Santana v. City of Boston et al

UNITED STATES DISTRICT COURT
DISTRICT OF MASSACHUSETTS
)
DANIEL SANTANA, 	)
)
Plaintiff, 	)
)
v. 	)
)
CITY OF BOSTON, GUSTAVO 	) 	No. 1:25-cv-10334-JEK
MEDINA, ERIC FRANCIS, JOHN 	)
CANTY, EDWARD GATELY, SERGIO 	)
MEDRANO, RYAN FULLAM, and 	)
CHRISTOPHER KEATON, 	)
)
Defendants. 	)
)
MEMORANDUM AND ORDER ON DEFENDANTS’ MOTIONS TO DISMISS
KOBICK, J.
This civil rights action arises out of the August 2021 arrest of plaintiff Daniel Santana, who
the police identified as a suspect in response to a report of an individual firing a gun into the air in
downtown Boston. During the arrest, the responding officers broke the humerus bone in Santana’s
left arm. Santana was later charged with various firearms-related criminal offenses and detained.
The charges were eventually nolle prossed by the Commonwealth. Santana now brings claims of
false arrest, malicious prosecution, excessive force, and negligence against the City of Boston and
seven of its police officers, Officers Gustavo Medina, Eric Francis, John Canty, Edward Gately,
Sergio Medrano, Ryan Fullam, and Christopher Keaton. The City and the Officers have separately
moved to dismiss those claims. For the reasons that follow, the Court will grant the motions as to
Santana’s false arrest and malicious prosecution claims, but deny the motions as to his excessive
force claim and his claims of negligence against the City of Boston.
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BACKGROUND
The following facts, which are assumed true on a motion to dismiss, are drawn from the
second amended complaint, documents fairly incorporated by reference in that pleading, and
documents subject to judicial notice. See Bazinet v. Beth Israel Lahey Health, Inc., 113 F.4th 9, 15
(1st Cir. 2024).1 Those documents include Santana’s arrest report, records of his criminal
proceedings, and bodycam footage from the arresting officers. See ECF 14-1 through 14-6; ECF
24-2, ¶¶ 17, 35, 37 (second amended complaint referencing the arrest report and bodycam footage);
Esco v. City of Chicago, 107 F.4th 673, 678 (7th Cir. 2024) (district courts “may examine exhibits,
including video exhibits, . . . referenced in the pleading if they are central to the claim”); Watterson
v. Page, 987 F.2d 1, 3 (1st Cir. 1993) (on a motion to dismiss, a court can consider “documents the
authenticity of which are not disputed by the parties,” “official public records,” “documents central
to plaintiffs’ claim,” and “documents sufficiently referred to in the complaint”).
On August 16, 2021, Officers Medina and Francis received a call from the police dispatcher
that shots had been fired near Boston Medical Center. ECF 24-2, ¶ 15. According to a witness, the
dispatcher reported, an unidentified male on Albany Street had fired shots into the air after an
argument with another person. Id. ¶ 16; ECF 14-1, at 3. The witness had “observed a bright flash
of light, which he believed to be a muzzle-flash, and heard a loud blast that he perceived to be a
gunshot.” ECF 14-1, at 3. The suspect was described as a Black Non-Hispanic male wearing a
1 In opposing the motions to dismiss, Santana also moved for leave to file a second amended
complaint. See ECF 24, at 5-6. Before and at the hearing, the defendants indicated that they do not
oppose that motion and that the arguments made in support of their motions to dismiss the first
amended complaint would apply equally to the second amended complaint. See ECF 26.
Accordingly, with the parties’ agreement, the plaintiffs’ motion for leave to file a second amended
complaint is granted. The Court regards the second amended complaint, see ECF 24-2, as the
operative pleading, and the defendants’ motions to dismiss as seeking dismissal of that pleading.
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white T-shirt, blue jeans, white and blue Air Jordan sneakers, and a black fanny pack. ECF 24-2,
¶ 17; ECF 14-1, at 3.
Medina and Francis drove to Albany Street, where Medina identified Santana, a light-
skinned Hispanic male who was wearing the same clothes described by the dispatcher and a black
fanny pack. ECF 24-2, ¶¶ 18-19; ECF 14-1, at 3. Medina and Francis cornered Santana, exited
their vehicle with their weapons drawn, and instructed Santana to put his hands up. ECF 24-2,
¶¶ 20-21. Santana attempted to comply, but, as he explained to the officers, he was able to lift only
his right arm above his head because of an injury to his left shoulder that had required surgery two
months prior. Id. ¶¶ 23-25. Medina and Francis ordered Santana to get on the ground. Id. ¶ 26.
When Santana complied and laid on his back, the officers forcibly rolled him onto his stomach. Id.
¶¶ 26, 30. At some point during the interaction, Officers Canty, Gately, Medrano, Fullam, and
Keaton arrived on the scene. Id. ¶ 31.
Throughout the interaction, Santana was unarmed and complied with the orders given to
him. Id. ¶¶ 28-29. Despite his multiple pleas that, because of his left shoulder injury, he could not
bend his left arm, the officers forcibly twisted that arm and knelt on him. Id. ¶¶ 27, 30, 32. Santana
yelled, “[p]lease! I have a broken arm! I’m sorry! My arm is broken! Look! It’s broken! My
shoulder is broken! My left shoulder is broken, look! Please look! Please! My left shoulder please!
