AI Case Brief
Generate an AI-powered case brief with:
📋Key Facts
⚖️Legal Issues
📚Court Holding
💡Reasoning
🎯Significance
Estimated cost: $0.10–$0.50 per brief, depending on opinion length and retries
Full Opinion
NOTICE: Summary decisions issued by the Appeals Court pursuant to M.A.C. Rule
23.0, as appearing in 97 Mass. App. Ct. 1017 (2020) (formerly known as rule 1:28,
as amended by 73 Mass. App. Ct. 1001 [2009]), are primarily directed to the parties
and, therefore, may not fully address the facts of the case or the panel's
decisional rationale. Moreover, such decisions are not circulated to the entire
court and, therefore, represent only the views of the panel that decided the case.
A summary decision pursuant to rule 23.0 or rule 1:28 issued after February 25,
2008, may be cited for its persuasive value but, because of the limitations noted
above, not as binding precedent. See Chace v. Curran, 71 Mass. App. Ct. 258, 260
n.4 (2008).
COMMONWEALTH OF MASSACHUSETTS
APPEALS COURT
22-P-956
COMMONWEALTH
vs.
TYRONE HOLLEY-HENDREN.
MEMORANDUM AND ORDER PURSUANT TO RULE 23.0
On April 27, 2022, the defendant, Tyrone John Holley-
Hendren, was found guilty of armed assault with intent to rob
and carrying a firearm without a license in connection with the
murder of Raymond Holloway-Creighton (the victim) who was shot
and killed by codefendant Tyler Sales (Sales) during the
commission of an attempted robbery. The defendant now appeals,
arguing that the trial judge erred or abused his discretion by:
(1) denying his motion to dismiss based on insufficient evidence
and denying both of his motions for a required finding of not
guilty; (2) admitting Facebook messages purportedly authored by
the defendant; (3) admitting the expert testimony of Officer
Timothy Trull (Officer Trull); and (4) denying the defendant's
motion to dismiss pursuant to Mass. R. Crim P. 36 (b), as
amended, 422 Mass. 1503 (1996), asserting a violation of his
right to a speedy trial. The defendant also argues he is
entitled to a new trial on the charge of carrying a firearm
without a license where the Commonwealth failed to present any
evidence of his lack of licensure. For the following reasons,
we affirm the defendant's conviction for armed assault with an
intent to rob but vacate and remand the defendant's firearm
conviction for further proceedings consistent with this
memorandum and order.
Background. We summarize the following relevant facts,
while reserving further facts for discussion below.
In the early morning of October 5, 2018, members of the
Boston police department responded to the area of 911
Massachusetts Avenue in response to a ShotSpotter activation for
a single gunshot fired at 3:30 A.M.1 When the police arrived,
they found the victim lying unconscious in the middle of the
street next to a motorized scooter.2 The victim suffered a
single gunshot wound to the back and was pronounced dead shortly
after he was transported to the Boston Medical Center.
1 ShotSpotter is an acoustic gunshot detection system that
uses GPS-enabled microphone sensors to geolocate detected
gunfire.
2 During the investigation it was later learned that the
victim was a delivery driver for GrubHub and Door Dash, third-
party food delivery services.
2
As a part of their investigation, police recovered
surveillance footage of the surrounding area showing the
defendant, Sales, and a second codefendant, Daniqua Douglas
Adedontun (Adedontun), riding motorized scooters throughout the
city from 1:57 A.M. to 4:46 A.M. on the morning of the shooting.
Adedontun rode on the back of the defendant's scooter, while
Sales rode alone. The surveillance footage showed that the
three perpetrators first encountered the victim near Magazine
Street, appearing to make repairs to his scooter. After fixing
his scooter, the victim drove away. The defendant, still with
Adedontun on the back of the scooter, followed the victim down
Chesterton Street and stopped his scooter directly to the right
of the victim at the end of the street, where it intersects with
Massachusetts Avenue. Next, codefendant Sales approached and
positioned his scooter behind the victim. The video then
depicted Sales raising his right arm, purportedly displaying a
firearm, directly towards the victim, who responded by getting
off his scooter. Moments later, the victim got back on his
scooter. At this point, the defendant began to dismount his
scooter on the side closest to the victim. The victim then
immediately attempted to turn left onto Massachusetts Avenue at
which point Sales fired at him, fatally striking him in the
back. The defendant, who had never fully dismounted, then
turned his scooter right onto Massachusetts Avenue, driving in
3
the opposite direction of the victim, and Sales followed on his
own scooter. Although the shooting occurred at 3:30 A.M.,
additional surveillance evidence showed the three codefendants
still riding their scooters together at 4:46 A.M. on Dorchester
Avenue.
