Commonwealth v. Emmanuel T. Bile, Jr.

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

23-P-630

COMMONWEALTH

vs.

EMMANUEL T. BILE, JR.

MEMORANDUM AND ORDER PURSUANT TO RULE 23.0

A Superior Court jury convicted the defendant of two counts

of aggravated rape.1 The defendant now appeals from the denial

of his motion for a new trial claiming, inter alia, that his

trial counsel was ineffective in failing to file a motion to

suppress text messages recovered from his cell phone.

Specifically, the defendant argues that the police, after

seizing his phone without his consent, unreasonably delayed for

forty days in obtaining a search warrant for his phone. We

1On direct appeal, the defendant claimed error in the
denial of his motion to suppress a recorded statement, jury
selection, several evidentiary rulings, jury instructions, the
prosecutor's closing argument, and the denial of his motion to
continue. In May 2020, a panel of this court affirmed his
convictions. See Commonwealth v. Bile, 97 Mass. App. Ct. 1120
(2020).
conclude that the defendant has demonstrated a likelihood that a

motion to suppress would have been successful because the

police's delay in obtaining a warrant was unreasonable given the

defendant's strong possessory interest in his phone. We also

conclude that there is a reasonable probability the verdict

would have been different had the text messages retrieved from

the defendant's cell phone been excluded from his trial.

Accordingly, we reverse and remand for a new trial.2

Background. We summarize the facts presented to the jury,

reserving additional facts for later discussion. The

convictions stemmed from allegations of nonconsensual sexual

conduct that occurred at a University of Massachusetts (UMass)

dormitory. On the evening of October 12, 2012, the victim, a

first-year student at UMass, became very intoxicated after

drinking alcohol with her friends in her dormitory. Between

midnight and 1 A.M., the defendant, Adam Liccardi, Justin King,

and Caleb Womack, who were acquaintances of the victim and did

not attend UMass, arrived uninvited at her dormitory.3 The four

2 Because we conclude that the defendant's ineffective
assistance of counsel claim requires reversal, we need not reach
the remaining claims raised on appeal.

3 All four men were indicted for raping the victim.
Following separate jury trials, Adam Liccardi was convicted of
two counts of aggravated rape and one count of rape, and Justin
King was convicted of three counts of aggravated rape. Caleb

2
men partied in the victim's room with the victim and two of her

friends who lived on the same floor of the dormitory. At one

point, the victim became so intoxicated that she could not stand

up without assistance. In response to her condition, the

victim's friends assisted the victim getting into her bed and

told the defendant, Liccardi, King, and Womack that it was time

to leave the victim's room. Despite this directive, Liccardi

and King remained in the victim's room, and the defendant, along

with Womack, returned to her room soon after the victim's

friends had departed. The four men then engaged in sexual acts

with the victim while she was in and out of consciousness. The

defendant later admitted that he penetrated the victim's vagina

with his penis.4 When the victim began to cry loudly, the

defendant, King, and Womack stopped and left her room. Liccardi

remained with her and sought to console her before sexually

assaulting her again.

The next morning, on October 13, the victim, who was

visibly upset and bruised, told one of the friends who had

Womack pleaded guilty to reduced charges of rape and indecent
assault and battery.

4 The defendant, during his interview with the police On
October 17, 2012, admitted that he penetrated the victim's
vagina with both his penis and finger, and anally with his
finger. At trial, the defendant testified that he only
penetrated the victim's vagina.

3
assisted her the night before that she had been repeatedly raped

by the four men. On the morning of October 15, 2012, the victim

reported the assault to UMass police. The victim allowed the

police to view her phone after telling them that she had

communicated with the defendant through text messages in the

days following the rape. The police then took photographs of

text messages displayed on the victim's phone, between the

victim and the defendant. On the same day, the victim underwent

a sexual assault nurse examination at a nearby hospital. The

subsequent examination of sperm samples from an external genital

swab and vaginal swab taken from the victim showed a match with

the defendant's DNA.

On October 17, the UMass police interviewed the defendant.

During the interview, the defendant stated he had what he

believed to be consensual sex with the victim. He described how

he and the three other men "took turns" engaging in sexual acts

with the victim. The defendant claimed it was consensual but

admitted the incident was out of character for the victim. He

described her condition as being "drunk," but not so intoxicated

that she could not consent to the encounter. The defendant

admitted that he responded to the victim's text messages to him

the following day. He also admitted that he sent text messages

to King, Liccardi, and Womack concerning the victim's allegation

4
that they had sexually abused her. When the police asked the

defendant to see his phone, the defendant declined to show it to

them. However, at the end of the interview, the police seized

the defendant's phone without either a warrant or his consent.