Please look man! My left shoulder.” Id. ¶ 33. Nevertheless, the officers continued to kneel on top
of him and wrench his arm behind his back, causing the humerus bone in his left arm to loudly
crack. Id. ¶¶ 34-35. Repeatedly, Santana screamed, “[y]ou’re breaking my arm!” and one of the
officers can be heard on bodycam footage saying, “the left arm is definitely fucking broken.” Id.
¶¶ 36-37. Santana was then transported to Boston Medical Center, where he was diagnosed with a
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mid-shaft fracture of his left humerus. Id. ¶ 38. As a result of the injury, Santana has limited use of
his left arm and suffers from permanent nerve damage. Id. ¶ 39.
After his arrest, Santana was charged in Boston Municipal Court with, among other things,
carrying a loaded firearm without a license and carrying ammunition without a firearm
identification (“FID”) card. Id. ¶ 40; ECF 14-2. According to the arrest report, after Officers
Medina and Francis had identified Santana as the suspect and ordered him to stop, Santana, who
was wearing the black fanny pack, continued walking away from them, ECF 14-1, at 3. They saw
Santana attempt to conceal himself behind a black Mercedes-Benz. Id. When he emerged from
behind the car, he was no longer carrying the fanny pack. Id. Officer Gately, who had an
unobstructed view of Santana, saw him drop the fanny pack near the car and, as it struck the
ground, heard a loud metallic thud that sounded to him like a firearm hitting the pavement. Id.
Officer Gately recovered the fanny pack and, upon searching it, found a black handgun with an
obliterated serial number loaded with 9mm rounds. Id. He also found a spent shell casing in the
fanny pack. Id.
The charges against Santana were dismissed by the Boston Municipal Court after he was
indicted by a grand jury in Suffolk Superior Court on charges of carrying a firearm without a
license, in violation of M.G.L. c. 269, § 10(a); possessing ammunition without an FID card, in
violation of M.G.L. c. 269, § 10(h)(1); and carrying a loaded firearm without a license, in violation
of M.G.L. c. 269, § 10(n). See ECF 24-2, ¶ 41; ECF 14-3; Commonwealth v. Santana, No.
2101CR002426 (Boston Municipal Ct.) (docket entries dated April 5, 2022); Commonwealth v.
Santana, No. 2284CR00100 (Mass. Super. Ct.), Dkt. No. 1. The Commonwealth later entered a
nolle prosequi on all three charges after the Superior Court granted Santana’s motion to suppress.
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Commonwealth v. Santana, No. 2284CR00100 (Mass. Super. Ct.), Dkt. Nos. 15, 24. In the wake
of his arrest, Santana was incarcerated for several months. ECF 24-2, ¶ 40.
On August 15, 2024, Santana initiated this lawsuit in Suffolk Superior Court. ECF 1-3, at
3. He filed an amended complaint on February 23, 2025. Id. at 5-17. That pleading asserted claims
against the City of Boston and Officers Medina, Francis, Gately, Canty, Medrano, Fullam, and
Keaton, in their individual capacities. ECF 24-2, ¶¶ 4-7. Against all defendants, Santana alleged
claims of negligence (Count I) and, under 42 U.S.C. § 1983, claims of false arrest, malicious
prosecution, and excessive force in violation of the Fourth Amendment (Counts III, IV, and V,
respectively). Id. ¶¶ 55-60, 69-94. Against only the City of Boston, he also alleged negligent hiring,
training, retention, or supervision (Count II). Id. ¶¶ 61-68.
The defendants removed the case to this Court in February 2025. ECF 1. Santana was
granted leave to file a second amended complaint, which asserts the same claims against the same
defendants. See supra note 1; ECF 24-2, ¶¶ 55-94. In two separate motions, the City of Boston and
the individual police officer defendants moved to dismiss that pleading for failure to state a claim
pursuant to Federal Rule of Civil Procedure 12(b)(6). ECF 10, 13. After the Court held a hearing
on those motions, Santana consented to the dismissal of the excessive force claim against Officers
Canty and Medrano without prejudice. ECF 33, at 1; ECF 31.
STANDARD OF REVIEW
In evaluating a motion to dismiss under Federal Rule of Civil Procedure 12(b)(6), the Court
must determine “whether, construing the well-pleaded facts of the complaint in the light most
favorable to the plaintif[f], the complaint states a claim for which relief can be granted.” Cortés-
Ramos v. Martin-Morales, 956 F.3d 36, 41 (1st Cir. 2020) (quotation marks omitted). The
complaint must allege “a plausible entitlement to relief.” Bell Atl. Corp. v. Twombly, 550 U.S. 544,
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559 (2007). “A claim has facial plausibility when the plaintiff pleads factual content that allows
the court to draw the reasonable inference that the defendant is liable for the misconduct alleged.”
Ashcroft v. Iqbal, 556 U.S. 662, 678 (2009). “While legal conclusions can provide the framework
of a complaint, they must be supported by factual allegations.” Id. at 679.