As a result of the investigation, police interviewed the
defendant, who identified himself, Sales, and Adedontun in still
photographs taken from the surveillance footage.3 The defendant
told police that it was he and Adedontun that were riding
together on one scooter while Sales was riding alone. The
defendant admitted that earlier in the evening he had exchanged
Facebook messages with Sales regarding stealing scooters. The
police later obtained a search warrant to acquire these Facebook
records. As a result of the investigation, the defendant was
arrested.
Discussion. 1. Sufficiency of the evidence. The
defendant argues that the judge erred in denying his motion to
dismiss and denying his motions for a required finding of not
guilty because the Commonwealth failed to present sufficient
evidence to both the grand jury and at trial that the defendant
knew Sales was armed and shared Sales' intent to commit armed
assault with intent to rob. We disagree.
3 The defendant said he only knew Sales as "Tyler," but
police were able to identify Sales through a Facebook account.
4
"To sustain an indictment, the grand jury must be presented
with sufficient evidence to establish the identity of the
accused . . . and probable cause to arrest him for the crimes
charged" (quotation and citation omitted). Commonwealth v.
Rakes, 478 Mass. 22, 29 (2017). "'This standard . . . has been
employed primarily to strike down indictments in cases where a
grand jury has heard . . . no evidence whatever that would
support an inference of the defendant's' guilt." Id., quoting
Commonwealth v. Truong Vo Tam, 49 Mass. App. Ct. 31, 37 (2000).
We review the sufficiency of the evidence supporting an
indictment in the light most favorable to the
Commonwealth. Id.
Likewise, when reviewing claims of insufficient evidence
presented at trial, "we assess the evidence in the light most
favorable to the Commonwealth 'to determine whether any rational
trier of fact could have found each element of the crime beyond
a reasonable doubt.'" Commonwealth v. Baez, 494 Mass. 396, 400
(2024), quoting Commonwealth v. Robinson, 493 Mass. 303, 307
(2024). "The evidence may be direct or circumstantial, and we
draw all reasonable inferences in favor of the Commonwealth"
(citation omitted). Id.
To prove armed assault with intent to rob in a joint
venture, the Commonwealth is required to prove beyond a
reasonable doubt "that the defendant or a coventurer, or both,
5
while armed with a dangerous weapon, 'assault[ed] a person with
a specific or actual intent to rob the person assaulted.'"
Commonwealth v. Chesko, 486 Mass. 314, 320 (2020), quoting
Commonwealth v. Benitez, 464 Mass. 686, 694 n.12 (2013).
Because the offense of armed assault with intent to rob
"require[s] that the Commonwealth establish that the perpetrator
was armed, knowledge of a weapon is an element of the
Commonwealth's proof when a defendant is prosecuted on a theory
of joint venture" (quotation and citation omitted).
Commonwealth v. Garcia, 470 Mass. 24, 31 (2014). A joint
venturer's knowledge of a weapon may be inferred where "a
robbery is committed in a public place under circumstances where
it can be anticipated that a means must be found to persuade the
victim to surrender his property quickly and without
resistance." Commonwealth v. Colon, 52 Mass. App. Ct. 725, 728
(2001). Likewise, "[a] jury can infer that a defendant knew his
or her coventurer to be armed in cases where the victims'
resistance can reasonably be anticipated, as the defendant is
presumed to recognize the need for a means by which to overcome
that resistance." Rakes, 478 Mass. at 33.
a. Evidence before the grand jury. The evidence presented
to the grand jury was sufficient to establish the identity of
the defendant and probable cause to arrest him for the crime
charged. The evidence before the grand jury included the
6
testimony from Detective Phillip Bliss (Detective Bliss) that
the defendant originally became a suspect when he was identified
from the surveillance footage by three separate police officers.
