Commonwealth v. Milan

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25-P-720 Appeals Court

COMMONWEALTH vs. MICHAEL T. MILAN.

No. 25-P-720.

Essex. March 16, 2026. – May 14, 2026.

Present: Meade, Hodgens, & Allen, JJ.

Obscenity, Dissemination of matter harmful to minor. Social
Media. Constitutional Law, Indictment. Waiver. Practice,
Criminal, Instructions to jury, Waiver, Loss of evidence by
prosecution. Evidence, Best and secondary.

Indictments found and returned in the Superior Court
Department on December 15, 2021.

The cases were tried before Brent A. Tingle, J.

David M. Osborne for the defendant.
Kristen W. Jiang, Assistant District Attorney, for the
Commonwealth.

MEADE, J. After a jury trial, the defendant was convicted

of six counts of disseminating harmful material to a minor. On

appeal, he claims that defects in his indictments require his

convictions to be reversed; the indictments were improperly

amended; the judge abused his discretion in not giving a
2

requested jury instruction; and the judge abused his discretion

by fashioning an inadequate remedy for the Commonwealth's loss

or destruction of potentially exculpatory evidence. We affirm.

Background. In 2019, twenty-two year old Ipswich police

Officer Kelly Phelan, acting in an undercover capacity, created

a social media account in which she posed as a fourteen year old

girl, "Crayon Mia." Phelan joined an online social media group

and posted a message. While she did not remember the exact

wording of the message, it was Phelan's practice to state, "I'm

Mia. I'm 14 years old. I'm from Massachusetts. Anyone want to

chat?" She did not preserve this initial message or her

associated profile photograph. Phelan stated that it was not

her "practice" to do so at the time. She feared that if she

"burn[ed] the undercover account," which took some time to

establish as authentic, she would be unable to use it in future

investigations. Phelan admitted that this was an "investigatory

mistake" as she had graduated from the police academy only a few

months prior to this investigation.

Several hours after her initial post, at 1:13 A.M., Phelan

received a private message from the thirty-three year old

defendant, who used the profile name "Magic Mike." Over the

course of two months, the defendant exchanged frequent messages

with "Crayon Mia." In these messages, Phelan repeatedly told
3

the defendant that she was fourteen years old, had never had a

boyfriend, and that she was sexually inexperienced.

Over time, the defendant's messages became increasingly

sexual in nature. On five separate occasions, the defendant

sent Phelan photographs of his erect penis, and on one occasion

he sent a photograph of a naked woman. He also asked Phelan to

send intimate photographs of herself and described a variety of

sexual acts he wished to do with her. The defendant noted that

he did not live far away, suggested that they could meet, and he

offered to "be [her] practice."

At trial, the defendant did not dispute that he had

distributed harmful matter in his online communications with

Phelan, but rather argued that he did not believe that "Crayon

Mia" was actually a minor. Relative to this contested issue,

the Commonwealth provided the jury with numerous screen shots of

their conversations in which "Crayon Mia" identifies herself as

being fourteen years old and mentions her sexual inexperience.

Two of the screen shots included photographs of Phelan.

In his defense, the defendant testified that he believed

that "Crayon Mia" was an adult engaging in sexual role play,

i.e., "someone playing the part of a 14-year-old." In support,

the defendant claimed the platform users had to certify that

they were eighteen years old or older to be admitted to the

online social media group, which was known for role playing. In
4

addition, in his view, the photographs on Phelan's profile

depicted not a minor, but a woman in her early twenties. He

also testified that "Crayon Mia" was sexually suggestive from

the beginning of their communications and told him, "I'll do

anything you want."

The defendant also highlighted Phelan's failure to preserve

her profile photograph and the initial message she posted. He

later argued to the jury that Phelan had intentionally destroyed

those items because they undercut the Commonwealth's theory of

the case and supported the defendant's claim that he believed he

was role playing with an adult.