On November 26, forty days later, the police applied for and

received a search warrant for the cell phone.

The search of the defendant's phone yielded text messages

between the defendant and the victim,5 and between the defendant

and his codefendants; ninety-eight of these messages were

admitted at trial. For example, on the morning after the

alleged rape, the victim sent a text message to the defendant,

"You fucking brought them and didn't stop it. I'm fucking

bleeding internally." The defendant responded by messaging the

victim, "I'm sorry. I shouldn't have let that happen" and "I

failed you as a good friend and I'm sorry."

In another text message to the defendant, the victim

demanded five hundred dollars from the defendant and the other

men, warning the defendant that she would "tak[e] you all to

court" if they did not pay her. The defendant responded to the

victim's demand for five hundred dollars by texting, "[I']ll

talk to everyone and get [you] the money." Approximately one

As noted supra, the victim had previously shared the texts
5

between her and the defendant with police.

5
hour later, the defendant sent a text message to King saying,

"Call me after work we have to talk." The next day, on October

14, the defendant sent a text message to Womack asking him to

meet in person. And, on October 15, the defendant sent a text

message to Liccardi and stating that they needed to talk about

"what [the victim] wants to do to us." When Liccardi asked if

they were "beat," the defendant replied, "We aren't beat . . .

she tried blackmailing us so that's our defense."

On October 15, King sent a text message to the defendant

and asked, "What if they have cameras in the hallways?" and the

defendant replied, "Let's hope they don't." During the

following two days, the defendant and King exchanged text

messages about trying to convince Liccardi and Womack to pay the

victim the money she requested to avoid criminal charges. The

defendant communicated that they needed to do something to take

care of "the [victim] situation." In one exchange, the

defendant agreed with King that they were "fucked" if the victim

took them to court, that they "all" had to talk to get "rid of

this problem as fast as possible," and that they should pay the

victim whatever money she demanded.

The defendant's trial counsel did not move to suppress

these text communications as fruits of an unlawful search and

seizure of the defendant's phone.

6
Discussion. When a defendant moves for a new trial based

on ineffective assistance of counsel, the defendant must

demonstrate (1) performance on the part of counsel falling

measurably below that of an ordinary, fallible attorney, that

(2) effectively deprived the defendant of a substantial ground

of defense. See Commonwealth v. Saferian, 366 Mass. 89, 96

(1974). When a defendant asserts a claim of ineffective

assistance based on counsel's failure to file a motion to

suppress, "the defendant has to demonstrate a likelihood that

the motion to suppress would have been successful."

Commonwealth v. Comita, 441 Mass. 86, 91 (2004). In addition,

the defendant must show prejudice, that is, "a 'reasonable

probability' that, 'but for counsel's unprofessional errors, the

result of the proceeding would have been different.'"

Commonwealth v. Mahar, 442 Mass. 11, 15 (2004), quoting

Strickland v. Washington, 466 U.S. 668, 694 (1984). See Comita,

supra at 90, quoting Kimmelman v. Morrison, 477 U.S. 365, 375

(1986). We review the denial of a motion for new trial for an

abuse of discretion or any other error of law. See Commonwealth

v. Lane, 462 Mass. 591, 597 (2012).

1. Likelihood of suppression motion's success. Police may

retain an item seized without a warrant for "the relatively

short period of time needed . . . to obtain a search warrant,"

7
but must release the item if a warrant is not obtained within

that period (citation omitted). Commonwealth v. Gentile, 437

Mass. 569, 573, 575 (2002). For this reason, once a warrantless

seizure has been executed, the police "must make it a priority

to secure a search warrant that complies with the Fourth

Amendment." Commonwealth v. White, 475 Mass. 583, 593 (2016),

quoting United States v. Burgard, 675 F.3d 1029, 1035 (7th

Cir.), cert. denied, 568 U.S. 852 (2012). If the police fail to

do so, the seizure, even if "reasonable at its inception because

based upon probable cause[,] may become unreasonable as a result

of its duration." Segura v. United States, 468 U.S. 796, 812

(1984).

