Keating

UNITED STATES DISTRICT COURT

MIDDLE DISTRICT OF FLORIDA

FORT MYERS DIVISION

DOUGLAS P. KEATING, JR.,

Plaintiff,

v. Case No: 2:25-cv-00598-JES-KRH

SHERIFF KEVIN RAMBOSK, in

his official capacity,

DEPUTY CHRISTIAN TULBURE,

individually, DEPUTY

CHRISTOPHER KARAM,

individually, DEPUTY RYAN

WILLIAMS, individually,

DEPUTY AUSTIN ROBINSON,

individually, SERGEANT

PATRICK J. STUBBE,

individually, JOHN DOE 1

(BOOKING AREA DEPUTY),

individually, JOHN DOE 2

(BOOKING AREA DEPUTY),

individually, JOHN DOE

3(BOOKING AREA SUPERVISOR),

individually, JOHN DOE 4

(TRANSPORT/CONTROL DEPUTY),

individually, JOHN DOE 5

(INFIRMARY ESCORT DEPUTY),

individually, and ANY

ADDITIONAL INDIVIDUALS OR

ENTITIES LATER IDENTIFIED,

Defendants.

OPINION AND ORDER

This matter comes before the Court on review of Defendant

Sheriff Kevin Rambosk’s (“Sheriff Rambosk”) Motion to Dismiss

Plaintiff’s Third Amended Complaint (Doc. #42) filed on April 22,

2026. Plaintiff, Douglas Keating, Jr. (“Keating”), filed his

Response in Opposition (Doc. #46) on April 30, 2026. For the

reasons set forth below, Sheriff Rambosk’s motion is granted in

part and denied in part.

I.

From August 1 to August 2, 2025, Keating was detained at the

Collier County Jail. (Doc. #28, ¶ 18.) While detained, Keating

used the inmate phone and was ordered by Deputy Christian Tulbure

(“Deputy Tulbure”) to end the call. (Id. ¶ 19.) Rather than end

the call Keating objected, prompting Deputies Tulbure and

Christopher Karam (“Deputy Karam”) to strike Keating in the head

and upper body. (Id. ¶¶ 20-22.) As Deputies Tulbure and Karam

were hitting Keating, Deputies Ryan Williams (“Deputy Williams”)

and Austin Robinson (“Deputy Robinson”) restrained Keating, but

did not object to Deputies Tulbure’s or Karam’s use of force. (Id.

¶¶ 23, 26-28.)

Keating exhibited visible injuries, including head trauma,

chest pain, and other physical injuries. (Id. ¶ 29.) Deputies

Tulbure, Karam, Robinson, and Williams were all aware of these

visible injuries and were present, alongside Sergeant Patrick J.

Stubbe (“Sergeant Stubbe”), when Keating requested medical

attention. (Id. ¶ 30-31.) Sergeant Stubbe, however, failed to

obtain timely and adequate medical treatment. (Id. ¶ 32.)

Instead, Deputies Tulbure, Karam, Williams, and Robinson placed

Keating into a different holding cell with standing water. (Id.

¶¶ 34-37.)

After being released, Keating obtained medical treatment

costing $4,273. (Id. ¶ 33.) Keating now brings the instant action

against the deputies in their individual capacities and Sheriff

Rambosk in his official capacity.

II.

Under Federal Rule of Civil Procedure 8(a)(2), a complaint

must contain a “short and plain statement of the claim showing

that the pleader is entitled to relief.” Fed. R. Civ. P. 8(a)(2).

This obligation “requires more than labels and conclusions, and a

formulaic recitation of the elements of a cause of action will not

do.” Bell Atl. Corp. v. Twombly, 550 U.S. 544, 555 (2007)(citation

omitted). As the Eleventh Circuit has recently summarized:

When reviewing a motion to dismiss, we accept the

plaintiff's allegations as true and construe them in the

light most favorable to the plaintiff. To survive a

motion to dismiss, a complaint must contain sufficient

factual matter, accepted as true, to state a claim to

relief that is plausible on its face. A claim is facially

plausible if the plaintiff pleads factual content that

allows the court to draw the reasonable inference that

the defendant is liable for the misconduct alleged. This

plausibility standard is not akin to a probability

requirement, but it asks for more than a sheer

possibility that a defendant has acted unlawfully. When

making the determination of whether a complaint states

a plausible claim, we draw on our judicial experience

and common sense.