1. The indictments. Each indictment charged that the

defendant "did disseminate harmful matter to a minor, knowing

said matter to be harmful; or did possess such matter with the

intent to disseminate it to a minor."1 This tracked the language

found in an older version of G. L. c. 272, § 28, as appearing in

St. 1982, c. 603, § 2. In 2011, the statute was amended to add

the requirement that the defendant "purposely disseminates to a

1 A "matter is harmful to minors if it is obscene or, if
taken as a whole, it (1) describes or represents nudity, sexual
conduct or sexual excitement, so as to appeal predominantly to
the prurient interest of minors; (2) is patently contrary to
prevailing standards of adults in the county where the offense
was committed as to suitable material for such minors; and (3)
lacks serious literary, artistic, political or scientific value
for minors." G. L. c. 272, § 31.
5

person he knows or believes to be a minor any matter harmful to

minors." See G. L. c. 272, § 28, as amended by St. 2011, c. 9,

§ 19. For the first time on appeal, the defendant claims that

because his indictments did not contain the knowledge or belief

element, relative to dissemination to a minor, and that his

charged conduct postdated 2011, his indictments failed to charge

a crime. We disagree.2

General Laws c. 277, § 47A, provides, in pertinent part:

"In a criminal case, any defense or objection based upon
defects in the institution of the prosecution or in the
complaint or indictment, other than a failure to show
jurisdiction in the court or to charge an offense, shall
only be raised prior to trial and only by a motion in
conformity with the requirements of the Massachusetts Rules
of Criminal Procedure. The failure to raise any such
defense or objection by motion prior to trial shall
constitute a waiver thereof, but a judge or special
magistrate may, for cause shown, grant relief from such
waiver" (emphasis added).

To avoid waiver, the defendant first claims that his

challenge is based on "a failure to show jurisdiction in the

court or to charge an offense," i.e., the claim relates to the

Superior Court's subject matter jurisdiction. However, this is

2 The defendant claims the prior version of the statute is
unconstitutional. This is incorrect. To the extent a Federal
District Court judge held otherwise, we are not bound by that
decision. See Commonwealth v. Pon, 469 Mass. 296, 308 (2014).
In any event, in Commonwealth v. Jones, 471 Mass. 138, 144-146
(2015), the Supreme Judicial Court determined that the prior
version of the statute contained an implied element of
knowledge, even if not explicitly stated therein, and upheld its
constitutionality.
6

incorrect. "Subject matter jurisdiction concerns the power of

the court to entertain a particular category of case."

Commonwealth v. Doughty, 491 Mass. 788, 805 (2023). "The

Superior Court has 'original jurisdiction of all crimes.'" Id.

at 805-806, quoting G. L. c. 212, § 6. "[A] defect in an

indictment is not a question concerning the subject matter

jurisdiction of the court." Doughty, supra at 806.3 Because the

defendant did not raise this issue prior to trial, and it is not

based on subject matter jurisdiction, it cannot be a basis to

avoid statutory waiver. See Commonwealth v. Lamont L., 438

Mass. 842, 845 (2003); Commonwealth v. Hrycenko, 417 Mass. 309,

312 (1994).

However, the second exception to waiver under G. L. c. 277,

§ 47A, i.e., a claim that his indictments do not charge crimes,

does apply to the defendant. Although not waived, the claim is

without merit. "An indictment will not be dismissed 'if the

offense is charged with sufficient clarity to show a violation

of law and to permit the defendant to know the nature of the

accusation against him.'" Commonwealth v. Sullivan, 82 Mass.

3 The defendant claims that this case is controlled by
Commonwealth v. Palladino, 358 Mass. 28, 31 (1970), as well as
others to which he cites in support of his jurisdiction claim,
see, e.g., Commonwealth v. Garrett, 473 Mass. 257, 264 (2015);
Commonwealth v. Senior, 454 Mass. 12, 14 (2009); Commonwealth v.
Andler, 247 Mass. 580, 581-582 (1924). However, the contrary
conclusions in all of these cases have been disavowed by
Doughty, 491 Mass. at 805-806 & n.26.
7

App. Ct. 293, 295–296 (2012), quoting Commonwealth v. Fernandes,

430 Mass. 517, 520 (1999), cert. denied sub nom. Martinez v.

Massachusetts, 530 U.S. 1281 (2000). "It is not necessary for

the Commonwealth to set forth in the . . . indictment every

element of the crime to withstand a motion to dismiss" (citation

omitted). Sullivan, supra at 296.

Here, pursuant to G. L. c. 272, § 28, as set forth in the

indictments, the defendant had adequate notice that he was

charged with dissemination of harmful materials to a minor.

Even if the charging language in the indictments did not exactly

track the language added by the Legislature in 2011, each

indictment, when read as a whole, "identifie[d] that the offense

charged is a violation of [G. L. c. 272, § 28], which is a

crime." Doughty, 491 Mass. at 806. See G. L. c. 277, § 34.

Finally, even under the pre-2011 version of § 28, a defendant

could properly be charged with dissemination in cases where the

recipient was actually an adult posing as a minor. See

Commonwealth v. Ericson, 85 Mass. App. Ct. 326, 336 n.13 (2014).