"[T]here is no bright-line rule that demarcates when a

delay is unreasonable." Commonwealth v. Cruzado, 480 Mass. 275,

283 (2018). Rather, the inquiry involves "balanc[ing] the

nature and quality of the intrusion on the individual's Fourth

Amendment interests against the importance of the governmental

interests alleged to justify the intrusion" (citation omitted).

White, 475 Mass. at 593-594. "'[C]ourts have identified several

factors highly relevant to this inquiry,' among them, and of

particular importance here, whether police acted 'diligen[tly]

in obtaining the warrant.'" Id. at 594, quoting United States

v. Laist, 702 F.3d 608, 613-614 (11th Cir. 2012).

8
A reasonable delay in obtaining a search warrant may be

justified by a strong government interest. See Cruzado, 480

Mass. at 284 (Commonwealth's interest in defendant's phone was

strong and justified ten-day delay in seeking search warrant

where "police had probable cause to believe that evidence

critical to a recent murder was present on the cell phone").

See also Illinois v. McArthur, 531 U.S. 326, 332–333 (2001)

(reasonable to prevent suspect from entering home for two hours

while police obtained warrant); United States v. Van Leeuwen,

397 U.S. 249, 252–253 (1970) (reasonable for police to seize

package for twenty-nine hours while seeking warrant).

In assessing the reasonableness of the delay, though, a

strong government interest in the property may be outweighed by

other factors such as lack of diligence in obtaining a warrant,

and a defendant's strong possessory interest in the property.

See White, 475 Mass. at 590, 595. See also United States v.

Pratt, 915 F.3d 266, 271-272 (4th Cir. 2019). The court's

reasoning in Pratt is instructive to the instant case. In that

case, the court held that a thirty-one day delay in obtaining a

warrant for a defendant's cell phone was unreasonable even after

determining that the government had a strong evidentiary

interest in the phone because the defendant, who was being

investigated for running a prostitution ring, admitted it

9
contained nude pictures of an underage sex worker. Id. at 270-

272. The court concluded that the government's strong interest

in the phone did not outweigh the defendant's "undiminished

possessory interest" because "[h]e didn't consent to its seizure

or voluntarily share the phone's contents." Id. at 272.

Further, the defendant's phone did not have evidentiary value

independent of its contents that would justify its indefinite

seizure. Id. at 273. Cf. Commonwealth v. Arthur, 94 Mass. App.

Ct. 161, 165 (2018) (cell phones' located in separate cars at

crime scene of coordinated shooting provided independent

evidentiary value on question of joint venture). Given the

defendant's "undiminished interest" in the phone, the court

reasoned that by not taking steps to obtain a warrant for

thirty-one days, the government had not acted with diligence and

the delay was unreasonable. See Pratt, 915 F.3d at 273.

Here, like in Pratt, the government had a strong interest

in the defendant's phone because of the evidence that it

contained -- incriminatory text communications with the victim

and codefendants. See Pratt, 915 F.3d at 270-271; see also

Cruzado, 480 Mass. at 284 (strong government interest justified

ten-day delay in seeking warrant where "police had probable

cause to believe that evidence critical to a recent murder was

present on the cell phone"). However, the defendant's

10
possessory interest in his phone was also similarly strong to

that in Pratt considering that he did not consent to its

seizure. See Pratt, supra at 272-273. Contrast Cruzado, supra

at 283-284 (minimal possessory interest in cell phone where

defendant disclaimed it belonged to him). Moreover, the phone

was not relevant independent of its contents. See Pratt, supra

at 273. Therefore, whether law enforcement was diligent in

obtaining the warrant becomes critical. See White, 475 Mass. at

594-595.

The Commonwealth argues the forty-day delay did not result

from a lack of diligence. It argues the complexity of the

investigation into the defendant and his codefendants, when

accounting for facts that the police were obtaining other

warrants and that multiple law enforcement agencies were

involved, justified the delay. We disagree. While "the nature

and complexity of the investigation" are factors in discerning

the reasonableness of a delay, Laist, 702 F.3d at 614, "[t]he

relevant inquiry . . . does not concern the detectives' general

diligence in performing their duties, but, rather, whether they

acted 'diligen[tly] in obtaining the warrant.'" White, 475

Mass. at 594, quoting Laist, supra.

