly, the claim under section 1983 as to Governor Baker will be dismissed.
4. Sudders and Tsai
The claim under section 1983 is alleged against Sudders and Tsai in their individual
capacities. (Am. Compl. ¶¶ 16-17). As noted, state officials sued in their individual capacities
may be held liable “only on the basis of their own acts or omissions.” Canales v. Gatzunis, 979
F. Supp. 2d 164, 171 (D. Mass. 2013). In addition, “mere negligence by [a] supervisor is not
enough to create liability [under section 1983].” Snell v. DeMello, 44 F. Supp. 2d 386, 390 (D.
Mass. 1999). State officials are liable under section 1983 only “when their own action or
inaction . . . amounts to gross negligence or deliberate indifference.” Guzman v. City of
Cranston, 812 F.2d 24, 26 (1st Cir. 1987) (internal quotations omitted).

The amended complaint contains two principal allegations against Sudders and Tsai.
First, it alleges that Sudders and Tsai “were negligent in retaining the lawyers who abused
process, trampled on plaintiff's civil rights under color of law, and acted to deprive plaintiff of
his property and his liberty, and of procedural and substantive due process.” (Am. Compl. ¶
191). It provides no specific factual allegations to support those assertions. It is therefore
entirely conclusory, and the court need not assume it is true. Iqbal, 556 U.S. at 681 (“[T]he
allegations are conclusory and not entitled to be assumed true.”). Moreover, “mere
negligence . . . is not enough,” and the amended complaint does not plausibly allege a set of facts
that they were grossly negligent or deliberately indifferent in retaining the lawyers in question.
Snell, 44 F. Supp. 2d at 390.
The amended complaint also alleges that Tsai and Sudders were responsible for the filing
of the July 7, 2015 and May 17, 2016 complaints, because of their positions as Assistant
Secretary for MassHealth, and Secretary of the EOHHS, respectively. (Am. Compl. ¶¶ 17, 18,
214; id. ¶ 25 (noting that “the Terms ‘DMA’, ‘EOHHS’ and ‘MassHealth’ refer to Scudders [sic]

and Tsai”)). Kupperstein contends that at least one of those complaints was “false[],” (id. ¶ 221),
apparently because “Scudders [sic], Tsai, MacLeod and McHoul knew that there was no
perfected creditor's claim on the Property because, under the MUPC [Massachusetts Uniform
Probate Code], the acts necessary to establish and perfect a creditor's claim had been time-
barred; and it was too late to re-open Kuhn's probate estate case.” (Id. ¶ 235).
Sudders and Tsai can only be held liable under section 1983 “on the basis of their own
acts or omissions,” and there are no allegations that they were in fact directly involved in the
filing of the complaint (only that they are responsible for it by virtue of their positions at
EOHHS). Gatzunis, 979 F. Supp. 2d at 171. In addition, as noted, Kupperstein is prevented

from relitigating the validity of the MassHealth lien or the transfer from Thibodeau to Sheedy,
and therefore from contending that the complaint was false due to a failure to perfect EOHHS’s
claim on the property.
Accordingly, the claim under section 1983 as to Tsai and Sudders will be dismissed.
5. McHoul
McHoul represented Kuhn’s estate in proceedings in the Probate Court. All of the
allegations against him in the amended complaint relate to that representation.
Because the statutory language, “under color of any statute, ordinance, regulation,
custom, or usage, of any State or Territory,” creates a state-action requirement, section 1983
rarely creates a right of action against private persons. See Aldrich v. Ruano, 952 F. Supp. 2d
295, 301 (D. Mass. 2013). It is also “well-settled that a lawyer (even a court-appointed one)
does not act under the color of state law in performing a lawyer’s traditional function as counsel
to a party.” Id. McHoul was thus not acting under color of state law by representing Kuhn’s
estate in the state-court proceedings. Accordingly, the claim under section 1983 as to McHoul
will be dismissed.

