United States Court of Appeals For the First Circuit

No. 18-1704

JOSEPH O'BRIEN,

Plaintiff, Appellant,

v.

TOWN OF BELLINGHAM, Commonwealth of Massachusetts; RICHARD PERRY, individually and in his official capacity as a police officer; TIMOTHY JOYCE, individually and in his official capacity as a police officer; JAMES RUSSELL, individually and in his official capacity as a police officer; BRIAN KUTCHER, individually and in his official capacity as a police officer; JOHN MELANSON, individually and in his official capacity as a police officer,

Defendants, Appellees,

ERIC ZIMMERMAN, individually and in his official capacity as a police officer; MICHAEL GILBOY, individually and in his official capacity as a police officer,

Defendants.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Jennifer C. Boal, U.S. Magistrate Judge]

Before

Howard, Chief Judge, Torruella and Selya, Circuit Judges. Edward J. McCormick III, with whom McCormick & Maitland was on brief, for appellant. Evan C. Ouellette, with whom Leonard H. Kesten, Deidre Brennan Regan, and Brody, Hardoon, Perkins & Kesten, LLP were on brief, for appellees.

November 22, 2019

-2- TORRUELLA, Circuit Judge. On April 9, 2012, Bellingham

police officers responded to a call regarding an unresponsive and

potentially intoxicated individual in the woods behind Shirley

Drive in Bellingham, Massachusetts. When the officers arrived,

they came upon Joseph O'Brien ("O'Brien") laying in a shallow

ravine with his pants unbuckled. There are conflicting versions

as to what occurred next, but the officers eventually placed

O'Brien in handcuffs and took him to the Bellingham Police Station

(the "Police Station"). There, O'Brien became increasingly

irrational and violent -- destroying property, attacking and

threatening the police officers, and harming himself.

Thereafter, O'Brien pleaded guilty to several state

criminal charges stemming from those incidents, including assault

and battery and resisting arrest. Subsequently, O'Brien filed

this civil rights suit in which he asserted excessive force claims

under

and Massachusetts state law against the

police officers that apprehended him in the woods and those who

attempted to subdue him at the Police Station. After lengthy

pre-trial briefing, the district court granted the officers'

motion for summary judgment, holding that Heck v. Humphrey,

(1994),1 barred O'Brien's excessive force claims as they

1 The Supreme Court in Heck, acknowledging its "expressed . . . concerns for finality and consistency," 512 U.S. at 484–85, found that "the hoary principle that civil tort actions are not

-3- relate to the events in the woods and some of the incidents at the

Police Station. The court held that the excessive force claims

arising from the events at the Police Station failed as a matter

of law because the undisputed facts did not establish the use of

excessive force, and in any event, that the defendants were

entitled to qualified immunity. O'Brien then filed the present

appeal. For the reasons that follow, we affirm.

I. Background

A. Factual Background2

O'Brien maintains that he has no recollection of the

events related to either his arrest in the woods or the post-arrest

incidents in the Police Station. For his claims arising from the

events in the woods, O'Brien relies on the testimony of two

eyewitnesses, Bonnie Bourque ("Bourque") and Paul Nilson

appropriate vehicles for challenging the validity of outstanding criminal judgments applies to § 1983 damages actions that necessarily require the plaintiff to prove the unlawfulness of his conviction or confinement," id. at 486. As a result, it held that where a § 1983 action for damages "would necessarily imply the invalidity of" a plaintiff's conviction or sentence, such an action is not cognizable under § 1983 "unless the plaintiff can demonstrate that the conviction or sentence has already been invalidated." Id. at 487. 2 Because this case is being reviewed at the summary judgment stage, the factual record is presented "in the light most favorable to [O'Brien,] the nonmoving party." Dennis v. Osram Sylvania, Inc.,

(1st Cir. 2008) (quoting Benoit v. Tech. Mfg. Corp.,

(1st Cir. 2003)).

-4- ("Nilson"), which we recount below. For his claims resulting from

the events at the Police Station, we have the benefit of video

security footage.

1. Events in the Woods

On April 9, 2012, Bourque -- who was inside her Shirley

Drive residence in Bellingham, Massachusetts -- heard shouting in

the woods behind her property. When she walked outside toward the

back of her property, Bourque saw O'Brien sitting in a small ravine

in the woods behind her backyard, accompanied by a younger man and

a dog. Bourque asked the younger man if O'Brien needed help and

whether she should call the police. The younger man informed

Bourque that O'Brien's name was "Joe" and left with the dog.

Though Bourque tried to talk to O'Brien, he refused to respond, he

lay down, and he did not move much. Bourque went back inside and

called the Bellingham Police Department.

Defendant-appellee Timothy Joyce, a Bellingham police

officer ("Officer Joyce"), arrived at Bourque's door shortly

thereafter. Bourque and Officer Joyce walked over to the woods

behind Bourque's house, and they found O'Brien laying down on his

back in the ravine with his pants undone. Officer Joyce walked

over to O'Brien's left side, shook him by the shoulder, and asked

him some questions, including why his pants were undone. When

O'Brien stood to buckle his pants, Officer Joyce shouted at him:

-5- "[G]et down on the ground. Put your hands behind your back.

You're under arrest." Officer Joyce immediately yelled,

"resisting arrest," pulled pepper spray out of his coat, and

sprayed O'Brien in the face. O'Brien's pants fell around his

ankles, making it impossible for him to run away. Two other

Bellingham police officers, including defendant-appellee Sergeant

James Russell ("Sergeant Russell"), arrived on the scene and also

started pepper spraying O'Brien. All three officers sprayed

O'Brien simultaneously. Bourque testified that O'Brien did not

threaten the officers or become aggressive before they pepper

sprayed him.