Here, the UMass police did not act diligently in obtaining

a warrant once they seized the defendant's phone without his

11
consent. For instance, there is no indication from the record

that the police "put the ball in motion" soon after seizing the

phone by drafting or otherwise preparing the warrant affidavit.

Cf. Laist, 702 F.3d at 610-611 (twenty-five day delay reasonable

where law enforcement demonstrated diligence by beginning to

prepare warrant affidavit eight days after seizure and exchanged

drafts of affidavit with prosecution thereafter). In contrast,

the police appeared to be diligent in other matters involving

this investigation, as they applied for and obtained eight other

warrants two days after the defendant's phone was seized.6

However, the police failed to prioritize obtaining a warrant for

the defendant's seized cell phone. See White, 475 Mass. at 594-

595 (sixty-eight day delay in obtaining search warrant

unreasonable because police required to act diligently in

obtaining warrant and "it does not appear that they did so,

having instead focused on . . . applying for and executing five

other search warrants related to this case). See also Burgard,

675 F.3d at 1035 (prioritizing warrant "entail[s] diligent work

to present a warrant application to the judicial officer at the

earliest reasonable time").

6 UMass police seized the defendant's phone on October 17,
2012. On October 19, 2012, the UMass police applied for and
obtained four search warrants (for the "bodies" of the
defendant, Liccardi, Womack, and King) and four arrest warrants
(for the defendant, Liccardi, Womack, and King).

12
Furthermore, the search warrant affidavit for the

defendant's phone did not establish there was anything complex

about drafting a warrant for digital forensic examination that

would explain the delay here. See United States v. Mitchell,

565 F.3d 1347, 1351 (11th Cir. 2009) (court found twenty-one day

delay in obtaining search warrant unreasonable noting affidavit

did not contend officer preparing warrant was unfamiliar with

background of child pornography investigation or that he lacked

sufficient knowledge to prepare affidavit). Nor does the record

reflect that the cell phone data extraction process was

particularly unfamiliar or difficult for the State police such

that additional preparation by the UMass police would be

required. In fact, the warrant appears to contain "boilerplate"

language concerning the phone's capacity to store data as well

as the extraction of such data.7 Once the UMass police obtained

the search warrant, a State police detective, who had previously

performed "at least [fifty]" cell phone data extractions using

the same software tool as he used here, extracted the cell phone

data from the defendant's phone in less than two days.

7 The affidavit was limited to the following language
pertaining to extraction of data:

"I know that these various forms of data that are stored
within cellular phones can be extracted from the phone.
Extraction involves police making a copy of the data within
the cellular phone."

13
Because the defendant maintained a strong possessory

interest in his phone, the police had an obligation to either

obtain a warrant without unreasonable delay or to return the

property; they did neither. After balancing the nature of the

intrusion to the defendant's Fourth Amendment interest in his

cell phone with the Commonwealth's interest in accessing the

phone's contents, accounting for the Commonwealth's lack of

diligence in obtaining a search warrant, on the record before

us, we conclude the forty day delay here was unreasonable. See

White, 475 Mass. at 593-594. Thus, the defendant has shown a

likelihood that a motion to suppress evidence recovered from his

phone would have been successful.

2. Reasonable probability of different verdict. To

prevail on his motion for new trial based on ineffective

assistance of counsel, the defendant must also show a reasonable

probability that the verdict would have been different without

the admission of the text messages that would have been excluded

but for counsel's incompetence. See Comita, 441 Mass. at 91;

Commonwealth v. Pena, 31 Mass. App. Ct. 201, 205 (1991). Such a

probability exists here due to the highly prejudicial nature of

the text messages that the jury never should have considered.

Specifically, the defendant's cell phone contained messages with

all three of his codefendants concerning the nature of their

14
encounter with the victim that supported the Commonwealth's

theory of the case and directly contradicted both of the

defendant's primary defenses at trial -- first, that he did not

take part in a joint venture to rape the victim,8 and second,

that his encounter with the victim was consensual. The

Commonwealth relied significantly on the text messages to show

the defendant's consciousness of guilt,9 as well as to establish

his willful participation in the joint venture to rape the

victim. Notably, the Commonwealth's theory of joint venture was

not limited to the element of aggravation, but also was the

basis for the underlying elements of the rape charges.10

8 The judge's final instructions to the jury concerning the
Commonwealth's theory of joint venture included: "You have
heard evidence of statements made in text messages purported to
have been sent by Justin King, Caleb Womack, and Adam Liccardi.
The Commonwealth offered that evidence against the defendant
Bile to show his alleged participation in a joint venture."