Detective Bliss also summarized two recorded interviews during
which the defendant, after viewing the still photos from the
surveillance videos, identified himself as the person on the
scooter. The grand jury was also presented with the video
evidence of the defendant's fatal encounter with the victim, as
well as Facebook messages corroborated by video evidence from
that evening indicating that the defendant was planning on
stealing scooters. The Commonwealth also presented the grand
jury with the defendant's two recorded interviews. Accordingly,
the judge did not err in denying the defendant's motion to
dismiss the indictment. See Rakes, 478 Mass. at 29.
b. Evidence at trial. Viewed in the light most favorable
to the Commonwealth, the evidence adduced at trial was
sufficient to show that the defendant possessed the requisite
intent and knowledge to be convicted of armed assault with
intent to rob as a joint venturer. See Baez, 494 Mass. at 400.
First, as to the defendant's intent, the Commonwealth introduced
Facebook messages by the defendant expressing interest in
stealing scooters less than three hours before he and his
codefendants encountered the victim. The defendant, using the
7
account "Trappytoo Savage,"4 exchanged messages with the account
"Stupi Ty" and discussed the prospect of stealing various
scooters that Stupi Ty had purportedly identified on the street
just hours before the shooting. This conversation ended mere
minutes before the defendant met up with his codefendants.
Additionally, the surveillance footage showed that after
the defendant had been riding the streets of Boston for less
than two hours, he and his codefendants passed by the victim as
he was fixing his scooter before following him down Chesterton
Street, where the defendant pulled up beside the victim and
began to dismount his scooter on the side closest to the victim
before Sales fired his weapon. The defendant's expressed desire
to steal scooters, taken together with his actions leading up to
and during the shooting, reasonably demonstrate the requisite
intent to rob the victim.
Furthermore, the defendant's knowledge that Sales possessed
a firearm can be inferred from the totality of the
circumstances. First, the nature of the planned robbery made it
highly likely that a weapon would be involved. The victim was a
food delivery driver operating in a desolate, commercial area
around 3:30 A.M. It is reasonable to expect that someone
working alone late at night in such an environment would be
4 The defendant's arguments challenging the admission of
these messages are addressed below.
8
accustomed to managing risky situations on their own, making
them more likely to take precautions such as carrying a weapon
and staying vigilant, and less likely to simply comply with an
attempted robbery. Second, unlike a robbery of a store clerk or
pedestrian, a delivery driver on a moped has an immediate means
of escape, making it foreseeable that force or the threat of
force would be necessary to complete the crime. Third, the
coordinated manner in which the perpetrators approached the
victim supports a reasonable inference that they shared a common
understanding of the means and methods necessary to commit the
crime. While following the victim, the defendant and Adedontun
rode in front of Sales, while occasionally pausing to ensure
that Sales, who possessed the firearm, was not far behind. When
the victim stopped at the end of Chesterton Street, the
defendant pulled up next to the victim on his right side,
allowing Sales to position his scooter behind the victim. This
positioning allowed Sales to engage the victim with the firearm
while leaving the defendant and Adedontun in a position to take
the victim's scooter. Contrast Baez, 494 Mass. at 403-406
(finding knowledge of firearm could not be inferred where there
was no evidence defendant getaway driver saw or participated in
commission of shooting or shared assailants' intent).
9
Accordingly, the judge did not err in denying the
defendant's motions for a required finding at trial with respect
to his charge for armed assault with intent to rob.5
2. The Facebook messages. The defendant further argues
that the trial judge erred in admitting the Facebook messages
between Trappytoo Savage and Stupi Ty for the following reasons:
(1) the messages constitute hearsay and were unduly prejudicial;
(2) the Commonwealth failed to properly authenticate the
messages; and (3) no confirming circumstances indicated that
Sales or the defendant authored the messages. These arguments
are unavailing.