As the officers were spraying O'Brien, Bourque fled from

the woods and ran back toward her house, stopping at her back deck,

which was roughly the length of a football field away from

O'Brien's location in the woods. She did not see what was

happening in the woods while she was running, but she heard O'Brien

scream for "help." From her deck, Bourque witnessed

defendant-appellee Sergeant Richard Perry ("Sergeant Perry") cross

through the woods from Caroline Drive towards where O'Brien and

the other officers were. At that point, a hill and a shed

obfuscated Bourque's view of O'Brien and the officers. Bourque

testified that she did not see any officer strike or hit O'Brien.

-6- Nilson, who also witnessed portions of the incident,

lived on Caroline Drive on the other side of the woods from

Bourque. Nilson heard a commotion and ventured into his backyard

to where his property bordered the woods. From that vantage point,

he saw O'Brien in the woods surrounded by police officers screaming

"help, help, help." According to Nilson, the officers attempted

to talk O'Brien into voluntarily being handcuffed for

approximately ten to fifteen minutes, without success.

Eventually, Officer Joyce managed to get one handcuff on

O'Brien's wrist while keeping the other cuff in his hand. O'Brien

swung Officer Joyce around with one arm, while the other officers

attempted to subdue him by striking him multiple times in the back

and torso with their service batons. This had no apparent effect

on O'Brien, who continued to resist by swinging his arms and

swatting at the officers. According to Nilson, O'Brien continued

resisting until one or two officers struck him on the head with

their batons, knocking him to the ground. O'Brien finally stopped

fighting, and the officers handcuffed him.

2. Events at the Police Station

After O'Brien was taken into custody, the police

transported him to the Police Station for booking. The entire

-7- incident that occurred at the Police Station was captured on video

with audio.3

Officers brought O'Brien into the Police Station at

5:52 p.m. Simultaneously, Emergency Medical Technicians ("EMTs")

from the Bellingham Fire Department, who had been summoned to treat

O'Brien, arrived at the Police Station and entered the booking

area. O'Brien, who was handcuffed, was immediately placed in a

chair and questioned by a Bellingham firefighter/EMT regarding his

medical needs.

Defendant-appellee Officer John Melanson ("Officer

Melanson") uncuffed O'Brien's right hand and fastened that cuff to

a long chain attached to a bar on the wall, leaving O'Brien's right

hand unrestrained. The bar was located next to the door that

officers used to bring detainees into the Police Station.

Subsequently, O'Brien began screaming. The EMTs informed O'Brien

that he would be transported to a local hospital, but O'Brien

insisted on being taken to Massachusetts General Hospital in

3 In the "Statement of Undisputed Material Facts in Support of their Motion for Summary Judgment," the defendants cited to the time-stamped video recording to support their version of the events that transpired at the Police Station. O'Brien has not disputed the authenticity of the video evidence. Rather, in opposition to summary judgment, O'Brien objected to the defendants' "description and characterization of the images" without offering his own view of the contents of the video. He merely stated that "the video speaks for itself."

-8- Boston. O'Brien continued arguing with and cursing at the EMTs,

until they eventually retreated. Next, O'Brien cursed at the

officers and threatened them with violence. He told the officers

that he would "kick the shit out of" and "beat the fuck out of"

them, and he growled. He asked the officers if they would kill

him, and called them "pussies." O'Brien continued to scream,

growl, and threaten to commit graphic acts of violence against the

officers. He also told them that he had "a lot of fight left in

him."

Some minutes later, O'Brien spat on the floor, growled,

wiped mucus on the walls, and tore down a window covering. He

then grabbed the handset of a telephone and attempted to smash a

glass window with it, while taunting the officers to shoot him.

Officer Melanson, using a baton, struck O'Brien in the leg once to

stop him from breaking the window. O'Brien squared off and swung

the phone handset at the officers. Sergeant Perry also deployed

a baton. O'Brien hit the officers, and they struck him with batons

before retreating. O'Brien continued to swing at the officers,

telling them to shoot him.

Subsequently, O'Brien hit the window multiple times and

picked up a metal chair, prompting Officer Melanson to pepper spray

him. Unaffected, O'Brien struck the window with the chair, then

picked up a different chair, which the officers snatched from him.

-9- He then grabbed the phone handset, swung it around, and used it to

smash the glass window. O'Brien taunted, "where's your gun?" He

proceeded to destroy a window blind and strike at the broken window

with his uncuffed hand and arm. He told Sergeant Perry, "give me

your gun," and hurled a printer across the room. Once again,

O'Brien was pepper sprayed with no apparent effect.

Because the Bellingham Police Department was not

equipped with tasers, Sergeant Russell called the Franklin Police

Department to have an officer with a taser respond. He also called

the Worcester and the Norfolk County Sheriff's departments to have

a cell extraction team come to the Police Station to subdue

O'Brien, but they were unable to respond.

O'Brien proceeded to hit the broken window with his

uncuffed hand and arm once again, further shattering the panes.

Sergeant Perry struck O'Brien's leg with a baton and ordered

O'Brien to stay in the corner away from the window. Blood appeared

to drip from O'Brien's hand and arm due to cuts sustained while

smashing the window. O'Brien reached to his cuff and demanded

that the officers give him the key to uncuff himself. Officer

Joyce pepper sprayed O'Brien, who returned to the window and again

hit the glass shards with his hand. Officer Melanson struck

O'Brien in the torso with a baton and O'Brien swung his fist at

him. Once again, Officer Joyce pepper sprayed O'Brien, who

-10- returned to the window and tried to dislodge shards of glass.

Officer Melanson again struck O'Brien with a baton and told him to

back away. The struggle continued as the officers attempted

unsuccessfully to control O'Brien.

