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United States of America v. RICHARD SYLVESTER
Case Number: 19-2127
Judge: Sandra Lea Lynch
Court: United States Court of Appeals
For the First Circuit
Plaintiff's Attorney: Julia M. Lipez, Assistant United States Attorney, with whom
Halsey B. Frank, United States Attorney
Boston, MA - Criminal defense lawyer represented defendant with one count of possession with intent to distribute various controlled substances and one count of possession of a firearm in furtherance of a drug trafficking crime charges.
The parties stipulated to the facts contained in the
various exhibits submitted to the district court, which establish
1. The Arrest and Impound
In or around May 2017, a federal warrant was issued for
Sylvester's arrest for suspected drug activity said to have
occurred in August 2016. Around 7:30 P.M. on Friday, May 19, 2017,
Maine Drug Enforcement Agency ("MDEA") Special Agent Jacob Day
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("Agent Day") was driving off duty along Route 1A in Dedham, Maine.
Route 1A is a major highway that runs along the coast of Maine to
the Canadian border. Agent Day passed a black Cadillac Escalade
driven by Sylvester. Sylvester was alone in the car. Agent Day
recognized Sylvester and was aware of the outstanding federal
warrant for his arrest from speaking with a United States Drug
Enforcement Agency ("DEA") agent a few weeks before.
Agent Day ran a registration check on the Escalade's
plate number which revealed that the owner of the car was Hailee
Goodwin, who lived in Hancock, Maine. She was later determined to
be Sylvester's girlfriend. Agent Day called the DEA agent with
whom he had previously spoken and she confirmed that the federal
arrest warrant was still active and that Sylvester should be
Agent Day contacted Lieutenant Tim Cote ("Lt. Cote") of
the Hancock County Sheriff's Department to request the arrest of
Sylvester pursuant to that warrant. At some point, Agent Day also
requested that a K-9 unit be brought in to conduct a sniff test of
the exterior of the Escalade.
Acting on the federal warrant and at Agent Day's request,
Lt. Cote went with Sheriff's Deputies Corey Bagley ("Dep. Bagley")
and Jeffrey McFarland ("Dep. McFarland") and another officer to
Route 1A to locate the Escalade. They stopped the Escalade
sometime after 7:30 at night along Route 1A in or near Ellsworth,
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Maine. Sylvester, the sole occupant, was told to get out of the
car and was arrested.
Videos of the traffic stop recorded on the officers'
dashboard cameras show that Route 1A is and was on that Friday
night a well-trafficked, two-lane highway, and that the parked
Escalade was sticking out into the traffic lane so that the cars
passing by had to swerve into the oncoming traffic lane to avoid
it. During Sylvester's arrest, Dep. Bagley found two knives, a
pair of brass knuckles, and a wad of $2,799 in cash on Sylvester.
Sylvester told the officers there were no other weapons in the car
(that proved not to be true). He also told them he was headed "up
the road" to meet Goodwin's mother, but not Goodwin, at a
McDonald's. There is no evidence as to how far away the McDonald's
was or whether Goodwin's mother was authorized by Goodwin to drive
the car or whether Goodwin's mother was available to come retrieve
the Escalade promptly or how she would do so. Nor is there evidence
that Sylvester specifically requested that Goodwin's mother or
anyone else come remove the stopped car.
The officers transported Sylvester to the Hancock County
Jail where he was booked on the federal arrest warrant. The
Hancock County officers did not inform Sylvester that he could
contact someone, nor did he make any such request. They also did
not ask him whether he had a preferred towing service.
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During the stop, Lt. Cote requested the Maine State
Police to do the K-9 sniff as MDEA Agent Day had requested. He
was told that it would take some time because the K-9 unit was
traveling from a different county. Lt. Cote authorized a towing
service to remove the car from the side of the highway and take it
to an impound facility in Hancock.
2. The Impound and Inventory Policies
The stop of the Escalade was at the request of a MDEA
agent and a federal DEA agent who are not subject to the Hancock
County Sheriff's Department's policies, but Hancock County
Sheriff's Department officers made the stop and are subject to
those policies.1 There are two Hancock County policies that are
relevant to this appeal: the "TOWING/WRECKERS" policy ("the
Impound Policy") and the "VEHICLE INVENTORY" policy ("the
Inventory Policy"). The Impound Policy authorizes law enforcement
to tow and to store a vehicle under certain circumstances,
including where the vehicle "[i]mped[es] or [e]ndanger[s]
[t]raffic." The Impound Policy specifies that "[n]o vehicle shall
be stopped or left unattended in such a manner as to impede or
render dangerous the use of the highway by others, except in cases
of mechanical breakdown, law enforcement emergency or traffic
crash," and "[i]f such disabled vehicle is not promptly removed
1 The government has assumed and has not argued to the
contrary that the Hancock County policies apply.