9 The Commonwealth articulated its consciousness of guilt
rationale for admission of the text messages in its motion to
"Admit Defendant's Text Messages with Co-Defendants Post-
Incident Reflecting Consciousness of Guilt"; the trial judge
allowed the motion.

10The prosecutor expressly indicated this theory when, in
response to the judge's request for clarity as to her proposed
jury instruction concerning joint venture, responded: "I think
once [the jury] ha[s] found a joint venture, that there was a
joint venture, it is both, justifies a finding of culpability on
the three counts [of rape] and it also justifies a finding of
the third element for aggravated rape." The judge instructed
accordingly with no objection from the defendant.

15
Consistent with its theory of proof, and to cast doubt on

the defendant's defenses, the Commonwealth emphasized the

defendant's text messages in its opening and closing statements,

and during its cross-examination of the defendant. For example,

in the Commonwealth's opening statement, the prosecutor offered

the text messages from the defendant to his codefendants to

demonstrate they had worked in concert, stating, "you'll see

those text messages between them . . . and you will see that

they wanted to take care of the [victim] situation, this problem

as fast as possible, and they agreed to pool the money to pay

her." The Commonwealth also relied on the text messages to show

the defendant's consciousness of guilt, telling the jury, "[you]

will also see [the codefendants] had several concerns,"

including "the possibility of surveillance cameras in the dorm."

During the Commonwealth's cross-examination of the

defendant, the prosecutor relied on his text messages to the

codefendants to provide damaging context to the statements he

made to the victim on the morning after the alleged rape

occurred. The prosecutor also confronted the defendant with the

text messages amongst him and his codefendants planning their

defense that the victim was blackmailing them, and in addition,

admitted that they would be "fucked" if the victim took them to

court.

16
The prosecutor, in her closing argument, again used the

defendant's text messages to demonstrate that he was part of a

joint venture to rape the victim, first by stating "look to his

own text messages" to show "[h]e's not the good guy and [his

codefendants] the bad guys. He's just as much a part of this

group . . . a part of what happened." The prosecutor concluded

her argument in part by emphasizing how the text messages proved

the defendant's participation in the joint venture as well as

his acknowledgment of guilt.11

The Commonwealth's reliance on the text message evidence

throughout the trial demonstrates its belief that this evidence

was highly persuasive in establishing the defendant's guilt.

Considering that the incriminating text messages related

directly to the elements of the offense, we conclude that there

is a reasonable probability the verdict may have been different

11The jury could have reasonably viewed the text messages
as far more damaging that the defendant's admission in which he
minimized both his shared intent with his codefendants
concerning their trip to UMass as well as the acts he committed
against the victim. For instance, the prosecutor argued:

"And if you need more evidence [that the defendant is as
culpable as his codefendants] . . . look to his own text
messages. Text messages he testified about yesterday,
you'll have in writing. You can read those. He went there
with the plan to fuck dem bitches, excuse my language. To
put it in. To put it in the butt. That's what he's saying
twenty-four hours before arrival there at UMass."

17
if such evidence had been excluded from the trial. See

Commonwealth v. Alvarez, 433 Mass. 93, 104 (2000) ("Where, as

here, the very matter as to which defense counsel has been

ineffective becomes one of the linchpins of the prosecutor's

closing, the defendant has met [their] burden of showing

prejudice"); Commonwealth v. Segovia, 53 Mass. App. Ct. 184, 193

(2001) (ineffective assistance where counsel's failure to move

to suppress evidence "opened the door to numerous negative

inferences against the defendant, all of which were explored in

the prosecutor's opening and closing"). A motion to suppress

the significant, illegally obtained contents of the defendant's

phone would have represented "better work [that] might have

accomplished something material for the defense." Commonwealth

v. DiGeronimo, 38 Mass. App. Ct. 714, 730 (1995), quoting

Commonwealth v. Satterfield, 373 Mass. 109, 115 (1977).

18
Conclusion. We reverse the order denying the defendant's

motion for a new trial. The defendant's convictions are

vacated, the verdicts are set aside, and the matter is remanded

to the Superior Court for a new trial.

So ordered.

By the Court (Massing, Hand &
Smyth, JJ.12),

Clerk

Entered: April 16, 2025.

12 The panelists are listed in order of seniority.

19