Almost forty minutes after arriving at the Police

Station, Franklin Police Officer defendant Eric Zimmerman

("Officer Zimmerman") arrived with a taser. The officers ordered

O'Brien to get on his knees and repeatedly told him to stop

resisting or he would be tased, and that he would receive the

medical attention he needed if he submitted. O'Brien refused.

After around twenty minutes, Officer Zimmerman deployed the taser.

O'Brien called the officer a "pussy" and asked him to "give [him]

another one." The officers informed O'Brien that he required

medical attention and that he would be tased if he did not comply.

O'Brien refused and he was tased a second time without significant

effect. O'Brien told the officers that he would keep the taser

barb as evidence and that he would swallow it. He then grabbed a

clock off the wall and appeared to swallow the taser barb.

O'Brien asked the officers if they were going to burn

down the Police Station, as "that [was their] only option."

Officer Perry asked O'Brien if he was going to allow the officers

to restrain him so that they could take him to the hospital,

remarking that O'Brien had "bled all over the floor." O'Brien

-11- refused and was informed that the officers were going to take the

next step if he did not comply by allowing them to place handcuffs

on both his hands, but he refused once again.

Subsequently, Defendant-appellee Bellingham Officer

Brian Kutcher ("Officer Kutcher") positioned a tactical weapon

that shot forty-millimeter rubber projectiles and asked, "are you

going to comply?" Officer Kutcher commanded O'Brien to get on the

ground approximately nine times, but O'Brien refused. Officer

Kutcher then fired a rubber projectile. O'Brien grabbed the clock

that he had previously torn off the wall from the floor and began

using it as a shield. Officer Kutcher repeatedly ordered O'Brien

to get down on the ground, to which O'Brien repeatedly responded,

"fuck you." Officer Kutcher then fired two more projectiles.

Among other statements, O'Brien shouted "you're gonna have to kill

me and you're gonna have to do murder right here." O'Brien was

commanded to get on the ground approximately fourteen more times,

to which he continually responded, "fuck you." Kutcher fired a

final rubber projectile at 7:13 p.m., with no effect. By this

time, the floor around O'Brien was covered with his blood and glass

from the shattered windows.

Sergeant Perry approached O'Brien to try to seize the

clock, but O'Brien held it up and said, "I'll smash it right in

your face." After asking O'Brien to put the clock down, Sergeant

-12- Perry displayed a baton, causing O'Brien to swing the clock at

him. In response, first Sergeant Perry and then Officer Kutcher

struck O'Brien with batons, and O'Brien whacked Sergeant Perry

multiple times with the clock until the officers were able to

snatch the clock away from him. The officers continued to command

O'Brien to get on the ground to be cuffed. Then, O'Brien began

swinging the phone handset once again. Officer Kutcher commanded

O'Brien to drop the phone, yet he refused and Officer Kutcher

deployed a long wooden baton and, approaching O'Brien, once again

commanded him to "drop the phone." O'Brien kicked at Officer

Kutcher, who struck at the phone. In this scuffle, O'Brien dropped

the phone handset and charged at Officer Kutcher, who struck at

O'Brien and cleared the phone out of O'Brien's reach with the

wooden baton before retreating.

O'Brien was told again to get on the ground so he could

be cuffed and transported to a hospital to be evaluated and

treated. O'Brien responded, among other things, that he was

already dead. When O'Brien was told that a K-9 dog would be

brought into the booking area if he did not get down on the ground,

he responded, "I like dogs." Franklin Police Officer defendant

Michael Gilboy ("Officer Gilboy") arrived at 7:25 p.m. holding a

restrained police dog. While the dog barked at O'Brien, O'Brien

approached the dog and reached out to pet it. He then told Officer

-13- Gilboy that "your fucking dog is a pussy." Officer Gilboy

eventually retreated, and the dog was never released. After

approximately twenty more minutes, a mellowed O'Brien requested

water, which he was quickly given. A few minutes later, O'Brien

finally submitted and got on the ground. O'Brien was then

handcuffed, placed on a stretcher, and taken to Milford Hospital.

The entire episode lasted nearly two hours.

At the hospital, O'Brien was treated for a ketamine

overdose and lacerations to his right hand that required suturing.

He was also diagnosed with a mildly displaced avulsion fracture to

his left wrist and nondisplaced fractures to his right wrist. As

O'Brien conceded, however, "it is impossible to say with a

reasonable degree of medical certainty whether" these fractures

resulted from force used by any police officer or were

self-inflicted by O'Brien's own actions.4

4 We have previously held that "the commonly accepted meaning among lawyers and judges to the term 'reasonable degree of scientific certainty'" is "a standard requiring a showing that the injury was more likely than not caused by a particular stimulus, based on the general consensus of recognized [scientific] thought." Burke v. Town of Walpole,

(1st Cir. 2005) (alteration in original) (quoting Black's Law Dictionary 1294 (8th ed. 2004) (defining "reasonable medical probability" or "reasonable medical certainty," as used in tort actions)). This is consistent with the "preponderance of the evidence" standard which "simply requires the trier of fact 'to believe that the existence of a fact is more probable than its nonexistence before [he] may find in favor of the party who has the burden to persuade the [trier of fact] of the fact's existence.'" Concrete Pipe & Prods. of Cal., Inc. v. Constr. Laborers Pension Tr. for S. Cal.,

-14- 3. Guilty Pleas as to State Criminal Charges

O'Brien pleaded guilty to the following charges arising

out of his April 2012 arrest in the woods: (1) assault and battery

by means of a dangerous weapon -- on Officer Joyce by means of

handcuffs and on Sergeant Russell by means of a tree branch -- in

violation of Mass. Gen. Laws ch. 265, § 15A(b); (2) resisting

arrest in violation of Mass. Gen. Laws ch. 268, § 32B; and

(3) assault and battery on a public employee as to Officer Joyce,

Sergeant Russell, and Sergeant Perry, in violation of Mass. Gen.