The defendant also claims his convictions must be vacated

because he was convicted of crimes not charged by the grand

jury. Specifically, the defendant claims that the prosecutor's

opening statement constructively amended his indictments, over
8

his objection,4 by stating that the evidence would show that the

defendant "sent explicit messages, not to a minor, but to an

undercover police officer posing as a fourteen-year-old." We

disagree.

As stated above, the indictments properly charged the crime

of dissemination under G. L. c. 272, § 28, under which the

defendant could have been prosecuted even prior to the

Legislature clarifying in 2011 that the defendant must know or

believe that the intended recipient is a minor. See

Commonwealth v. Jones, 471 Mass. 138, 144-146 (2015) (prior

version of § 28 contained implied element of knowledge [or

belief] that recipient was minor). Accordingly, the prosecutor,

in laying out the expected evidence, did not amend the

indictments by explicitly stating that which the Supreme

Judicial Court had held was fairly implied in § 28. In other

words, the "knows or believes to be a minor" language was not

essential to the description of the crime charged, nor did it

add an essential element to the crime. Contrast Commonwealth v.

Ruidiaz, 65 Mass. App. Ct. 462, 463-464 (2006). For these

reasons, the judge properly denied the defendant's motion for a

required finding of not guilty.

4 At the conclusion of the prosecutor's opening statement,
the defendant moved for a required finding of not guilty based
on this claim.
9

2. Jury instruction. The defendant also claims that the

judge was required to give his requested jury instruction on the

definition of "belief," which would have informed the jury that:

"[T]he Commonwealth must prove beyond a reasonable doubt
that the defendant was convinced to a moral certainty that
the recipient was a minor. It's not enough for the
Commonwealth to prove that the [d]efendant merely suspected
that there was a probability that the recipient was a
minor."

We disagree.

The requested jury instruction confused the requirement

that the Commonwealth prove the elements beyond a reasonable

doubt and the meaning of a defendant's belief. A defendant need

not believe a proposition beyond a reasonable doubt to believe

it, as a reasonable doubt is not equivalent to disbelief.

Rather, the proper instruction was that the Commonwealth had to

prove beyond a reasonable doubt that the defendant believed the

recipient to be a minor.

At the charge conference with the parties, the judge

explained that he declined to give the instruction as requested

because his intended definition of reasonable doubt would be

tied to all the elements. Because the defendant objected to the

judge's ruling denying that instruction, we review for

prejudicial error. See Commonwealth v. Kelly, 470 Mass. 682,

687 (2015).
10

"A trial judge is not required to instruct the jury in the

terms requested by a defendant so long as the substance of the

requested instructions is adequately covered." Commonwealth v.

Sinai, 47 Mass. App. Ct. 544, 547 (1999). Indeed, "[j]udges

have broad discretion in framing jury instructions, including

determining the appropriate degree of elaboration."

Commonwealth v. Toolan, 490 Mass. 698, 708 (2022).

Here, the judge properly instructed the jury that they were

required to find, beyond a reasonable doubt, in addition to the

other elements, "that the defendant intentionally disseminated

the [harmful] matter to a person he knew or believed to be a

minor." He repeated this when he defined the elements.

Important to the defendant's claim, the judge also instructed

the jury that "beyond a reasonable doubt" requires the jurors

have in their "minds an abiding conviction to a moral certainty

that the charge is true," and that "[i]t is not enough for the

Commonwealth to establish a probability, even a strong

probability, that the defendant is more likely to be guilty than

not guilty." This was a correct statement of the law, and

adequately conveyed the substance of the correct portion of the

requested instruction. See Sinai, 47 Mass. App. Ct. at 547.

There was no error.

3. Lost or destroyed evidence. Finally, the defendant

claims that the judge erred in three ways, delineated below, in
11

how he addressed the Commonwealth's failure to preserve pieces

of potentially exculpatory evidence, which included the original

profile photograph used by Officer Phelan on the social media

platform account and that officer's original post to the online

group.

First, the defendant claims that the judge abused his

discretion by denying the motion to dismiss his indictments

based on the Commonwealth's failure to preserve the above-noted

pieces of evidence. We disagree.

"We will not disturb a judge's decision regarding the

proper remedy for the loss of evidence absent a clear abuse of

discretion." Commonwealth v. Meas, 467 Mass. 434, 448, cert.

denied, 574 U.S. 858 (2014), quoting Commonwealth v. Carr, 464

Mass. 855, 870 (2013). For charges to be dismissed due to the

loss or destruction of potentially exculpatory evidence, the

defendant bears an initial burden to establish a "reasonable

possibility, based on concrete evidence rather than a fertile

imagination," Commonwealth v. Neal, 392 Mass. 1, 12 (1984),

quoting State v. Michener, 25 Or. App. 523, 532 (1976), that the

evidence would have been favorable to him. See Commonwealth v.