DISCUSSION
I. 	Claims Against the Individual Defendants.
The Court first addresses the individual police officer defendants’ motion to dismiss Counts
III, IV, and V, which assert Fourth Amendment claims under 42 U.S.C. § 1983, and Count I, which
asserts a negligence claim under Massachusetts common law.
A. 	Malicious Prosecution Claim.
Count IV asserts that the individual defendants instituted criminal proceedings against
Santana without probable cause, in violation of his right to be free from malicious prosecution
under the Fourth Amendment. A Fourth Amendment claim for malicious prosecution protects
individuals “targeted for unreasonable, baseless prosecutions, and who, as a result, are detained
without probable cause during the pretrial period.” Hernandez-Cuevas v. Taylor, 723 F.3d 91, 98
(1st Cir. 2013). To make out such a claim, a plaintiff must plausibly allege that “the defendant
(1) caused (2) a seizure of the plaintiff pursuant to legal process unsupported by probable cause,
and (3) criminal proceedings terminated in plaintiff’s favor.” Id. at 101 (quotation marks omitted).
The individual defendants contend that Santana’s malicious prosecution claim falters at the second
element, because the fact that he was indicted by a grand jury establishes that there existed
probable cause to initiate criminal proceedings against him.
The Court agrees. “Generally, a grand jury indictment definitively establishes probable
cause” to bring charges. Gonzalez Rucci v. I.N.S., 405 F.3d 45, 49 (1st Cir. 2005); accord Kennedy
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v. Town of Billerica, 617 F.3d 520, 534 (1st Cir. 2010). An exception to this rule exists, however,
if the plaintiff plausibly alleges that “law enforcement defendants wrongfully obtained the
indictment by knowingly presenting false testimony to the grand jury.” Gonzalez Rucci, 405 F.3d
at 49. Santana does not dispute that a grand jury indicted him on multiple charges arising out of
the arrest at issue in this case, including charges of carrying a firearm without a license, possessing
ammunition without an FID card, and carrying a loaded firearm without a license. See ECF 14-3.
And Santana does not allege that the defendants wrongfully obtained that indictment through false
or misleading testimony presented to the grand jury. Consequently, the grand jury’s indictment
forecloses Santana’s claim that he was detained on charges that were not supported by probable
cause, and his malicious prosecution claim against the individual officers must be dismissed. See
Kennedy, 617 F.3d at 534 (affirming district court’s dismissal of malicious prosecution claim
“since a grand jury found there was probable cause to arrest” the plaintiffs, whose efforts to
“impugn the grand jury testimony” were untimely); Díaz-Nieves v. United States, 858 F.3d 678,
688 (1st Cir. 2017) (same).
B. 	False Arrest Claim.
Count III asserts a false arrest claim under the Fourth Amendment, which protects against
“unreasonable . . . seizures” of the person. U.S. C ONST. amend. IV. To state a false arrest claim,
Santana must plausibly allege that the arresting officers lacked probable cause to believe that he
had committed or was committing a crime. See Jordan v. Town of Waldoboro, 943 F.3d 532, 545
(1st Cir. 2019), abrogated on other grounds by Thompson v. Clark, 596 U.S. 36 (2022). Probable
cause for a warrantless arrest exists “when, at the time of the arrest, the ‘facts and circumstances
within the officer’s knowledge . . . are sufficient to warrant a prudent person, or one of reasonable
caution, in believing, in the circumstances shown, that the suspect has committed, is committing,
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or is about to commit an offense.’” Holder v. Town of Sandown, 585 F.3d 500, 504 (1st Cir. 2009)
(quoting Michigan v. DeFillippo, 443 U.S. 31, 37 (1979)). “To determine whether an officer had
probable cause for an arrest, ‘[courts] examine the events leading up to the arrest, and then decide
whether these historical facts, viewed from the standpoint of an objectively reasonable police
officer, amount to probable cause.’” District of Columbia v. Wesby, 583 U.S. 48, 56-57 (2018)
(quoting Maryland v. Pringle, 540 U.S. 366, 371 (2003)).
In seeking dismissal of Santana’s false arrest claim, the individual officers make two
arguments: (1) that the grand jury indictment establishes that the arrest was supported by probable
cause, and (2) that, in any event, the undisputed facts and circumstances known to the arresting
officers demonstrate that they had probable cause to arrest Santana. As to the first argument, the
First Circuit has held that when a grand jury has found probable cause through its issuance of an
indictment, that finding “dispos[es] of false arrest, malicious prosecution, and other derivative
claims.” Kennedy, 617 F.3d at 534. That holding appears to foreclose Santana’s assertion that his
arrest was not supported by probable cause and, as with his malicious prosecution claim, requires
dismissal of the false arrest claim.2
But even if the grand jury’s later indictment did not definitively establish that probable
cause existed at the time of the arrest, Santana’s false arrest claim must nevertheless be dismissed.
Drawing all factual inferences in his favor, the allegations in the second amended complaint,
together with the facts contained in the documents incorporated by reference, establish that the
individual officers had probable cause to arrest Santana. Officers Medina and Francis learned,
2 The analysis in Kennedy does not distinguish between probable cause to arrest and probable
cause to initiate criminal proceedings. See, e.g., Kee v. City of New York, 12 F.4th 150, 166 (2d Cir.