Laws ch. 265, § 13D. O'Brien also pleaded guilty to the following

charges arising out of the incident in the Police Station's booking

room: (1) assault and battery by means of a dangerous weapon (a

phone handset) as to Officer Melanson and Sergeant Perry, in

violation of Mass. Gen. Laws ch. 265, § 15A(b); (2) malicious

destruction of property valued in excess of $250 -- a window,

chairs, and ceiling tiles -- in violation of

; and (3) malicious destruction of property valued

in excess of $250 -- a breathalyzer machine "BT" printer -- also

in violation of

.

As part of the plea colloquy, the Assistant District

Attorney recited the following facts regarding O'Brien's arrest:

(1993) (quoting In re Winship,

, 371–72 (1970) (Harlan, J., concurring)).

-15- Your Honor, regarding indictment 12-0608, on October (sic) 9, 2012, the Bellingham police responded to a wooded area behind [redacted] Shirley Road in the Town of Bellingham for a reported unknown male who appeared to be sleeping in a drainage ditch and, when he was awoken, appeared to be intoxicated or under the influence of something, and he was stumbling around.

Officer Timothy Joyce initially responded, Sergeant Neil (sic) Russell shortly thereafter. They both assisted Mr. O'Brien to his feet. His speech was slurred and he was unsteady on his feet. Officer Joyce made the determination to place him into protective custody, and he conducted a pat-down search for his safety. Mr. O'Brien began to tense up and resist. Mr. O'Brien was taken to the ground and pushed himself up while police were on his back. Officer Joyce removed a switchblade pocket knife from Mr. O'Brien's right pocket and pants, and the blade was still open at this time.

During the struggle, Sergeant Russell disengaged from Mr. O'Brien and drew his OC spray. Officer Joyce continued to struggle with Mr. O'Brien and his left hand was caught in the open handcuff. As Mr. O'Brien pulled away from Officer Joyce, the officer's middle ring and little fingers twisted in the open handcuff. . . . O'Brien and Officer Joyce fell to the ground with their combined weight and landed on Officer Joyce's wrist. When Officer Joyce separated from Mr. O'Brien, the open handcuff got caught on the officer's glove and ripped the area around his wrist. It was later determined the wrist was fractured due to these actions.

Once the officers created about fifteen feet of separation and distance from Mr. O'Brien, he grabbed a tree branch and struck Sergeant Russell on the right side of his face. Sergeant Russell sprayed him with OC, which had no effect, apparently, on Mr. O'Brien, who got into a fighter's stance and closed fists and screamed that he had been waiting all his life training for something like this. Officer Joyce drew his baton and gave orders for Mr. O'Brien to get on the ground, which he refused. Both officers used a series of leg strikes to Mr. O'Brien, which had little or no effect on him. The officers requested more backup.

-16- Sergeant Perry arrived on the scene and recognized him from the September 2, 2011 incident in which he had assaulted police. Mr. O'Brien continued to yell threats at Sergeant Perry. The three police were finally able to get Mr. O'Brien to the ground, where he continued to resist and fight. Officer John Melanson then arrived on the scene, and he and Sergeant Perry escorted Mr. O'Brien back to the Bellingham police station for booking.5

When asked by the court whether those facts "fairly and

accurately describe[d] [his] conduct," O'Brien answered "yes."

Additionally, when the judge asked O'Brien whether he understood

that by pleading guilty he was "admitting to the truth of those

matters that were just stated in court," he once again responded

"yes." O'Brien also answered in the affirmative when the judge

asked him whether he was "pleading guilty . . . because [he was]

guilty[] and for no other reason," and whether he had discussed

"these matters" with his attorney, including his rights, "any

defenses [he] may have, and the consequences of pleading guilty."

The state judge accepted O'Brien's plea for which he found that

there was a factual basis.

B. Procedural History

On April 6, 2015, O'Brien filed suit against Sergeants

Perry and Russell and Officers Joyce, Kutcher, and Melanson of the

Bellingham Police Department, as well as Officers Zimmerman and

5 The Assistant District Attorney also recounted the incidents at the Police Station.

-17- Gilboy of the Franklin Police Department. O'Brien alleged that

they had used excessive force and had committed assault and battery

against him in apprehending him in the woods and in subduing him

at the Police Station. 6 On September 11, 2015, the parties

consented to the jurisdiction of a magistrate judge for all

purposes. After more than two years of litigation, the parties

filed a stipulation of dismissal with prejudice as to the Franklin

Police Department defendants Officers Zimmerman and Gilboy.

In the weeks prior to trial -- which was scheduled to

begin on April 2, 2018 -- the remaining defendants, Sergeants Perry

and Russell and Officers Joyce, Kutcher, and Melanson

(the "Defendants") filed various motions in limine. After

reviewing those motions and O'Brien's responses, the district

court determined that some issues raised were more appropriate for

the summary judgment context, and that they were "for the court,

not the jury, to decide." Accordingly, the district court

postponed the trial and set a schedule for summary judgment

briefing, directing the parties to focus on the applicability of

the judicial estoppel doctrine and whether O'Brien's excessive

force claims were viable in light of Heck.

6 O'Brien did not claim false arrest. While O'Brien also sued the Town of Bellingham, the court granted the Town's motion to dismiss on October 14, 2015.