. . .

We use a two-step process to determine whether a

claim survives Rule 12(b)(6) scrutiny. At the outset, we

determine what must be pled for each cause of action. .

. . Then, we consider the well-pleaded factual

allegations ... to determine whether they plausibly

suggest an entitlement to relief.

Caterpillar Fin. Servs. Corp. v. Venequip Mach. Sales Corp., 147

F.4th 1341, 1346–47 (11th Cir. 2025)(citations and internal

punctuation omitted).

Pro se pleadings are held to a less stringent standard than

counseled pleadings and, therefore, are liberally construed.

Campbell v. Air Jam. Ltd., 760 F.3d 1165, 1168 (11th Cir. 2014).

Nevertheless, this liberal construction does not entitle a court

to serve as de facto counsel to a pro se party or rewrite deficient

pleadings. See id. at 1168-69. Pro se litigants, however, are

still required to conform to procedural rules. See Albra v. Advan,

Inc., 490 F.3d 826, 829 (11th Cir. 2007); Goldsboro v. Ivey, No.

25-11394, 2026 WL 507421, at *3 (11th Cir. Feb. 24, 2026).

III.

A. The Court Strikes the Paragraphs Rendering the Third

Amended Complaint a Shotgun Pleading

“Complaints that violate either Rule 8(a)(2) or Rule 10(b),

or both, are often disparagingly referred to as ‘shotgun

pleadings.’” Weiland v. Palm Beach Cnty. Sheriff’s Off., 792 F.3d

1313, 1320 (11th Cir. 2015). Of the four categories outlined in

Weiland, the most prominent shotgun pleading occurs where a party

incorporates preceding paragraphs from the previous counts,

thereby causing most of the counts (i.e., all but the first) to

contain irrelevant factual allegations and legal conclusions. Id.

at 1324 (citations omitted).

Counts II through V “reallege[] and incorporate[] all

preceding paragraphs as if fully set forth herein.” (Doc. #28, ¶¶

67, 72, 76, 81.) By doing so, the Third Amended Complaint is a

“quintessential ‘shotgun’ pleading — the sort of pleading we have

been roundly condemning for 30 years.” See Keith v. DeKalb Cnty.,

749 F.3d 1034, 1045 n.39 (11th Cir. 2013)(collecting cases). As

a result, each count is now “replete with factual allegations that

could not possibly be material to that count, and that any

allegations that are material are buried beneath innumerable pages

of rambling irrelevancies.” Magluta v. Samples, 256 F.3d 1282,

1284 (11th Cir. 2001).

To Keating’s credit, the Third Amended Complaint is not so

long — nor so filled with factual allegations — to make it nearly

impossible to parse through the facts. However, this aspect of

the Third Amended Complaint must be addressed. Rather than dismiss

the Third Amended Complaint as a shotgun pleading, the Court will

instead strike the paragraphs that render it a shotgun pleading,

i.e., Doc. #28, ¶¶ 67, 72, 76, 81.

B. Keating Fails to Allege Sufficient Facts Establishing a

Policy or Custom

Keating claims Sheriff Rambosk in his official capacity is

liable because the policies and customs of the Collier County

Sheriff’s Office caused various constitutional violations. (Doc.

#28, ¶¶ 81-83.) Sheriff Rambosk argues Count V should be dismissed

because Keating fails to allege either a policy or a custom that

caused any alleged constitutional violation. (Doc. #42, pp. 4-

7.) Keating contends he sufficiently pled facts that create a

reasonable inference to support any of his underlying theories.

(Doc. #46, pp. 2-3.) The Court agrees with Sheriff Rambosk that

Keating failed to allege sufficient facts establishing a policy or

custom under either Keating’s failure to train or supervise theory

or ratification of the constitutional violations theory.