2021) (discussing the difference); Sykes v. Anderson, 625 F.3d 294, 310-11 (6th Cir. 2010) (same);
Jenkins v. Chief Just. of Dist. Ct. Dep’t, 416 Mass. 221, 245 (1993) (noting the difference between
“probable cause to arrest [or search] and probable cause to bind over” (quotation marks omitted)).
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through the police dispatcher, that a witness had observed a Black Non-Hispanic male, in a white
T-shirt, blue jeans, and blue and white Air Jordans, and with a black fanny pack shoot a gun into
the air after an argument. Medina and Francis found Santana—an individual who matched the
description of the suspect precisely, with the exception of the description of his skin color—shortly
thereafter in the vicinity of the shooting. Officer Gately watched Santana attempt to conceal
himself behind a car and then drop the fanny pack, causing a metallic thud that, to Gately’s ears,
sounded like a firearm hitting the ground. Santana then emerged from behind the car without the
fanny pack. These facts, known to the arresting officers,3 would warrant a reasonably prudent
officer in believing that Santana was the person who had reportedly committed a criminal offense
by shooting a gun in the air near the Boston Medical Center, and then arresting him for, among
other things, carrying a loaded firearm without a license. See Holder, 585 F.3d at 504; Acosta v.
Ames Dep’t Stores, Inc., 386 F.3d 5, 10 (1st Cir. 2004) (“The uncorroborated testimony of a victim
or other percipient witness, standing alone, ordinarily can support a finding of probable cause.”).
Santana has two principal rejoinders. First, Santana contends that the witness reported
seeing a Black Non-Hispanic male shoot the gun, but he is a light-skinned Hispanic male. This
single discrepancy between the description of the suspect and Santana does not, given the other
circumstances known to the arresting officers, defeat probable cause. See Abreu-Guzman v. Ford,
241 F.3d 69, 74 (1st Cir. 2001) (when “a physical description closely resembles an individual,
some discrepancies in the description do not undermine the reasonableness of officers’ belief that
an arrestee was the person” identified); Lallemand v. Univ. of Rhode Island, 9 F.3d 214, 217 (1st
3 The First Circuit has long recognized the rule that “law enforcement officials cooperating in
an investigation are entitled to rely upon each other’s knowledge of facts when forming the
conclusion that a suspect has committed or is committing a crime.” United States v. Meade, 110
F.3d 190, 193 (1st Cir. 1997).
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Cir. 1993) (probable cause existed even though there were several discrepancies between the
description of the suspect’s appearance and his actual appearance). Santana’s appearance—his
white T-shirt, blue jeans, blue and white Air Jordan sneakers, and black fanny pack—otherwise
matched the description of the suspect exactly. And Officer Gately heard him drop what sounded
like a gun when Santana dropped the fanny pack in an apparent effort to conceal it.
Second, Santana contends that because the Superior Court granted his motion to suppress,
the officers necessarily lacked probable cause to arrest him. But Santana has not supplied the Court
with the Superior Court’s decision on his motion to suppress and that decision is not accessible on
the Superior Court’s docket. Absent any basis for discerning the Superior Court’s reasoning, the
fact that Santana’s motion to suppress was granted in Superior Court does not undercut the
conclusion that Santana has not plausibly alleged facts in this Court that negate probable cause.4
Accordingly, his Fourth Amendment false arrest claim must be dismissed.
C. 	Excessive Force Claim.
Count V asserts that the individual defendants used excessive force during Santana’s arrest,
in violation of the Fourth Amendment, when they pointed a gun at him and twisted his left arm
while kneeling on his back, resulting in a fractured left humerus. Santana has consented to
dismissal of his excessive force claim without prejudice as to Officers Canty and Medrano, but not
as to the remaining defendants, who raise several arguments. Officer Gately claims that because
4 Santana does allege in the second amended complaint that the charges pending against him
in the Boston Municipal Court were dismissed with prejudice “for lack of probable cause of the
stop and arrest.” ECF 24-2, ¶ 41. That allegation is directly contradicted by the docket of the
Boston Municipal Court, which shows that the charges against Santana in that Court were
dismissed because he had been indicted by a grand jury in the Superior Court. See Commonwealth
v. Santana, No. 2101CR002426 (Boston Municipal Ct.) (docket entries dated April 5, 2022);
Henning v. Wachovia Mortg., FSB, 969 F. Supp. 2d 135, 147 (D. Mass. 2013) (“When [public]
documents contradict allegations in the complaint, the documents trump the allegations.”).
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he did not physically interact with Santana during the arrest, he cannot be held liable for the use
of excessive force. Officers Medina, Francis, Gately, Fullam, and Keaton also argue that the force
used was objectively reasonable and that they are entitled to qualified immunity.
For Section 1983 claims, “liability in damages can only be imposed upon officials who
were involved personally in the deprivation of constitutional rights.” Pinto v. Nettleship, 737 F.2d
130, 132 (1st Cir. 1984); accord Cepero-Rivera v. Fagundo, 414 F.3d 124, 129 (1st Cir. 2005).