-18- As ordered, the Defendants moved for summary judgment on

the grounds that Heck barred O'Brien's claims and they were

entitled to qualified immunity. O'Brien opposed, and additionally

filed a motion to vacate the dismissal of Officers Zimmerman and

Gilboy, claiming that the stipulation of dismissal for those

defendants was predicated on the parties' agreement that "no motion

for summary judgment would be filed." On May 30, 2018, the

district court issued an order noting that the Defendants had not

asserted as a basis for their motion that the undisputed facts

showed no excessive force. Nonetheless, it notified O'Brien that

it was considering granting summary judgment sua sponte as to the

excessive force claims related to the incidents at the Police

Station on the ground that, based on the undisputed facts -- i.e.,

the video of the incident -- no reasonable jury could find that

the Defendants had used excessive force. O'Brien filed a response

on June 15, 2018.

On June 1, 2018, the Defendants filed a motion to amend

their answer to the complaint to add the affirmative defense of

judicial estoppel, which O'Brien opposed. Subsequently, the

district court heard oral arguments on the Defendants' motion to

amend and O'Brien's motion to vacate. On June 21, 2018, the

district court denied O'Brien's motion to vacate the dismissals of

Officers Zimmerman and Gilboy.

-19- On June 27, 2018, the district court granted the

Defendants' motion to amend their answer to the complaint and their

motion for summary judgment. The district court found that

O'Brien's claims arising out of the episode in the woods were

barred by Heck. It explained that any claim based on the premise

that O'Brien was "lawfully permitted to resist arrest and/or use

force to defend himself from excessive force . . . would

necessarily undermine his convictions" arising from the same

events. The district court also discarded any theory of liability

based on Bourque's testimony that O'Brien "was attacked and pepper

sprayed without provocation by the officers" as "too . . . directly

inconsistent with [O'Brien's] plea in the criminal case."

Concerning the incident at the Police Station, the

district court's decision was twofold. First, the district court

found that Heck barred O'Brien's claims against Officer Melanson

and Sergeant Perry related to the events leading up to when O'Brien

struck them with the phone handset.7 Further, the district court

concluded that any claims against Officer Melanson and Sergeant

Perry "past the point where they were hit by O'Brien with the phone

h[andset]," or against the other defendants involved in that

incident, ultimately failed as a matter of law because the

7 As the district court noted, its task was complicated by the fact that O'Brien did not identify his theories of relief.

-20- undisputed facts showed that the officers' actions were

objectively reasonable and, thus, that the officers had not used

excessive force.

Alternatively, the district court concluded that "the

Defendants are entitled to qualified immunity in connection with

any excessive force claims arising out of the events at the police

station." On July 24, 2018, O'Brien filed the present appeal.

II. Discussion

A. Denial of O'Brien's Motion to Vacate the Stipulation of Dismissal

We need not linger over the merits of this issue as we

lack jurisdiction to entertain it. The Defendants assert that

O'Brien failed to comply with two jurisdictional requirements:

first, that he did not file a notice of appeal within thirty days

of the order's issuance, and second, that he did not reference the

district court's ruling on the motion to vacate in the notice that

he eventually filed. The Defendants' second point suffices to

dispose of this issue.

The Federal Rules of Appellate Procedure require that a

party "designate the judgment, order, or part thereof being

appealed" in a notice of appeal, Fed. R. App. P. 3(c)(1)(B), and

this requirement is generally characterized as jurisdictional in

nature. See Smith v. Barry,

(1992). "This

raises the question of whether the notice, as drafted, confers

-21- jurisdiction upon this court to review" the challenged ruling.

Chamorro v. Puerto Rican Cars, Inc.,

(1st Cir. 2002).

The Supreme Court has stated that we must construe Rule 3(c)'s

specificity requirement liberally, see Barry,

,

and, therefore, "[a] mistake in designating a judgment . . . in

the notice of appeal ordinarily will not result in loss of the

appeal as long as the intent to appeal a specific judgment can be

fairly inferred from the notice and [the] appellee is not misled

by the [unclear notice]," Spookyworld, Inc. v. Town of Berlin (In

re Spookyworld, Inc.),

(1st Cir. 2003) (quoting Kelly

v. United States,

, 96 n.3 (1st Cir. 1986)). In

examining the notice, we consider "the appellant's intent on the

record as a whole." Marie v. Allied Home Mortg. Corp.,

(1st Cir. 2005).

O'Brien's notice of appeal makes no reference to the

district court's ruling on the motion to vacate the stipulation of

dismissal. Rather, O'Brien stated that he was appealing "from the

Court's ruling allowing the defendants' Motion for Summary

Judgment entered on June 27, 2018, and the Court's Judgment

dismissing the instant matter also entered on June 27, 2018, as

well as any and all rulings by the Court." Neither of the two

rulings specifically identified in the notice of appeal relate or

refer to the ruling on the motion to vacate. Omitting the ruling

-22- on that motion, "while, at the same time, designating . . .

completely separate and independent order[s] loudly proclaims

[O'Brien's] intention not to appeal," Kotler v. Am. Tobacco Co.,

(1st Cir. 1992), from the ruling on the motion to

vacate. Furthermore, O'Brien's inclusion of the phrase "as well

as any and all rulings by the Court" in his notice of appeal does

not overcome the deficiency. This language is insufficient to

give notice to either the Defendants or the court of O'Brien's

intent to appeal another, specific order. See

Nor can that

intent be inferred from the notice or the record, leaving us

without jurisdiction to review it. Kelly,

n.3

(finding that the court may be flexible in entertaining an appeal

even if the specific judgment that is the subject of the potential

appeal is not designated in the notice of appeal so long as "the

intent to appeal from a specific judgment can be fairly inferred

from the notice, and [the] appellee is not misled by the mistake");

see also Barry,

("Rule 3's dictates are

jurisdictional in nature . . . . Although courts should construe

Rule 3 liberally when determining whether it has been complied

with, noncompliance is fatal to an appeal."). That ends this

matter.