C. Claims under 42 U.S.C. §§ 1985(2) and 1985(3)
In addition to the claims under section 1983, Count Three purports to allege two other
similar but separate causes of action under 42 U.S.C. §§ 1985(2) and 1985(3).
Section 1985(2) creates a cause of action where “two or more persons conspire for the
purpose of impeding, hindering, obstructing, or defeating, in any manner, the due course of
justice in any State or Territory, with intent to deny to any citizen the equal protection of the
laws.” 42 U.S.C. § 1985(2). A claim under § 1985(3) requires proof of both a conspiracy and “a
conspiratorial purpose to deprive the plaintiff of the equal protection of the laws.” Perez–
Sanchez v. Pub. Bldg. Auth., 531 F.3d 104, 107 (1st Cir. 2008) (citing Aulson v. Blanchard, 83
F.3d 1, 3 (1st Cir. 1996)).

Sections 1985(2) and 1985(3) both require the complaint to plead that a race- or class-
based discriminatory motive lies behind the alleged conspirators’ actions. See Kush v. Rutledge,
460 U.S. 719, 725-26 (1983) (citing Griffin v. Breckenridge, 403 U.S. 88, 91 (1971)). Here, the
amended complaint fails to allege any facts establishing that plaintiff is a member of a protected
class or has suffered class-based discrimination.
In addition, the complaint does not plausibly allege with specificity any facts that, if true,
would support a finding of a conspiracy, or how defendants acted in concert to deprive
Kupperstein of his civil rights. (Am. Compl. ¶ 201); see Twombly, 550 U.S. at 555 (plaintiff's
obligation under Fed. R. Civ. P. 8(a) to provide the grounds of his claim “requires more than
labels and conclusions”); Dallas v. Holmes, 137 F. A’ppx 746, 752 (6th Cir. 2005) (per curiam)
(upholding dismissal under 28 U.S.C. § 1915(e)(2)(B) of claims under § 1983 that private
individuals conspired with law enforcement to perpetrate malicious prosecution: “Other than
general allegations of conspiracy to cause and influence a wrongful criminal prosecution,
Plaintiffs make no allegations of joint, concerted activity to deprive [plaintiff] of his civil

rights.”).
Thus, the claims under sections 1985(2) and 1985(3) will also be dismissed for failure to
state a claim.
D. State-Law Claims
The amended complaint purports to request certain relief pursuant to state law. Count
Two alleges that Governor Baker is vicariously liable for the negligence of the agents of EOHHS
and of the Probate Court, and seeks relief against him on that basis under the MTCA, Mass Gen.
Laws ch. 258, § 2. (Id. ¶¶ 15, 198). In addition, although not tied to enumerated counts, the
amended complaint alleges that Sudders and Tsai negligently hired the lawyers who represented
EOHHS in the actions at issue here. (Id. ¶ 191). It further alleges that Judge McMahon,

Sudders, Tsai, MacLeod, and McHoul committed certain unspecified “common law torts” that
“jointly and severally injured Kupperstein, and directly and proximately caused Kupperstein to
suffer financial harm, damage to his reputation, and intentional infliction of emotional distress.”
(Id. ¶¶ 16-20, 260).15 Finally, it alleges that McHoul “tort[i]ously interfered with the Trust’s sale
of the Property to []Boyle, a Buyer who signed a [purchase and sale agreement] to acquire the
property.” (Id. ¶ 257).