Gately contends that the excessive force claim against him must be dismissed because his bodycam
footage shows that he was not personally involved in Santana’s arrest. That footage captures Gately
exiting his patrol car, drawing his firearm, pointing it at Santana, and ordering Santana to “get on
the ground.” ECF 14, Ex. E, at 00:15-00:40. At a minimum, it shows that Gately was not a mere
spectator during Santana’s arrest; he pointed a gun directly at Santana. The footage refutes Gately’s
argument that he cannot be liable because he was not personally involved in Santana’s arrest, and
it shows that Gately may have contributed to excessive use of force or failed to intervene to protect
Santana from excessive use of force. See Stamps v. Town of Framingham, 813 F.3d 27, 39-41 (1st
Cir. 2016) (pointing a gun at a prone, non-resistant individual who poses no threat can constitute
excessive force in violation of the Fourth Amendment). The excessive force claim against Gately
will not, accordingly, be dismissed for failure to plausibly allege personal involvement.
Officers Medina, Francis, Gately, Fullam, and Keaton next argue that they are entitled to
qualified immunity on the excessive force claim. Qualified immunity protects public officials
“from liability for civil damages insofar as their conduct does not violate clearly established
statutory or constitutional rights of which a reasonable person would have known.” Harlow v.
Fitzgerald, 457 U.S. 800, 818 (1982). “The qualified immunity inquiry proceeds with a now-
familiar two-part test: (1) whether the facts alleged or shown by the plaintiff make out a violation
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of a constitutional right; and (2) if so, whether the right was clearly established at the time of the
defendant’s alleged violation.” Penate v. Hanchett, 944 F.3d 358, 366 (1st Cir. 2019) (quotation
marks omitted); see Est. of Rahim by Rahim v. Doe, 51 F.4th 402, 410 (1st Cir. 2022) (“The prongs
need not be addressed in order, and an officer may be entitled to immunity based on either prong.”).
The Court will address each prong in turn.
The Fourth Amendment’s guarantee of the right against unreasonable seizure includes a
right against the use of excessive force “in the context o[f] arrest[s] and investigatory stop[s].”
Graham v. Connor, 490 U.S. 386, 394 (1989). To prevail on a claim of excessive force, “a plaintiff
must show that the defendant employed force that was unreasonable under all the circumstances.”
Morelli v. Webster, 552 F.3d 12, 23 (1st Cir. 2009). In determining whether an application of force
is reasonable, a Court must consider “‘the severity of the crime at issue, whether the suspect
pose[d] an immediate threat to the safety of the officers or others, and whether [the suspect was]
actively resisting arrest or attempting to evade arrest by flight.’” Gray v. Cummings, 917 F.3d 1, 8
(1st Cir. 2019) (quoting Graham, 490 U.S. at 396). The factors are analyzed objectively and
considered from “the perspective of a reasonable officer on the scene, rather than with the 20/20
vision of hindsight.” Graham, 490 U.S. at 396-97.
Applying these factors to the allegations in the second amended complaint, which at this
stage are assumed true, Santana has plausibly alleged a violation of his right against the use of
excessive force. While the crime reported by the police dispatcher—shooting a gun into the air
near a hospital and in the middle of an urban neighborhood—was serious, Santana complied with
Officer Francis and Medina’s instructions when they cornered him, exited their vehicle with their
weapons drawn, and instructed him to put his hands up. He complied with their order to lie on the
ground, and he complied with all subsequent orders. After the officers forcibly rolled him on his
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stomach, pinned him on the ground, and knelt on his back, he repeatedly warned them that he had
a left shoulder injury that prevented him from moving his left arm. Santana did not resist at any
point during the interaction, he was unarmed throughout the interaction, and he was not, when the
officers approached him, actively committing any criminal offense. Nevertheless, the officers
wrenched his left arm behind his back with such force that his left humerus fractured loudly,
leaving no doubt in the officers’ minds that they had broken his arm. These facts easily clear the
bar for plausibly alleging objectively unreasonable use of force.
The individual defendants may still be entitled to qualified immunity if the law applicable
to their use of force was not clearly established at the time of Santana’s arrest. The “clearly
established” prong involves two sub-inquiries. The first “‘focuses on the clarity of the law at the
time of the violation.’” Penate, 944 F.3d at 366 (quoting Drumgold v. Callahan, 707 F.3d 28, 42
(1st Cir. 2013)). The second “‘focuses more concretely on the facts of the particular case and
whether a reasonable defendant would have known that his conduct violated the plaintiff’s
constitutional rights.’” Id. (quoting Drumgold, 707 F.3d at 42). “The salient question is whether
the state of the law at the time of the alleged violation gave the defendant fair warning that his
particular conduct was unconstitutional.” Maldonado v. Fontanes, 568 F.3d 263, 269 (1st Cir.
2009).
The law at the time of Santana’s arrest clearly established that kneeling on a non-resisting,
prone arrestee’s back and wrenching his arm with such force as to break his arm is unconstitutional.