a. Hearsay. Rather than introduce the Facebook messages
for their truth, the Commonwealth introduced the messages for a
nonhearsay purpose, which was to offer evidence of the
defendant's state of mind and motive during the early morning of
October 5, 2018. Commonwealth v. Koney, 421 Mass. 295, 303
(1995). For example, while the messages discuss the location of
various scooters that Stupi Ty and Trappytoo Savage had
5 The defendant also suggests that the jury's verdict was an
improper compromise where the jury convicted the defendant of
armed assault with intent to rob but acquitted him of first-
degree felony murder. However, "speculation on reasons for the
jury's verdict . . . is fruitless. . . . [and a] finding of not
guilty can result from factors having nothing to do with actual
guilt." Commonwealth v. Elliffe, 47 Mass. App. Ct. 580, 585
(1999). Accordingly, this argument does not entitle the
defendant to relief.
10
identified to possibly steal, the Commonwealth did not introduce
the messages to prove that scooters were actually parked in the
locations referenced. Instead, the Commonwealth used the
messages to show the defendant's intent to steal scooters and
offer evidence of his motivation to rob the victim of his
scooter. Additionally, the probative value of these messages
was not substantially outweighed by the danger of unfair
prejudice, especially where the messages referenced chained
scooters and did not indicate that the defendant planned to
commit a violent crime. See Commonwealth v. McLeod, 39 Mass.
App. Ct. 461, 463-464 (1995). See also Mass. G. Evid. § 403
(2024).
b. Authentication and confirming circumstances. The
defendant further asserts that the trial judge improperly
admitted the Facebook messages where the Commonwealth presented
no evidence that the "Stupi Ty" account belonged to codefendant
Sales and no evidence that either the defendant or Sales
authored any of the messages.
"In the case of a digital communication that is relevant
only if authored by the defendant, a judge is required to
determine whether there is sufficient evidence to persuade a
reasonable trier of fact that it is more likely than not that
the defendant was the author of the communication."
Commonwealth v. Meola, 95 Mass. App. Ct. 303, 308 (2019). "[A]
11
judge making this threshold determination may consider
circumstantial evidence and look to 'confirming circumstances.'"
Id. at 311, quoting Commonwealth v. Purdy, 459 Mass. 442, 450
(2011). "We review a judge's preliminary determination of
conditional relevancy under Mass. G. Evid. § 104(b) under an
abuse of discretion standard." Id. at 309. "That standard
means that we will not disturb the judge's ruling absent a clear
error of either law or judgment in weighing the relevant
factors" (quotation and citation omitted). Id.
Here, the judge did not abuse his discretion in making a
preliminary determination that a jury could find by a
preponderance of the evidence that the defendant authored the
Facebook messages sent by Trappytoo Savage. See Meola, 95 Mass.
App. Ct. at 308. Specifically, the jury heard testimony from
Destinei Williams (Williams), the defendant's previous
girlfriend with whom he shares a child, that she communicated
with the defendant through Facebook on October 4, 5, and 6 of
2018, by messaging his account under the name "Trappytoo
Savage." Williams testified that she knew it was the defendant
due to the personal nature of their conversations. Furthermore,
around 1:50 A.M. on the day of the shooting, Trappytoo Savage
messaged Stupi Ty that he was "[c]oming down Morton," and
surveillance footage shows the defendant on his scooter in the
area of Morton Street approximately eight minutes later. Given
12
these confirming circumstances, there was ample evidence to
support the judge's determination to admit the messages. See
Meola, 95 Mass. App. Ct. at 311.
Additionally, the defendant asserts that the judge
improperly allowed the Commonwealth's motion for reconsideration
regarding the admission of the Facebook messages because the
Commonwealth's motion failed to show, pursuant to Mass. R. Crim.
P. 13 (a) (5), as appearing in 442 Mass. 1516 (2004), that
"substantial justice" required its allowance. This argument is
without merit. The judge did not abuse his discretion in
allowing the Commonwealth's motion for reconsideration regarding
the admission of the Facebook messages where the messages were
probative of the defendant's state of mind and there was
sufficient evidence that the defendant authored the messages.6
See Audubon Hill S. Condominium Ass'n v. Community Ass'n
Underwriters of Am., Inc., 82 Mass. App. Ct. 461, 470 (2012) ("a
motion for reconsideration calls upon the discretion of the
motion judge"); see also Commonwealth v. Lugo, 64 Mass. App. Ct.