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the law enforcement officer may order the vehicle towed at the
expense of the owner." The policy further states that
[w]henever possible, owners or operators of
vehicles for which towing is required will be
encouraged to specify a towing service of
their own choice. When required, the law
enforcement officer will summon a tow truck,
unless a specific request for a particular tow
service has been made by the owner or operator
of the vehicle to be towed, and if such tow
service is reasonabl[y] available.
The policy reiterates that "[w]hen a wrecker service is
needed, the law enforcement officer shall ask the vehicle
owner/operator if they have a preference of wrecker service," and
if they do, the law enforcement officer will arrange for that
tow/wrecker service to be contacted. But "[w]hen a wrecker service
is NOT at the owners' request, [it] would be considered a law
enforcement tow." An inventory search is required of all vehicles
taken into police custody because of a law enforcement tow "if the
vehicle is unlocked prior to the wrecker towing the vehicle" or
"if the wrecker operator has to open the vehicle prior to towing
The Inventory Policy, in turn, provides that before
taking a vehicle into custody "[w]here the owner or operator in
possession of a vehicle is arrested . . . , and the vehicle is not
required as evidence and need not be impounded for any other
reason, the law enforcement officer" shall
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[a]dvise the owner or operator that they may
release the vehicle to a licensed driver who
is willing to assume full responsibility for
the vehicle and all property contained
therein. This person must be at the scene or
be able to arrive prior to the law enforcement
officer leaving. . . . If the owner or
operator chooses not to release the vehicle to
a third party, the vehicle shall be removed by
an agency-dispatched wrecker. A[n] inventory
will not be required if not impounded.
Where the police have taken a vehicle into police custody
as a law enforcement tow, and so requiring an inventory of the
vehicle pursuant to the two policies, the Inventory Policy explains
[t]he inventory will be completed by the law
enforcement officer ordering the tow and will
include the opening of closed containers and
the listing of their contents. The purpose of
the inventory is not to locate evidence of
criminal activity, but to protect the
owner[']s property, protect the agency from
subsequent claims of loss or stolen property,
and to protect law enforcement officers from
Among its standard procedures for conducting an inventory, the
Inventory Policy prescribes that "[t]he scope of such an
examination for personal property must be restricted solely to
those areas where the person would ordinarily be expected to store
or inadvertently leave his belongings, such as the floor, glove
compartment, door pockets, trunk, dashboard, and on, under, and
behind the seats."
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3. The Inventory Search and Search Warrant
At the impound facility, the Maine State Police K-9 unit
conducted a sniff of the exterior of the Escalade. The police dog
did not alert to any contraband. Lt. Cote, Dep. Bagley, and Dep.
McFarland then conducted an inventory search of the car. During
the inventory search, the officers found a wallet containing
Goodwin's driver's license in the backseat area, a cell phone in
the middle console, and a backpack in the front passenger area.
Inside the backpack, the officers found a loaded 9 mm handgun, a
plastic bag containing eight bundles of what the officers suspected
was heroin, and another plastic bag containing four chunks of a
white hard substance which the officers suspected was cocaine. At
that point, the officers agreed to stop the inventory search and
contact Agent Day so that the MDEA could obtain a search warrant
for the car. They left the evidence in the car, secured the car
with evidence tape, and locked it in a garage at the impound
On Sunday, May 21, 2017, two days after Sylvester had
been arrested, another MDEA special agent listened to a recorded
phone conversation made that day from the Hancock County Jail, in
which Sylvester was heard telling a woman "he had 10 grand in the
vehicle and it would be good if Hailee could get the vehicle out
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On Monday, May 22, 2017, Agent Day listened to the same
recorded conversation. That day, Agent Day applied for and
obtained a search warrant for the Escalade which authorized the
search of the entire car for drugs, firearms, evidence of drug
trafficking, and cell phones. In the affidavit submitted with the
warrant application, Agent Day described the circumstances of
Sylvester's arrest on the federal warrant, the seizure of the cash,
the negative K-9 sniff, the handgun and suspected drugs discovered
in the backpack in the front of the car during the inventory
search, and the recorded jail call in which Sylvester stated there
was ten grand in the car. The officers executing the search
warrant of the Escalade recovered a loaded 9 mm handgun,
ammunition, methamphetamine, heroin, cocaine, drug paraphernalia,
a cell phone, and suspected drug ledgers. They did not find the
money Sylvester mentioned in the jail call.