The First Circuit explained in 2009 that its case law “supplies a crystal clear articulation of the
right, grounded in the Fourth Amendment, to be free from the use of excessive force by an arresting
officer.” Morelli, 552 F.3d at 23. And on Santana’s well-pled version of the facts, an objectively
reasonable officer would have known that his conduct violated Santana’s Fourth Amendment
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rights. The officers may have reasonably believed that Santana was armed when they first
encountered him, as they were responding to a report of a shooting. But they did not break his arm
until after they had surrounded him, ordered him to get down on the ground, secured him, watched
him comply with their orders, noticed that he made no effort to resist arrest, and heard him say
repeatedly that he could not use his left arm due to a prior injury. The facts of this case are
sufficiently analogous to prior First Circuit precedent to put a reasonable police officer on notice
that, under those circumstances, wrenching Santana’s injured arm with force enough to fracture it
was unconstitutional. See, e.g., Heredia v. Roscoe, 125 F.4th 34, 47-48 (1st Cir. 2025) (citing cases
and explaining that its precedent has been clear since 2010 that “it is unconstitutional for an officer
to use a takedown maneuver to take an arrestee to the ground, hitting the arrestee’s head on the
pavement, after the arrestee had already shown his hands and submitted to arrest”); Raiche v.
Pietroski, 623 F.3d 30, 39 (1st Cir. 2010) (holding that a “reasonable officer with training . . . would
not have needed prior case law on point to recognize that it is unconstitutional to tackle a person
who has already stopped in response to the officer’s command to stop and who presents no
indications of dangerousness”); Jennings v. Jones, 499 F.3d 2, 19 (1st Cir. 2007) (“[A]n objectively
reasonable officer . . . would not have believed that it was lawful to increase the amount of force
that he used after [plaintiff] ceased resisting and stated that [defendant] was hurting him.”).
Officers Medina, Francis, Gately, Fullam, and Keaton are not, accordingly, entitled to dismissal of
Santana’s excessive force claim on the basis of qualified immunity.
D. 	Negligence Claim.
Count I asserts a negligence claim, premised on the contention that the individual
defendants violated a duty of care “in the application of force when detaining [Santana] and taking
him in to custody.” ECF 24-2, ¶ 56. These defendants argue that the claim is barred by the
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Massachusetts Tort Claims Act (“MTCA”), which provides that the exclusive remedy for injuries
“caused by the negligent or wrongful act or omission of any public employee while acting within
the scope of his office or employment” shall be an action against the public employer. M.G.L.
c. 258, § 2. Public employers include “the commonwealth and any county, city, town, educational
collaborative, or district,” as well as “any department, office, commission, committee, council,
board, division, bureau, institution, agency or authority thereof.” Id. § 1. The MTCA thus “shields
public employees from personal liability for negligent conduct” performed in the scope of their
employment. Caisse v. DuBois, 346 F.3d 213, 218 (1st Cir. 2003) (citing McNamara v. Honeyman,
406 Mass. 43, 46 (1989)). Here, the individual defendants were employees of the Boston Police
Department acting within the scope of their responsibilities when they interacted with Santana.
Accordingly, Santana’s negligence claim may be asserted only against their employer; as to the
individual defendants, it must be dismissed as barred by the MTCA.
II. 	Claims Against the City of Boston.
The Court next addresses Santana’s claims against the City of Boston.
A. 	Municipal Liability Under Section 1983.
Counts III through V assert Fourth Amendment claims against the City under 42 U.S.C.
§ 1983. “[A] municipality can be found liable under § 1983 only where the municipality itself
causes the constitutional violation at issue” because “[r]espondeat superior or vicarious liability
will not attach under § 1983.” City of Canton v. Harris, 489 U.S. 378, 385 (1989) (citing Monell
v. Dep’t of Soc. Servs. of City of New York, 436 U.S. 658, 694-95 (1978)). A plaintiff must allege
that the municipality, “through its deliberate conduct, . . . was the ‘moving force’ behind the injury
alleged,” Bd. of Cnty. Comm’rs of Bryan Cnty., Oklahoma v. Brown, 520 U.S. 397, 404 (1997),
and that the illegal action was taken “pursuant to official municipal policy” or custom “of some
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nature,” Monell, 436 U.S. at 691. “Official municipal policy includes the decisions of a
government’s lawmakers, the acts of its policymaking officials, and practices so persistent and
widespread as to practically have the force of law.” Connick v. Thompson, 563 U.S. 51, 61 (2011).
It may also encompass a municipality’s failure to train its employees, if the plaintiff can
demonstrate that “municipal decisionmakers either knew or should have known that training was
inadequate but nonetheless exhibited deliberate indifference to the unconstitutional effect of those
inadequacies.” Wadsworth v. Nguyen, 129 F.4th 38, 68 (1st Cir. 2025) (quotation marks omitted).
“Deliberate indifference requires a showing that [the City] disregarded a known or obvious risk of
serious harm following from its failure to develop an adequate training program.” Id.
Santana claims that his injuries from the false arrest, malicious prosecution, and excessive
force occurred because of the individual officers’ execution of the City of Boston’s policies or
customs, which were the moving force behind the constitutional violations he has asserted.