-23- B. The Defendants' Motion to Amend Their Answer

O'Brien next challenges the district court's ruling

allowing the Defendants to amend their answer to the complaint to

include the affirmative defense of judicial estoppel after the

close of discovery and the filing of their motion for summary

judgment.

The Defendants mention, without elaborating, that

O'Brien's notice of appeal "does not separately or specifically

reference the ruling on the motion to amend their answer." While

this passing reference to an argument would ordinarily be

insufficient to warrant our consideration, see United States v.

Zannino,

(1st Cir. 1990), we pause here because of

the jurisdictional ramifications.

It is true that O'Brien's notice of appeal does not

specifically reference the district court's order granting the

Defendants' motion to amend their answer. Instead, it designates

the Court's ruling on the motion for summary judgment and the

judgment dismissing the case, both entered on June 27, 2018. As

before, we consider "the appellant's intent on the record as a

whole and . . . whether the appellee has been misled by the

appellant's unclear notice." Marie,

. Here, we note

that although O'Brien did not specifically identify the order on

the Defendants' motion to amend in his notice of appeal, the

-24- summary judgment ruling, which he did specifically include in his

notice of appeal, elaborated on the district court's reasons for

granting the Defendants' motion to amend, and both orders were

issued on the same day. Hence, it is unlikely that the Defendants

were misled "by the inartfully drafted notice of appeal." Young

v. Gordon,

(1st Cir. 2003). And in any event,

because the underlying controversy is easily resolved in favor of

the Defendants, we need not tackle the jurisdictional issue here.

See Markel Am. Ins. Co. v. Díaz-Santiago,

(1st

Cir. 2012) ("[W]e take shelter . . . under the familiar principle

that where an appeal presents a difficult jurisdictional issue,

yet the substantive merits underlying the issue are facilely

resolved in favor of the party challenging jurisdiction, the

jurisdictional issue may be avoided." (quoting Kotler v. Am.

Tobacco Co.,

(1st Cir. 1990))).

To begin with, O'Brien faces a high standard of review

hurdle. We review the district court's decision granting the

Defendants' motion to amend their answer for abuse of discretion.

Klunder v. Brown Univ.,

(1st Cir. 2015). This

means that a district court's order granting a motion to amend an

answer to a complaint will be upheld "so long as 'the record

evinces an arguably adequate basis for the court's decision.'"

-25-

(quoting Juárez v. Select Portfolio Servicing, Inc.,

(1st Cir. 2013)).

Federal Rule of Civil Procedure 15(a) provides that

after the time to amend "as a matter of course" has expired, "a

party may amend its pleading only with the opposing party's written

consent or the court's leave." Fed. R. Civ. P. 15(a)(2).

According to the rule, "[t]he court should freely give leave when

justice so requires."

"[W]hen a litigant seeks leave to

amend after the expiration of a deadline set in a scheduling

order," however, "Rule 16(b)'s more stringent good cause standard

supplants Rule 15(a)'s leave freely given standard." United

States ex rel. D'Agostino v. EV3, Inc.,

(1st

Cir. 2015); see also Fed. R. Civ. P. 16(b)(4) ("A schedule may be

modified only for good cause and with the judge's consent.").

Still, district court judges "enjoy great latitude in carrying out

case-management functions." Jones v. Winnepesaukee Realty,

(1st Cir. 1993).

As a general rule, affirmative defenses enumerated in

Federal Rule of Civil Procedure 8(c), including estoppel, are

"deemed waived unless raised in the answer." Davignon v. Clemmey,

(1st Cir. 2003); see also Fed. R. Civ. P. 8(c)(1)

("In responding to a pleading, a party must affirmatively state

any . . . affirmative defense, including . . . estoppel."). This

-26- Court, however, has identified exceptions to Rule 8(c)'s bar of

untimely affirmative defenses, including when: (1) "the defendant

asserts it without undue delay and the plaintiff is not unfairly

prejudiced by any delay," or (2) "the circumstances necessary to

establish entitlement to the affirmative defense did not obtain at

the time the answer was filed." Davignon,

.

O'Brien correctly asserts that the Defendants filed

their motion to amend after the case-management order deadline for

amending the pleadings had passed, and thus that "Rule 16(b)'s

more stringent good cause standard supplant[ed] Rule 15(a)'s leave

freely given standard." D'Agostino,

. Even under

the more stringent standard, however, O'Brien's contentions that

the district court abused its discretion are unconvincing, as the

record clearly "evinces an arguably adequate basis for the court's

decision." Klunder,

(quoting Juárez,

).

First, "the circumstances necessary to establish [the

Defendants'] entitlement to [judicial estoppel] did not obtain at

the time the answer was filed." Davignon,

. As the

Defendants pointed out, they did not receive a copy of the plea

colloquy concerning O'Brien's state court convictions until after

they had answered the complaint, and they did not know that O'Brien

was planning to introduce facts that contradicted the basis of his

-27- prior convictions until the deposition of certain witnesses during

discovery. Moreover, by raising the judicial estoppel defense

first in connection with their motion in limine and later in their

motion for summary judgment, the Defendants put O'Brien on notice

of the defense. And considering that the court postponed trial

and set a schedule for summary judgment briefing, "in part, to

give . . . the parties sufficient time for a thoughtful

consideration of the issues," O'Brien had a more than adequate

opportunity to address the defense. Thus, while O'Brien contends

that he "suffered [from] the delay" in the Defendants' request to

amend their answer, he did not explain, and we do not see, how he

suffered any prejudice. In the end, O'Brien has simply not shown

that the district court abused its "great latitude" over

case-management functions under Rule 16(b). Jones,

.