15 As noted, Count One contains a demand for relief, but does not in fact allege any claim. The Court will
therefore consider it in connection with the other claims alleged against Judge McMahon.
1. Governor Baker
The claim under the MTCA is alleged against Governor Baker in his official capacity.
(Am. Compl. at 1; id. ¶ 15). For purposes of sovereign immunity, suits for damages against state
officials in their official capacities generally constitute suits against the state itself. Hafer v.
Melo, 502 U.S. 21, 25 (1991) (“[O]fficial-capacity suits ‘generally represent only another way of

pleading an action against an entity of which an officer is an agent.’ Suits against state officials
in their official capacity therefore should be treated as suits against the State.”) (citation omitted)
(quoting Kentucky v. Graham, 473 U.S. 159, 165-66 (1985)). Accordingly, the suit against
Governor Baker in his official capacity is, for the purposes of sovereign immunity, a suit for
damages against the Commonwealth of Massachusetts. See also Tyler v. Massachusetts, 981 F.
Supp. 2d 92, 95 (D. Mass. 2013) (“[A] plaintiff may not resort to the expedient of simply naming
a state official as a defendant as a means of circumventing the Eleventh Amendment.”).
“As a general matter, states are immune under the Eleventh Amendment from private suit
in the federal courts, absent their consent.” Wojcik v. Massachusetts State Lottery Comm'n, 300
F.3d 92, 99 (1st Cir. 2002) (internal quotations omitted); see also Seminole Tribe of Florida v.

Florida, 517 U.S. 44, 54 (1996); Kentucky v. Graham, 473 U.S. 159, 167 n.14 (1985) (unless a
State has “waived its Eleventh Amendment immunity or Congress has overridden it, . . . a State
cannot be sued directly in its own name regardless of the relief sought.”). The Eleventh
Amendment has two exceptions: “First, Congress may abrogate a State’s immunity by expressly
authorizing such a suit pursuant to a valid exercise of power. Second, a State may waive its
sovereign immunity by consenting to be sued in federal court.” Maysonet-Robles v. Cabrero,
323 F.3d 43, 49 (1st Cir. 2003) (internal citations omitted). Eleventh Amendment immunity is
jurisdictional in nature, and “absent waiver, neither a State nor its agencies acting under its
control may be subject to suit in federal court.” Puerto Rico Aqueduct & Sewer Auth. v. Metcalf
& Eddy, Inc., 506 U.S. 139, 144 (1993).
Neither of the exceptions to sovereign immunity apply here. First, there has been no
waiver of sovereign immunity by the Commonwealth. Waivers must be “express,” and there is
nothing, express or otherwise, resembling such a waiver here. Limar Shipping Ltd. v. United
States, 324 F.3d 1, 6 (1st Cir. 2003). Second, the MTCA, enacted in 1978, operates as a limited

waiver of Eleventh Amendment immunity. It provides that “[c]laims against the commonwealth,
except as otherwise expressly provided . . . may be enforced in the superior court.” Mass. Gen.
Laws ch. 258, § 12. Nevertheless, the Supreme Judicial Court has clearly stated that this
language does not constitute a waiver of the Commonwealth’s Eleventh Amendment immunity
to suit in federal court. Irwin v. Comm’r of Dept. of Youth Servs., 388 Mass. 810, 819-20 (1983).
Accordingly, Count Two—that is, the claim that Governor Baker is vicariously liable for
the negligence of his agents at EOHHS and at the Probate Court—will be dismissed.
2. Judge McMahon, Sudders, Tsai, MacLeod, and McHoul
The amended complaint alleges that Judge McMahon, Sudders, Tsai, MacLeod, and
McHoul committed certain “common law torts” that “jointly and severally injured Kupperstein,

and directly and proximately caused Kupperstein to suffer financial harm, damage to his
reputation, and intentional infliction of emotional distress.” (Am. Compl. ¶¶ 16-20, 260). In
addition, although not tied to enumerated counts, the amended complaint alleges that Sudders
and Tsai “were negligent in retaining the lawyers [involved in the proceedings],” (id. ¶ 191), and
that McHoul “tort[i]ously interfered with the Trust’s sale of the Property to []Boyle, a Buyer who
signed a [purchase and sale agreement] to acquire the property.” (Id. ¶ 257).
As noted, the only allegations in the amended complaint against Judge McMahon relate
to orders he issued, and judicial immunity protects him from civil liability for those orders.
Furthermore, as employees of EOHHS, and University of Massachusetts Medical School,
MacLeod, Sudders and Tsai are public employees immunized by the MTCA. See McNamara v.
Honeyman, 406 Mass. 43, 47 (1989) (reviewing Mass. Gen. Laws. ch. 75 and finding that “the
university is an agency of the Commonwealth and thus is a public employer.”). Under the
MTCA, individual public employees are immune from suits stemming from negligent conduct
committed within the scope of their office or employment. Mass. Gen. Laws ch. 258, § 2;