A municipality cannot be held vicariously liable for the

constitutional violations of its employee. See Monell v. Dep’t of

Soc. Servs., 436 U.S. 658, 691 (1978). The government as an entity

may be responsible, however, “when execution of a government’s

policy or custom, whether made by its lawmakers or by those whose

edicts or acts may fairly be said to represent official policy,

inflicts the injury.” See id. at 694. To impose such liability,

a plaintiff must show that: (1) “his constitutional rights were

violated;” (2) “the municipality had a custom or policy that

constituted deliberate indifference to that constitutional right;”

and (3) “the policy or custom caused the violation.” See Underwood

v. City of Bessemer, 11 F.4th 1317, 1333 (11th Cir. 2021)(quoting

McDowell v. Brown, 392 F.3d 1283, 1289 (11th Cir. 2004)).

Liability may be based on an official policy or “a practice

or custom that is so pervasive, as to be the functional equivalent

of a policy adopted by the final policymaker.” Khoury v. Miami-

Dade Cnty. Sch. Bd., 4 F.4th 1118, 1131 (11th Cir. 2021)(quoting

Church v. City of Huntsville, 30 F.3d 1332, 1342-43 (11th Cir.

1994)). “[A] policy is a decision that is officially adopted by

the municipality or created by an official of such rank that he or

she could be said to be acting on behalf of the municipality,”

while a “custom is an unwritten practice that is applied

consistently enough to have the same effect as a policy with the

force of law.” See Goebert v. Lee Cnty., 510 F.3d 1312, 1332 (11th

Cir. 2007)(citations omitted).

(1) Failure to Train and Supervise Deputies

When a plaintiff alleges a failure to train or supervise they

must allege facts showing the failure “evidences a deliberate

indifference” to the municipality’s inhabitants’ rights. See

Lewis v. City of W. Palm Beach, 561 F.3d 1288, 1293 (11th Cir.

2009)(citation omitted); Gold v. City of Miami, 151 F.3d 1346,

1350 (11th Cir. 1998)(applying same analysis to failure to

supervise claims). There must be “some evidence that the

municipality knew of a need to train and/or supervise in a

particular area and the municipality made a deliberate choice not

to take any action.” Lewis, 561 F.3d at 1293 (citation omitted).

A plaintiff can show this in two ways. First, there exists “[a]

pattern of similar constitutional violations by untrained

employees . . ..” See Connick v. Thompson, 563 U.S. 51, 62 (2011).

Second, even without prior events, the plaintiff can establish

deliberate indifference if “if the likelihood for constitutional

violation is so high that the need for training would be obvious.”

See Lewis, 561 F.3d at 1293. Keating only relies upon the first

premise.

Keating presents two conclusory allegations to support his

Monell claim. First, Keating claims “the constitutional violation

suffered by Plaintiff were caused by policies, customs, or

practices of the Sheriff’s Office.” (Doc. #28, ¶ 55.) Second,

Keating alleges “similar incidents involving excessive force and

punitive conditions occurred prior to Plaintiff’s incident and

were known to supervisory personnel.” (Id. ¶ 57.) These

allegations fail to provide the who, what, when, or where of

previous similar constitutional violations by untrained or

unsupervised employees and therefore are insufficient to support

a failure to train or supervise theory of liability. See Twombly,

544 U.S. at 555 (holding that conclusory allegations are

insufficient to plausibly state a claim). Without such

allegations, Keating is only left with his own single-incident,

1

which fails to plausibly state a policy or custom. See Craig v.

Floyd Cnty., 643 F.3d 1306, 1310 (11th Cir. 2011)(quoting City of

Okla. City v. Tuttle, 471 U.S. 808, 823-24 (1985)).

(2) Failure to Discipline Deputies

Where a plaintiff alleges a failure to take disciplinary

action against officers, it can be used to establish a custom if

the facts support a finding that “a persistent failure to take

disciplinary action against officers” resulted in the municipality

ratifying the conduct. See Fundiller v. City of Cooper City, 777

F.2d 1436, 1442-43 (11th Cir. 1985); Ingram v. Kubik, 30 F.4th

1241, 1256 (11th Cir. 2022)(quoting Fundiller, 777 F.2d at 1443)).

Where there are sufficient facts showing this persistent failure,

it also “provide[s] the causal link between the challenged conduct

1 Keating argues his allegations are not a “single incident,” but rather

a “multi-stage sequence of constitutional violations involving multiple

officers, multiple decision points, supervisory awareness, post-incident

review, and continued non-corrective institutional inaction.” (Doc.