C. District Court's Grant of Summary Judgment

This Court "review[s] the district court's grant of

summary judgment de novo." Scholz v. Goudreau,

(1st Cir. 2018) (citing Ocasio-Hernández v. Fortuño-Burset,

(1st Cir. 2015)). Because we "afford plenary review to

orders granting or denying summary judgment[,] . . . we 'must view

the entire record in the light most hospitable to the party

opposing summary judgment, indulging all reasonable inferences in

-28- that party's favor.'" Podiatrist Ass'n, Inc. v. La Cruz Azul de

P.R., Inc.,

(1st Cir. 2003) (quoting Griggs-Ryan v.

Smith,

(1st Cir. 1990)).

1. Heck Bars O'Brien's Excessive Force Claims Arising from the Incident in the Woods

In Heck, the Supreme Court held that when a person

convicted of a crime files a § 1983 claim seeking damages for an

"allegedly unconstitutional conviction" or for "other harm," the

district court "must consider whether a judgment in favor of the

plaintiff would necessarily imply the invalidity of his conviction

or sentence; if it would, the complaint must be dismissed unless

the plaintiff can demonstrate that the conviction or sentence has

already been invalidated." 512 U.S. at 486–87. A plaintiff's

excessive force claim and his conviction "may be so interrelated

factually as to bar the § 1983 claim." Thore v. Howe,

(1st Cir. 2006). Therefore, to determine Heck's

applicability, a court must examine "the relationship between the

§ 1983 claim and the conviction, including asking whether the

plaintiff could prevail only by 'negat[ing] an element of the

offense of which he [was] convicted.'" Id. at 179 (alterations

in original) (quoting Heck,

n.6). Whether Heck

bars § 1983 claims is a jurisdictional question that can be raised

at any time during the pendency of litigation. See White v.

Gittens,

(1st Cir. 1997); see also Henderson ex

-29- rel. Henderson v. Shinseki,

(2011) (noting that

objections to subject-matter jurisdiction "may be raised at any

time").

In this case, the record reflects that O'Brien's

excessive force claims arising from the incident in the woods are

"so interrelated factually" with his state convictions arising

from those events that a judgment in O'Brien's favor would

"necessarily imply" the invalidity of those convictions. See

Thore, 466 F.3d at 179–80. Indeed, if the officers had used

excessive force against O'Brien while arresting him in the woods,

as he now claims, their unlawful behavior would have provided

O'Brien with a defense against the charges for resisting arrest

and assault and battery under state law. See Commonwealth v.

Moreira,

(Mass. 1983) ("[W]e conclude that

where the officer uses excessive or unnecessary force to subdue

the arrestee, regardless of whether the arrest is lawful or

unlawful, the arrestee may defend himself by employing such force

as reasonably appears to be necessary."); Commonwealth v. Graham,

(Mass. App. Ct. 2004) ("At least in

circumstances where the evidence supports a claim of excessive or

unnecessary force by police and the concomitant right to

self-defense, we think the judge must also instruct that the

Commonwealth must prove beyond a reasonable doubt that the police

-30- did not engage in excessive force, as well as that the defendant

did not act in self-defense."); Commonwealth v. Francis,

(Mass. App. Ct. 1987) ("Even in circumstances where the

defendant would be justified in using force in lawful defense of

his person against a third person, he may not do so against a

police or correction officer unless the officer uses excessive or

unnecessary force.").

Similarly, the district court correctly found that Heck

bars any claim that Officer Melanson and Sergeant Perry used

excessive force leading up to when O'Brien struck them with the

phone handset. Granting a judgment against Officer Melanson and

Sergeant Perry would have implied that O'Brien's conduct was

justified, while the officers' actions were unjustified, which

would have necessarily undermined the validity of O'Brien's

assault and battery convictions. As we explained in Thore,

although "[a] § 1983 excessive force claim brought against a police

officer that arises out of the officer's use of force during an

arrest does not necessarily call into question the validity of an

underlying state conviction . . . [,] it is not necessarily free

from Heck" either.

. And because O'Brien has not

specified any theory of relief, let alone attempted to identify a

factual scenario which would survive Heck, we need not go any

further, as any argument to that effect is waived. See Zannino,

-31-

("It is not enough merely to mention a possible

argument in the most skeletal way, leaving the court to do

counsel's work, create the ossature for the argument, and put flesh

on its bones.").

The arguments that O'Brien does raise on appeal are

confusing, conclusory, and easily discarded. First, O'Brien's

assertion that the Defendants waived a defense based on Heck is

unavailing as we have already noted that it is a jurisdictional

issue that can be raised sua sponte by the court. See White,

.

Next, O'Brien claims that because the Assistant District

Attorney stated in the plea colloquy that the incident in the woods

occurred on "October 9" rather than "April 9," the Defendants "have

not furnished sufficient evidence to warrant a finding of summary

judgment in their favor based on the holding in" Heck. Moreover,

O'Brien avers that because his indictment does not delineate the

exact locations of the crimes, it is "difficult, if not

impossible," to determine whether they occurred in the woods or at

the Police Station. Accordingly, O'Brien asserts, the Defendants

"have not satisfied their burden to establish that the claims for

excessive force are so factually interrelated so as to bar [his]

§[]1983 claims."

-32- These points are meritless. The facts set out by the

Assistant District Attorney in the plea colloquy clearly and

unambiguously delineate which offenses relate to which incident.