Wiesman v. Hill, 629 F. Supp. 2d 106, 113 (D. Mass. 2009) (citing Jackson v. Town of Milton, 41
Mass. App. Ct. 908 (1996)).
Kupperstein has not alleged that MacLeod, Sudders, or Tsai were not acting within the
scope of their employment. In addition, none of the factual allegations in the amended complaint
suggest that they intended to inflict emotional distress against him, which is the only intentional
tort alleged. Agis v. Howard Johnson Co., 371 Mass. 140, 144-45 (1976) (noting that to state
such a claim, a plaintiff must allege, among other things, “that the actor intended to inflict
emotional distress or that he knew or should have known that emotional distress was the likely
result of his conduct”). The allegations against Sudders and Tsai are for vicarious liability only

(aside from his conclusory allegation that they were negligent in retaining the lawyers who
prosecuted the actions in question, which is not actionable against them under the MTCA). As to
MacLeod, the amended complaint alleges that she knew that the Suffolk Superior Court
complaint was false when she verified it, but as noted, he is prevented from relitigating the issue
of the validity of the MassHealth lien (and thus, whether the complaint was false).
McHoul, on the other hand, is not protected by immunity or by the MTCA, and
Kupperstein alleges that he tortiously interfered with his contract or business relationship with
Boyle. On June 4, 2015, she apparently signed an agreement to purchase the property, but when
McHoul told her attorney that Sheedy’s title to the property was “no good,” she repudiated the
agreement. (Am. Compl. ¶¶ 85-87).
To state a claim for tortious interference with a contract or business relationship, a
plaintiff must allege: “(1) the existence of a contract or business relationship which
contemplated economic benefit; (2) the defendant[’s] knowledge of the contract or business
relationship; (3) the defendant[’s] intentional interference with the contract or business

relationship for an improper purpose or by improper means; and (4) damages.” Swansen Dev.
Corp. v. City of Taunton, 423 Mass. 390, 338 (1996).
Among other issues, the amended complaint fails to allege that McHoul interfered with
the contract for any “improper purpose.” Id. Kupperstein is prevented from relitigating the issue
of whether the transfer from Thibodeau to Sheedy was valid. Therefore, to the extent McHoul
told Boyle that title was “no good,” he was proved correct.16
Accordingly, the state-law tort claims against Judge McMahon, Sudders, Tsai, MacLeod,
and McHoul will be dismissed.
IV. Conclusion
For the foregoing reasons, defendants’ motions to dismiss are GRANTED and the action

is hereby DISMISSED.
So Ordered.

/s/ F. Dennis Saylor IV
F. Dennis Saylor IV
Dated: July 21, 2021 Chief Judge, United States District Court

16 McHoul may also be protected by the absolute litigation privilege. The Supreme Judicial Court has held
that “statements by a party, counsel or witness in the institution of, or during the course of, a judicial proceeding are
absolutely privileged provided such statements relate to that proceeding.” Sriberg v. Raymond, 370 Mass. 105, 108
(1976); see also Visnick v. Caufield, 73 Mass. App. Ct. 809, 812 (2009). “The privilege extends to circumstances
where the statements are made preliminary to a proposed or contemplated judicial proceeding as long as they bear
some relation to the proceeding,” and McHoul was already representing the estate at the time of the alleged
conversation with Boyle. Fisher v. Lint, 69 Mass. App. Ct. 360, 366 (2007) (emphasis added).

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Source: Frix Law Library, https://www.frixlaw.com/law-library/cases/10199624. Public record. Not legal advice.