#46, p. 2.) Though correct that he alleges multiple constitutional

violations over his day-long detention, Keating’s argument misses the

point. To support the Monell claim, Keating must show similar incidents

involving other detainees, since the violations at issue in this case

constitute a single incident, which generally cannot establish a policy

or custom. See Craig, 643 F.3d 1306, 1311 (discussing how a single

constitutional violation involving several employees is insufficient to

prove a policy or custom).

and the policy, because [the officer] would have been acting in

accordance with the policy of allowing or encouraging [violating

constitutional rights].” See Ingram, 30 F.4th at 1256 (quoting

Fundiller, 777 F.2d at 1443). Just as Keating’s failure to train

or supervise theory fails, so too does his failure to discipline

theory.

Keating’s only allegations relating to previous actions are:

(1) “similar incidents involving excessive force and punitive

conditions occurred prior to Plaintiff’s incident and were known

to supervisory personnel[;]” and (2) “[t]he Sheriff’s Office had

notice of these practices and failed to take corrective action. .

.. ” (Doc. #28, ¶¶ 57, 59.) These allegations are conclusory,

failing to provide the who, what, when, or where of the prior

incidents. See Twombly, 544 U.S. at 555 (holding that conclusory

allegations are insufficient to plausibly state a claim). This

again leaves Keating with his own incident, which is insufficient

to show a widespread custom or policy that allows or encourages

deputies to violate constitutional rights. See Craig, 643 F.3d at

1310. Accordingly, Keating fails to allege sufficient facts to

plausibly show a persistent failure to take disciplinary action

against officers.

C. The Fictitious Parties Will Not Be Dismissed at this

Time

Finally, Sheriff Rambosk argues the fictitious parties should

be dismissed because Keating has failed to describe the defendants

with sufficient specificity. (Doc. #42, p. 7.) Keating contends

dismissal of the fictitious parties is premature since “the

identities of involved officers remain uniquely within Defendants’

control and are reasonably expected to be identified through

discovery.” The Court agrees with Keating at this time.

Generally, “fictitious-party pleading is not permitted in

federal court.” See Richardson v. Johnson, 598 F.3d 734, 738 (11th

Cir. 2010)(citing New v. Sports & Recreation, Inc., 114 F.3d 1092,

1094 n.1 (11th Cir. 1997)). A limited exception applies “when the

plaintiff’s description of the defendant is so specific as to be

‘at the very worst, surplusage.’” See id. (quoting Dean v. Barber,

951 F.2d 1210, 1215-16 (11th Cir. 1992)).

Here, the Court finds it premature to dismiss the fictitious

parties. Keating identifies two individuals as “Booking Area

Deput[ies]” and three other individuals as “Booking Area

Supervisor,” “Transport/Control Deputy,” and “Infirmary Escort

Deputy.” This is sufficient for purposes of the instant motion.

Through the discovery process, Keating will have the ability to

obtain the identities of the deputies.? Accordingly, the motion

to dismiss the fictitious parties will be denied without prejudice.

For the reasons set forth in this order, the motion to dismiss

will be granted in part and denied in part.

Accordingly, it is now

ORDERED :

(1) Paragraphs 67, 72, 76, and 81 are STRUCK from the Third

Amended Complaint.

(2) Defendant Sheriff Kevin Rambosk’s (“Sheriff Rambosk”)

Motion to Dismiss Plaintiff’s Third Amended Complaint

(Doc. #42) is GRANTED IN PART AND DENIED IN PART. Count

V is DISMISSED without prejudice. The motion to dismiss

the fictitious-parties is DENIED without prejudice.

(3) The Clerk shall withhold judgment until the conclusion

of the case.

DONE AND ORDERED at Fort Myers, Florida, this 16th day of

June 2026.

4 pol

E. STEELE

SHNIOR UNITED STATES DISTRICT JUDGE

Copies: Parties of record

* The Court notes that should this occur, Keating must seek leave to file

an amended complaint, either from opposing parties or the Court, as he

will not be able to amend as of right. See Fed. R. Civ. P. 15(a) (2).