Because Santana has failed to allege plausible claims for false arrest or malicious prosecution
against the individual defendants, those claims against the City of Boston must also be dismissed
for lack of an underlying constitutional violation. See Doe v. City of Boston, 145 F.4th 142, 156
(1st Cir. 2025) (“[T]o find that a city is subject to Monell liability, a court must first find that a city
employee committed an underlying constitutional violation.”). As to the excessive force claim,
Santana alleges he was subjected to excessive force during his arrest because (1) the Boston Police
Department maintained a custom under which officers understood that they should not report other
officers’ excessive force during arrests, ECF 24-2, ¶¶ 43-50; and (2) the Boston Police Department
failed to investigate and discipline officers for using excessive force, id. ¶¶ 42, 49-50.
Both of these theories support a plausible Monell claim against the City. As to the first,
Santana alleges that the City tolerated excessive force during arrests by upholding a “code of
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silence” or a “blue wall” under which officers knew they should not report misconduct by fellow
officers. Id. ¶ 43. “[U]nlike a ‘policy,’ which comes into existence because of the top-down
affirmative decision of a policymaker, a custom develops from the bottom-up.” Baron v. Suffolk
Cnty. Sheriff’s Dept., 402 F.3d 225, 236 (1st Cir. 2005), abrogated on other grounds by Jennings
v. Jones, 587 F.3d 430, 438 n.10 (1st Cir. 2009). A custom may be attributable to the municipality
when it is “so well settled and widespread that the policymaking officials of the municipality can
be said to have either actual or constructive knowledge of it yet did nothing to end the practice.”
Id. at 236-37. Santana’s allegations fit this pattern. He alleges that the Boston Police Department
had a custom of “making it difficult for citizens to file complaints about the conduct of Boston
police officers,” for complaints to be properly investigated, and for officers to be properly
disciplined for misconduct. ECF 24-2, ¶¶ 48-49. The custom allegedly prevented the Department
from “properly investigat[ing] claims and failing to discipline officers who used unreasonable
force.” Id. ¶¶ 43, 46, 48-49. Santana bolsters his assertions by alleging a series of events in the
1990s when officers were knowingly shielded from investigations for misconduct, including the
use 	of 	excessive 	force. 	Id. 	¶¶ 	44-45. 	And 	he 	quotes 	the 	former 	Mayor 	of 	Boston’s
acknowledgement that “officers were intimidated into silence for fear of retaliation” in internal
investigations. Id. ¶ 46. Viewed in the light most favorable to Santana, these allegations could
plausibly establish that the City’s custom of a “code of silence” or “blue wall” caused the excessive
force violation that Santana has asserted.
Santana’s second theory alleges that the Boston Police Department failed to train,
investigate, and discipline officers for using excessive force. In a failure to train claim, a plaintiff
must show that “municipal decisionmakers either knew or should have known that training was
inadequate but nonetheless exhibited deliberate indifference to the unconstitutional effects of those
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inadequacies.” Haley v. City of Boston, 657 F.3d 39, 52 (1st Cir. 2011). “A pattern of similar
constitutional violations” is “‘ordinarily necessary’ to demonstrate deliberate indifference.”
Connick, 563 U.S. at 62. The same standard applies where the claim is a failure to supervise or
discipline. See Rodriques v. Furtado, 950 F.2d 805, 813 (1st Cir. 1991) (citing Bordanaro v.
McLeod, 871 F.2d 1151, 1158 (1st Cir. 1989)). The First Circuit’s decision in Haley v. City of
Boston is instructive. The plaintiff there alleged that the unconstitutional suppression of evidence,
“if not the result of a standing policy, was precipitated by poor training, to which the City was
deliberately indifferent.” Haley, 657 F.3d at 52. The First Circuit held that the plaintiff sufficiently
stated a claim that the City “turned a blind eye to the need for training” in part because the Boston
Police Department’s “failure to disclose [witness] statements is wholly unexplained” and
“[d]isclosure abuses are a recurring problem in criminal cases.” Id. at 52-53. Likewise, Santana
alleges that the Department “failed to provide adequate training as to the appropriate ways in which
to take an individual into custody,” ECF 24-2, ¶ 65; “fail[ed] to properly investigate complaints of
misconduct” regarding excessive force, id. ¶¶ 42-47; and failed “to discipline officers who used
unreasonable or excessive force,” id. ¶ 42. While a “different kind of proof” is required for each
Monell claim, Santana can draw on “many of th[e] same facts” from his unconstitutional custom
claim, which support the inference that the City’s failure to investigate or discipline officers for
use of excessive force amounted to deliberate indifference. Haley, 657 F.3d at 51-52. Taken
together, Santana’s allegations permit the inference that the Boston Police Department failed to
adequately train, investigate, and discipline officers regarding excessive force during arrests, and
that these failures were the moving force behind the excessive force he allegedly experienced.
Santana has, accordingly, sufficiently stated a Section 1983 claim against the City based
on its alleged custom of perpetuating a “code of silence” and its purported failure to train,
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investigate, and discipline officers for their unwarranted use of force. The City’s motion to dismiss
Count V will be denied.
B. 	Negligence Claims Under the MTCA.
Counts I and II assert claims of negligence and negligent hiring, training, retention, or
supervision, respectively, against the City of Boston. The City contends that both claims are barred
because Santana failed to timely present them to the City in compliance with the MTCA, and that
Count II is insufficiently pleaded.