B. Procedural History
In July 2017, Sylvester was indicted on one count of
possession with intent to distribute cocaine, heroin, and five
grams or more of methamphetamine, in violation of 21 U.S.C.
§ 841(a)(1) and (b)(1)(B), and one count of possession of a firearm
in furtherance of a drug-trafficking crime, in violation of 18
U.S.C. § 924(c)(1)(A). In September 2017, Sylvester filed a motion
to suppress the evidence seized from the car he was driving at the
time he was arrested, challenging the lawfulness of the impound
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decision and the inventory search and the issuance of the search
The district court held argument based on the stipulated
facts on the motion to suppress on February 14, 2018. Defense
counsel argued that the officers were "towing [the car] for an
investigatory purpose" and were "not towing it under the community
caretaking function." Defense counsel also argued that the
officers' conversation captured by the dash-cam videos "is all
driven by, we want to search this vehicle, can we figure out a way
to lawfully do that," rather than "conceptualizing it as  this
[is] an impoundment and an inventory tow because we don't have
somebody else to drive it away." The court responded that "your
argument is subterfuge" and defense counsel stated "[i]t is a
subterfuge, and I think there is an investigatory purpose to taking
this vehicle from the side of the road to that tow yard." Defense
counsel argued that this investigatory purpose was in part
evidenced by the officers' failure to fully comply with the Impound
and Inventory Policies. But defense counsel did not ask the
district court to make a finding as to the reasons the officers
deviated from the policies by not notifying Sylvester that he could
2 The government did not contest Sylvester's standing to
challenge the impound and searches of the car based on an affidavit
he submitted stating that Goodwin authorized him to drive the
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contact a third party, including a preferred towing service, to
remove the car from the highway.
On February 15, 2018, the district court orally denied
Sylvester's motion to suppress. After concluding there was no
probable cause to search the car at the time Sylvester was
arrested, the district court held that the officers were justified
in impounding the car and inventorying its contents pursuant to
the community caretaking exception to the warrant requirement. It
found that the officers' cruisers' "video cams show that" "[t]his
was a stop and arrest on a busy highway in the breakdown lane."
The court also found "[t]here was no other driver on the scene"
and "the car needed to be moved" "because of its circumstances on
the highway," which provided "solid noninvestigatory reasons for
moving the car."
Turning to the alleged violations of the Impound and
Inventory Policies, the court concluded that the "deputies
violated the Hancock County policies by not trying to reach out to
[the defendant's girlfriend], give her the choice of taking the
vehicle if she could before they left the scene, or telling
Sylvester that he had first choice of what towing service to use,
but that they did not violate the policy in actually removing the
Nonetheless, the court made findings that the policies
authorized the impound in this situation where the driver had been
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arrested, the car was left dangerously along the side of the road,
and there was no one immediately available to remove the car. And
there's no evidence that  Sylvester asked
for an alternative to impoundment, [and] the
record doesn't make clear how it even could
have happened. The car belonged to the
girlfriend . . . who was not on the scene.
And on this record there is no evidence of a
viable alternative to getting someone to the
scene to remove the car before law enforcement
After reviewing First Circuit case law, the district
court found that "there's no subterfuge in the need to move the
car off the highway." It found that "there was an investigatory
motive for the impoundment[ which was] clear from listening to the
dash cam audio," but further concluded that the "co-existence of
investigatory and caretaking motives" "d[id] not irreparably taint
the impound" under First Circuit law.
Having held the initial impound of the car was valid,
the district court found that the subsequent inventory search was
conducted "according to established policy" and so concluded it
was also valid. The district court also held that regardless of
whether there was a policy violation during the inventory search,
there was probable cause to issue the search warrant for the car
even without the information learned from the inventory search
based on the federal arrest warrant, the circumstances of the
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arrest, and the jail call regarding the purported ten grand in the
Sylvester entered into a conditional plea agreement with
the government in October 2018, subject to his ability to appeal
the denial of his motion to suppress, and was sentenced in October
2019 to seventy-two months' imprisonment.3 This timely appeal from
his conviction followed.
Sylvester argues the district court's denial of his
motion to suppress was error. He argues that (1) the officers'
decision to impound the car was unlawful because it was done solely
for an investigatory purpose; (2) the subsequent inventory search
was unlawful because it was tainted by the initial unlawful impound
and the search warrant was not an independent source for the
evidence discovered during that inventory search; and (3) the
automobile exception to the warrant requirement did not justify
the search of the car.4 To be clear, Sylvester does not argue that
the initial stop of the car or his arrest were unlawful.