12, 14 (2005) (finding rule 13 does not disturb judge's common
6 The Commonwealth did not attempt to show, and the judge
was not required to determine that Sales was the author of the
messages from the Stupi Ty account because the Commonwealth
introduced the messages to show that the defendant was engaged
in a joint venture with another person to steal scooters on the
night of the shooting. In this regard, the identity of the
defendant's coventurer was irrelevant.
13
law authority to "reconsider his own decisions during the
pendency of a case").
3. Officer Trull's testimony. The defendant also argues
that the trial judge abused his discretion in qualifying Officer
Trull as an expert on "bike life" and admitting his expert
testimony because it failed to meet the foundational
requirements for expert testimony in a criminal case. See
Commonwealth v. Barbosa, 457 Mass. 773, 783 (2010). This
argument is also unavailing.
Before expert testimony can be admitted in a criminal case
the Commonwealth must establish the following five foundational
requirements: "(1) that the expert testimony will assist the
trier of fact; (2) that the witness is qualified as an expert
in the relevant area of inquiry; (3) that the expert's opinion
is based on facts or data of a type reasonably relied on by
experts to form opinions in the relevant field; (4) that the
process or theory underlying the opinion is reliable; and
(5) that the process or theory is applied to the particular
facts of the case in a reliable manner" (citations omitted).
Barbosa, 457 Mass. at 783. The test for reliability is a
flexible one, and the trial judge's "gatekeeping inquiry must be
tied to the facts of a particular case" (quotations and citation
omitted). Kumho Tire Co. v. Carmichael, 526 U.S. 137, 150
(1999). "The admission of expert testimony will be reversed
14
only where it constitutes an abuse of discretion or other error
of law." Commonwealth v. Frangipane, 433 Mass. 527, 533
(2001).
Here, Officer Trull's expert testimony on "bike life," a
term describing, inter alia, the illegal operation and theft of
scooters, motorcycles, and off-highway vehicles (OHVs), was
based upon his experience assigned to the auto theft unit of the
Boston police department since 2014 where he has specifically
focused on bike life matters.7 To investigate suspects involved
in this subculture, Officer Trull testified that he monitors
suspected thieves on social media, tracks stolen vehicles and
vehicle parts through online postings, and has used "bait
scooters" to target thieves. He has also analyzed numerous
scooter thefts that have been caught on surveillance videos and
estimated that he has stopped approximately five hundred
individuals on scooters in the five years prior to his
testimony. Furthermore, Officer Trull assisted in drafting a
city ordinance, enacted in 2016, that allows law enforcement to
7 "Bike life" is a cultural phenomenon that arose in
Baltimore in 2010. The phenomenon is characterized by large
groups of people riding scooters, dirt bikes, motorcycles, and
OHVs through the city streets, often weaving in and out of
traffic and disobeying traffic laws. Bike life grew as
participants gained acclaim by posting their rides on social
media, and the movement spread throughout the northeast and into
Boston. As bike life gained popularity, so did scooter, dirt
bike, and OHV thefts, and a significant street market arose
where these vehicles and their parts are sold.
15
impound motorized recreational vehicles, such as scooters, dirt
bikes, and OHVs that are operated in public areas in a hazardous
manner, resulting in a reduced number of interactions between
law enforcement and riders. By engaging in these investigative
methods and legislative efforts, Officer Trull has become
familiar with the street value of stolen scooters, as well as
the methods employed by thieves to steal scooters and sell them.
For example, Officer Trull testified that these methods include
double riding, where two people ride on one scooter so the
passenger can drive away with the stolen scooter.
Given Officer Trull's extensive training and experience, as
well as his familiarity with the patterns and methods of
suspected scooter thieves, Officer Trull was qualified to
testify as an expert on bike life. See Frangipane, 433 Mass. at
533. Additionally, Officer Trull's testimony was helpful to the
trier of fact in evaluating the actions and motivations of the
defendant on October 5, 2018. See Barbosa, 457 Mass. at 783.