Under the MTCA, a plaintiff may not institute a civil action against a public employer
unless (1) he has “presented his claim in writing to the executive officer of such public employer
within two years after the date upon which the cause of action arose,” and (2) the executive officer
has denied the claim in writing or failed to issue a denial within six months. M.G.L. c. 258, § 4.
“Th[e] strict presentment requirement is a statutory prerequisite for recovery under the [MTCA].”
Shapiro v. City of Worcester, 464 Mass. 261, 267 (2013). Santana alleges that, before instituting
this action, he served the City of Boston with a notice of claim on August 15, 2023, within the two-
year limitations period provided by the MTCA. ECF 24-2, ¶ 12. The City disputes this allegation,
claiming that the City has no record of receiving such a letter in August 2023. ECF 11, at 7. In
response, Santana attached the presentment letter, dated August 15, 2023, ECF 24-1, at 1-4, and
submitted an affidavit certifying the delivery of the presentment letter within the deadline, ECF
32, at 1-2. But the Court need not look to these latter documents, because an affirmative defense,
such as the argument that a claim is barred by defective presentment, may prevail on a motion to
dismiss only if “‘the facts establishing the defense are clear on the face of the plaintiff’s
pleadings.’” Trans-Spec Truck Serv., Inc. v. Caterpillar Inc., 524 F.3d 315, 320 (1st Cir. 2008)
(brackets omitted) (quoting Blackstone Realty LLC v. F.D.I.C., 244 F.3d 193, 197 (1st Cir. 2001));
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see Theisz v. Mass. Bay Transp. Auth., 481 Mass. 1012, 1014 (2018) (inadequate presentment is
an affirmative defense). Where the Court must accept as true Santana’s allegation that he did timely
present his claims to the City, it cannot accept at this stage in the proceedings the City’s claim of
defective presentment or its argument that the MTCA requirements have not been met.
The City also argues that Santana failed to plead sufficient facts to support allegations that
it was negligent in hiring, training, retaining, and supervising the individual defendants.
Supervisory negligence can lie against municipalities “where the municipality knew or should
have known about an underlying, identifiable tort which was committed by named or unnamed
public employees.” Kennedy, 617 F.3d at 533. To establish supervisory negligence under
Massachusetts law, “a plaintiff must show that the ‘employer [became] aware or should have
become aware of problems with an employee that indicated his unfitness, and the employer fails
to take further action such as investigating, discharge or reassignment.’” Helfman v. Northeastern
Univ., 485 Mass. 308, 326 (2020). This notice requirement is applied to claims that employers
negligently trained, supervised, retained, and hired employees. Id.; see Doe v. Stonehill Coll., Inc.,
55 F.4th 302, 338 (1st Cir. 2022).
In light of the conclusion that the Monell claim alleged in Count V can proceed on a theory
of failure to train, investigate, or discipline, the Court finds that the same reasoning applies to
Santana’s negligent supervision, training, and hiring theory under state law. Weiss v. Lavallee, No.
01-cv-40177-FDS, 2005 WL 8176485, at *22 (D. Mass. Oct. 7, 2005) (“[T]he negligence required
for recovery under the MTCA for alleged inadequate police training is similar, if not identical, to
the deliberate indifference required under § 1983 in municipal liability claims.” (citing Parker v.
Town of Swansea, 270 F. Supp. 2d 92, 101-02 (D. Mass. 2003))). Santana’s negligent retention
theory similarly survives because this theory “fall[s] under the umbrella of negligent supervision.”
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Doe v. Brandeis Univ., 177 F. Supp. 3d 561, 613 (D. Mass. 2016) (“‘Negligent supervision’ is
probably a more accurate label for the tort of negligent retention, because in some situations the
appropriate course of action for an employer is to dismiss an employee and in other situations it
may be more appropriate to reassign that employee or take some other course of action.” (quoting
Great No. Ins. Co. v. Paino Assocs., 364 F. Supp. 2d 7, 20 (D. Mass. 2005))). And Santana has
specifically alleged that two of the defendants—Officers Gately and Medina—have had previous
complaints filed against them for use of force. ECF 24-2, ¶¶ 52-53. Accepting Santana’s allegations
as true and viewing them in the light most favorable to him, Santana plausibly alleges that the City
was negligent in its hiring, retention, training, or supervision of the individual defendants.
Accordingly, the City’s motion to dismiss Counts I and II will be denied.
CONCLUSIONS AND ORDERS
For the foregoing reasons, the defendants’ motions to dismiss, ECF 10, 13, are GRANTED
in part and DENIED in part. With respect to the City of Boston, Counts III and IV are DISMISSED
with prejudice, and Counts I, II, and V remain. With respect to Officers Medina, Francis, Gately,
Fullam, and Keaton, Counts I, III, and IV are DISMISSED with prejudice, and Count V remains.
And with respect to Officers Canty and Medrano, Counts I, III, and IV are DISMISSED with
prejudice, and Count V is DISMISSED without prejudice.
SO ORDERED.
/s/ Julia E. Kobick
JULIA E. KOBICK
Dated: February 2, 2026 	UNITED STATES DISTRICT JUDGE
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