3 Sylvester also pleaded guilty to one count of conspiracy
to distribute controlled substances in a separate case and was
sentenced to thirty months' imprisonment to be served concurrently
with the sentence imposed in this case. That separate conviction
and sentence are not being challenged here.
4 The government conceded before the district court and on
appeal that the inventory search and search warrant were valid
only if the initial impound decision was also lawful. The
government also does not challenge the district court's
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In reviewing the denial of a motion to suppress, "[w]e
review factual findings for clear error and legal conclusion[s] de
novo." United States v. Coccia, 446 F.3d 233, 237 (1st Cir. 2006).
"[W]e will uphold a denial of a motion to suppress if any
reasonable view of the evidence supports it." Id. (quoting United
States v. Garner, 338 F.3d 78, 80 (1st Cir. 2003)). Where the
evidence of record is subject to different reasonable
interpretations, "the district court's choice between competing
inferences cannot be clearly erroneous." United States v. Hughes,
640 F.3d 428, 437 (1st Cir. 2011).
A. The Impound Decision
The district court found that the impoundment of the car
and its removal from busy Route 1A was a proper exercise of the
officers' community caretaking function. The community caretaking
function "is one of the various exceptions to the Fourth
Amendment's requirement that law enforcement officers have
probable cause and obtain a warrant before effecting a search or
seizing property." United States v. Rivera, 988 F.3d 579, 581
(1st Cir. 2021) (quoting Boudreau v. Lussier, 901 F.3d 65, 71 (1st
Cir. 2018)). "Under that exception, law enforcement officers, in
'their role as "community caretakers,"' may 'remove vehicles that
determination that there was not probable cause to search the car
under the automobile exception to the warrant requirement at the
time the car was stopped and Sylvester was arrested.
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impede traffic or threaten public safety and convenience' without
obtaining a warrant." Id. (quoting Boudreau, 901 F.3d at 72).
Our law has been clear on this point for years.
Pursuant to that exception, an impound decision is
constitutionally valid so long as it is reasonable under the
totality of the circumstances. See Coccia, 446 F.3d at 238-39;
United States v. Rodriguez-Morales, 929 F.2d 780, 785-86 (1st Cir.
1991). The impound decision must be justified by a legitimate,
non-investigatory purpose and cannot be "a mere subterfuge for
investigation, [but] the coexistence of investigatory and
caretaking motives will not invalidate the seizure." Coccia, 446
F.3d at 241 (quoting Rodriguez-Morales, 929 F.2d at 787); see also
Colorado v. Bertine, 479 U.S. 367, 372 (1987); United States v.
Del Rosario, 968 F.3d 123, 128-29 (1st Cir. 2020) ("To be clear,
we are not saying that an improper subjective motive renders the
community-caretaking exception inapplicable.");5 Boudreau, 901
F.3d at 72-73; Rodriguez-Morales, 929 F.2d at 787 ("[T]he
impoundment of the [car] in the exercise of the troopers' community
caretaking responsibilities was amply justified on objective
5 The Court in Del Rosario held that an impound decision
was invalid where there was no real objective justification for it
pursuant to the officers' community caretaking function, such that
the only conclusion was "that the seizure served no purpose other
than facilitating a warrantless investigatory search under the
guise of an impoundment inventory." 968 F.3d at 127-29.
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grounds. Hence, any speculation into the troopers' subjective
intent would be supererogatory.").
As to standardized procedures when impounding a vehicle,
this Court has already held that
it is inappropriate for the existence of (and
adherence to) standard procedures to be the
sine qua non of a reasonable impound
decision[.] . . .
. . . .
. . . [S]tandard protocols have
limited utility in circumscribing police
discretion in the impoundment context because
of the numerous and varied circumstances in
which impoundment decisions must be made.
Moreover, a police officer's discretion to
impound a car is sufficiently cabined by the
requirement that the decision to impound be
based, at least in part, on a reasonable
community caretaking concern and not
exclusively on "the suspicion of criminal
activity." Accordingly, the impoundment of
[the defendant]'s car did not violate the
Fourth Amendment merely because there was no
evidence that the impoundment was done
pursuant to pre-existing police protocols.
Coccia, 446 F.3d at 239 (emphasis added) (citations omitted)
(quoting Bertine, 479 U.S. at 375).
The district court, it is true, explicitly found that
the officers were motivated in part by an investigatory purpose.
But it went on to cabin that holding and also held that the officers
clearly had a legitimate and objectively reasonable noninvestigatory purpose. As it found, the car Sylvester was driving
when he was stopped and arrested was on the verge of a busy highway.