Moreover, the record as a whole supports the conclusion that, in

his plea colloquy, the Assistant District Attorney was referring

to O'Brien's arrest by the Bellingham Police Department in the

woods on April 9, 2012, even if he misspoke by saying "October"

instead of "April." Crucially, O'Brien did not contest the date

of the incident in response to the Defendants' statement of facts,

and he did not present evidence supporting the conclusion that the

Assistant District Attorney could have been referring to any other

incident. Accordingly, the district court correctly granted

summary judgment as to O'Brien's claims arising from the incident

in the woods.

2. The Excessive Force Claims Arising from the Incident at the Police Station

"Excessive force claims are founded on the Fourth

Amendment right to be free from unreasonable seizures of the

person." Raiche v. Pietroski,

(1st Cir. 2010)

(citing U.S. Const. amend. IV). It follows then that excessive

force claims against law enforcement officers effecting a seizure

are "governed by the Fourth Amendment's 'reasonableness'

standard." McGrath v. Tavares,

(1st Cir. 2014)

(quoting Plumhoff v. Rickard,

(2014)).

-33- "Determining whether the force used to effect a particular seizure

is 'reasonable' under the Fourth Amendment requires a careful

balancing of the nature and quality of the intrusion on the

individual's Fourth Amendment interests against the countervailing

governmental interests at stake." Graham v. Connor,

(1989) (some internal quotation marks omitted) (quoting

Tennessee v. Garner,

(1985)). The critical question

is "whether the defendant officer employed force that was

unreasonable under the circumstances." Raiche,

(internal quotation marks omitted) (quoting Jennings v. Jones,

(1st Cir. 2007)).

"Th[e] reasonableness inquiry is an objective one; it is

not a question of subjective intent." McGrath,

(citing Graham,

). An assessment of reasonableness

"must be judged from the perspective of a reasonable officer on

the scene, rather than with the 20/20 vision of hindsight."

Graham,

. This evaluation must allow "for the fact

that police officers are often forced to make split-second

judgments -- in circumstances that are tense, uncertain, and

rapidly evolving -- about the amount of force that is necessary in

a particular situation."

. Application of the

reasonableness test "requires careful attention to the facts and

circumstances of each particular case, including the severity of

-34- the crime at issue, whether the suspect poses an immediate threat

to the safety of the officers or others, and whether he is actively

resisting arrest or attempting to evade arrest by flight."

at 396 (citing Garner, 471 U.S. at 8–9).

In this light, we conclude that the district court did

not err in finding that the undisputed evidence established that

the Defendants did not use excessive force against O'Brien at the

Police Station. As the district court noted, "[t]he video of the

incident show[ed] that no force [was] used against O'Brien until

after he start[ed] acting irrationally, cursing and threatening

the officers, and trying to smash a glass window." Moreover, it

is clear that the Defendants did not "employ[] force that was

unreasonable under the circumstances," given O'Brien's

unpredictable and violent actions at the Police Station. See

Raiche,

(quoting Jennings,

). Thus,

even viewed in the light most favorable to O'Brien, we find that

the Defendants' actions at the Police Station were objectively

reasonable, especially under the incident's "tense, uncertain, and

rapidly evolving" circumstances. See Graham,

.

O'Brien counters, first, that the district court should

not have relied solely on the Police Station video because

deposition testimony established that summary judgment on the

issue of excessive force was "simply not warranted." On appeal,

-35- O'Brien does not identify the deposition testimony to which he

refers. Moreover, in opposition to summary judgment below,

O'Brien objected to the Defendants' "description and

characterization of the images" without disputing the Defendants'

proposed facts with either any evidence or even by offering his

own view of the contents of the video. He merely stated that "the

video speaks for itself." The district court found that the

Defendants' "characterizations [of the video] generally appear

accurate," and so do we. In any event, we reject O'Brien's

argument, because when the record contains video evidence, the

authenticity of which is not challenged, the court should

ordinarily view the facts "in the light depicted by the video

evidence." Underwood v. Barrett,

(1st Cir. 2019)

(per curiam).

O'Brien also reiterates his argument that because he

"was handcuffed to a handrail, and thus could not escape, attack

or physically resist at all," all the Defendants needed to do was

"simply . . . leave him alone"; "[i]nstead, they chose to beat him

with batons, shoot him with rubber bullets, and hit him with

multiple taser barbs." We similarly reject this argument. As the

district court stated, "the length of the chain attached to the

bar was long enough that every time the officers retreated, O'Brien

responded by attempting to use items in the booking room as weapons

-36- or by destroying property." Moreover, O'Brien's argument ignores

that he "attempted to escape from the handcuffs on several

occasions," that he "was causing a major security issue," and that

he "was bleeding profusely from injuries he appear[ed] to have

sustained from breaking a glass window and the officers needed to

subdue him in order to transport him for medical attention."

Finally, O'Brien avers that he voluntarily complied

after the officers gave him a glass of water and talked to him.

Yet the video reflects that the officers spoke to O'Brien

rationally many times before and that they made numerous prior

verbal attempts to calm him down throughout the two-hour ordeal,

with no success. The officers even appeared to minimize the amount

of force they used. For example, they fired the rubber bullets

only sparingly and withheld the K-9 dog. Thus, we conclude that

even when viewed in the light most favorable to O'Brien, based on

the undisputed facts, no reasonable jury could find that the

officers' actions were unreasonable under the circumstances.

Accordingly, the district court did not err in entering summary

judgment against O'Brien on his excessive force claims arising

from the incident at the Police Station.8

8 Because O'Brien's excessive force claims fail as a matter of law, we need not decide whether the Defendants were entitled to qualified immunity.

-37- 3. State Law Claims

Because O'Brien makes no argument regarding the

dismissal of his state law claims, any such argument is waived.

Zannino,

.

III. Conclusion

For the foregoing reasons, we affirm.

Affirmed.

-38-