See also Commonwealth v. Miranda, 441 Mass. 783, 793 (2004).
Notably, the defendant was double riding when the group
approached the victim. Officer Trull's testimony also assisted
the jury in understanding the resell value of the victim's
scooter. Additionally, Officer Trull's testimony regarding his
investigative methods described a sufficiently reliable process
that is responsive to facts and data that he has gained as a
16
police officer. See Barbosa, supra at 783. Importantly, the
trial judge limited Officer Trull's testimony to his "general
experiences" and methodology as a police officer, and he did not
testify to his opinion of the facts of the case. Accordingly,
the trial judge did not abuse his discretion in admitting
Officer Trull's expert testimony. See Frangipane, 433 Mass. at
533.
4. Speedy trial. The defendant also urges that the trial
judge erred in denying his motion to dismiss pursuant to Mass.
R. Crim. P. 36 (b) in violation of his right to a speedy trial.
Rule 36 (b) (1) (C) states that " a defendant shall be tried
within twelve months after the return day in the court in which
the case is awaiting trial." Here, because the defendant's case
was awaiting trial in the Superior Court when the defendant
moved to dismiss, the "return date" under rule 36 must be
calculated from February 15, 2019, the day the defendant was
arraigned in Superior Court. See Commonwealth v. Polanco, 92
Mass. App. Ct. 764, 767 (2018). Significantly, while the period
between the defendant's arraignment and the start of his trial
exceeded the twelve months permitted by rule 36 by a total of
789 days, these days are all excludable from rule 36
17
calculations.8 For example, the Supreme Judicial Court's COVID-
19 Standing Orders deemed the time from March 13, 2020, to March
14, 2022, excludable from rule 36 calculations. See
Commonwealth v. Lougee, 485 Mass. 70, 77-80 (2020). This time
accounts for 731 days. Furthermore, the defendant concedes that
there are at least eighty-nine days of excluded time between
March 19, 2019, and February 13, 2020. Accordingly, the speedy
trial clock ran for less than twelve months, and the defendant's
rights under rule 36 were not violated.9
5. Firearm conviction pursuant to G. L. c. 269, § 10 (a).
The defendant argues, and the Commonwealth concedes, that he is
entitled to a new trial for his conviction of carrying of a
firearm without a license because the Commonwealth failed to
present any evidence of his lack of licensure in accordance with
the Supreme Judicial Court's decisions in Commonwealth v.
Guardado, 491 Mass. 666 (2023), and Commonwealth v. Guardado,
8 A period of 1,154 days elapsed from the date of the
defendant's arraignment on February 15, 2019, to the start of
the defendant's trial on April 13, 2022.
9 In the heading of his brief, the defendant states that he
was also deprived of a speedy trial under the Federal and State
constitutions. However, his subsequent argument and analysis
solely focus on his speedy trial claim under rule 36.
Therefore, because he fails to present an adequate argument with
respect to his constitutional speedy trial claim, we need not
address it on appeal. See Mass. R. A. P. 16 (a) (9) (A), as
appearing in 481 Mass. 1628 (2019). See also Lyons v. Secretary
of the Commonwealth, 490 Mass. 560, 593 n.42 (2022).
18
493 Mass. 1 (2023) (Guardado II). Indeed, because the defendant
was tried prior to June 23, 2022, and the Commonwealth failed to
present evidence of his lack of a license, we agree that the
defendant is entitled to a new trial for his firearm conviction.
See Guardado II, supra at 12.
6. Conclusion. For the reasons discussed above, we affirm
the judgment of conviction on the indictment charging the
defendant with armed assault with intent to rob. The judgment
of conviction on the indictment charging the defendant with
unlawfully carrying a firearm in violation of G. L. c. 269, § 10
(a), is vacated, the verdict is set aside, and the case is
remanded to the Superior Court for further proceedings
consistent with this decision.
So ordered.
By the Court (Desmond,
Walsh & Toone, JJ.10),
Clerk
Entered: February 7, 2025.
10 The panelists are listed in order of seniority.
19
Case Information
- Court
- Mass. App. Ct.
- Decision Date
- February 7, 2025
- Status
- Precedential