There were no other passengers nor anyone else immediately
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available to remove the car. Sylvester indeed never asserted that
the owner of the car was nearby or that anyone else could
immediately retrieve the car. Leaving the car on the shoulder of
a heavily trafficked highway was an obvious hazard to other
drivers, especially on a Friday night with darkness approaching.
Under these circumstances, the court did not err in
holding that the officers clearly had a legitimate community
caretaking justification for moving the car. See id. at 240
("Caselaw supports the view that where a driver is arrested and
there is no one immediately on hand to take possession, the
officials have a legitimate non-investigatory reason f[or]
impounding the car." (quoting Vega-Encarnación v. Babilonia, 344
F.3d 37, 41 (1st Cir. 2003))); Rodriguez-Morales, 929 F.2d at 785
(holding that the impound decision was reasonable where "leav[ing]
an automobile on the shoulder of a busy interstate highway" after
arresting the occupants would pose a threat to public safety).
The presence of both investigatory and community
caretaking motives does not render unlawful an objectively
reasonable decision to impound. Coccia, 446 F.3d at 241. And the
officers were not constitutionally required to "select the least
intrusive way of fulfilling their community caretaking
responsibilities." Rodriguez-Morales, 929 F.2d at 786; see also
Bertine, 479 U.S. at 373-74; Coccia, 446 F.3d at 240 n.7
(explaining that there is no Fourth Amendment requirement that
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officers "provide [the defendant] with an opportunity to arrange
for someone else to pick-up the car" before impounding and
inventorying it (citing Vega-Encarnación, 344 F.3d at 41)). The
officers' failure to fully comply with the Impound and Inventory
Policies with respect to the impoundment does not change this
result. See Coccia, 446 F.3d at 239.
The defendant does argue that the sole purpose of the
impound was investigatory, based on the fact that the officers
violated aspects of the Hancock County Impound and Inventory
Policies by not notifying him that he could request a third party
to immediately remove the car and thus created the need for
impoundment. See Coccia, 446 F.3d at 241 ("[T]here were legitimate
community caretaking justifications for impounding [the
defendant]'s car and there was no evidence that these
justifications were merely pretext for an investigatory search.").
But, Sylvester did not ask the district court to make a
specific finding about why the officers did not comply with those
aspects of the policies and none was made, thus precluding any
such argument from having merit, even if we were to assume that it
otherwise might.6 And that failure invokes the plain error
6 Because of the defendant's failure to request such a
finding, we have no need to address who has the burden of proving
pretext in this context. We note that two other circuits have
addressed the question in the same context or in similar contexts
and held the burden is on the defendant. See United States v.
Orozco, 858 F.3d 1204, 1213 (9th Cir. 2017); United States v.
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standard of review. It is self-evident there was no plain error.
See United States v. Takesian, 945 F.3d 553, 563 (1st Cir. 2019)
(explaining that "if an error pressed by the appellant turns on 'a
factual finding [he] neglected to ask the district court to make,
the error cannot be clear or obvious unless' he shows that 'the
desired factual finding is the only one rationally supported by
the record below'" (alteration in original) (quoting United States
v. Olivier-Diaz, 13 F.3d 1, 5 (1st Cir. 1993))).
B. The Inventory Search
We also hold that the district court did not err in
concluding that the subsequent inventory search of the car was
lawful. "The Fourth Amendment permits a warrantless inventory
search if the search is carried out pursuant to a standardized
policy," United States v. Richardson, 515 F.3d 74, 85 (1st Cir.
2008) (citing Florida v. Wells, 495 U.S. 1, 3-4 (1990)), and "on
the basis of something other than suspicion of evidence of criminal
activity," Bertine, 479 U.S. at 375. The district court did not
clearly err in finding that, once the car was impounded, the
inventory search of the car was conducted in accordance with the
Hancock County Inventory Policy. That policy states legitimate,
Maestas, 2 F.3d 1485, 1489 (10th Cir. 1993); see also United States
v. Magdirila, 962 F.3d 1152, 1157-58 (9th Cir. 2020) (applying
Orozco's burden allocation rule to the inventory context); United
States v. Johnson, 889 F.3d 1120, 1125-28 (9th Cir. 2018) (per
curiam) (applying Orozco's burden allocation rule to the impound
and inventory context).
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non-investigatory purposes. To the extent Sylvester argues that
the inventory search itself was invalid because that search was
also pretextual, that argument fails for the same reasons that his
other pretext argument does.
Outcome: The district court committed no error in denying
Sylvester's motion to suppress.