Rios, 496 Mass. 11, 31 (2025); Commonwealth v. Olszewski, 416

Mass. 707, 714 (1993), cert. denied, 513 U.S. 835 (1994). "If

the defendant meets that initial burden, 'a balancing test is

employed to determine the appropriateness and extent of remedial
12

action.'" Commonwealth v. Moore, 480 Mass. 799, 811 (2018),

quoting Commonwealth v. Willie, 400 Mass. 427, 432 (1987),

abrogated in part on other grounds by Commonwealth v. Williams,

455 Mass. 706, 714-719 (2010). The judge 'must weigh the

culpability of the Commonwealth, the materiality of the

evidence, and the potential prejudice to the defendant.'"

Moore, supra, quoting Willie, supra.

As an initial matter, relative to the missing profile

photograph,5 as the Commonwealth notes, in fashioning a jury

instruction on the matter, the judge did not appear to have

properly analyzed the defendant's initial burden. The judge

told the parties that "the defendant has sustained [his] initial

burden, at least, of demonstrating that [the] missing

evidence . . . [is] potentially relevant here . . . ." Mere

relevance, however, differs in kind from evidence that provides

a reasonable possibility that the missing photograph would have

been favorable to the defendant. See Neal, 392 Mass. at 12.

The missing profile photograph would have been favorable to

the defense only if Phelan appeared to be older than she

appeared in the other two photographs that were before the jury.

In similar fashion, the original post to the online group would

5 Relative to Phelan's original post to the online group,
the judge stated he was "less persuaded" that it satisfied the
"standard of being potentially exculpatory."
13

have been favorable to the defendant only if it gave credence to

his argument that he and the undercover officer were simply

engaging in "role-play," or if the original post was markedly

different in tone from the officer's initial direct messages

with the defendant in which she asks the defendant his age,

where he was from, and whether he was "good" with her being

"14."

Relative to these matters, the defendant was able to use

the missing evidence to his benefit through his own testimony.

The defendant testified that he thought the person he was

communicating with was an adult posing as a child. He claimed

that she looked older in the missing profile photograph, and he

claimed that her initial post was more explicit, stating that

she would "do anything [he] want[ed]." At bottom, this did not

establish a "reasonable possibility, based on concrete evidence

rather than a fertile imagination," that the missing evidence

would have been favorable to him (citation omitted). Neal, 392

Mass. at 12.

Even if the defendant did meet his original burden, his

claim does not survive the balancing test. As to the

Commonwealth's culpability, contrary to the defendant's claim,

the judge found that the officer was not "morally culpable" for

the destruction which resulted from her lack of experience.

This was supported by the officer's testimony. Even though the
14

judge believed that she could have preserved the account without

deleting the photograph, he did not find her to be dishonorable

in purpose. In the end, this amounts to negligence, and the

defendant failed to establish bad faith. See Commonwealth v.

Heath, 89 Mass. App. Ct. 328, 337 (2016). See also Willie, 400

Mass. at 432 (Commonwealth not required "to prove good faith or

earnest efforts to preserve the evidence").

The remaining components of the balancing test, materiality

and potential prejudice, do not redound to the defendant's

benefit. While the missing items could have been material to

whether the defendant believed Phelan was actually an adult, the

defendant capitalized on the absence of evidence to further his

theory that he knew he was communicating with an adult. See

Commonwealth v. Kee, 449 Mass. 550, 555-557 (2007) (no prejudice

where defendant used unpreserved evidence to aid defense). In

the end, the denial of the motion to dismiss was not an abuse of

discretion, nor was the denial of the motion without an

evidentiary hearing.6

Second, the defendant claims that the judge abused his

discretion by permitting Phelan to testify regarding the

original message that she posted to the online social media

6 The defendant has failed to cite to relevant legal
authority for his argument that the judge ought to have
conducted an evidentiary hearing on this issue.
15

group. For the first time on appeal,7 the defendant claims this

violated the best evidence rule which mandates reversal of his

convictions. We disagree.

"The best evidence rule provides that, where the contents

of a document are to be proved, the party must either produce

the original or show a sufficient excuse for its nonproduction."

Commonwealth v. Ocasio, 434 Mass. 1, 6 (2001). See Mass. G.

Evid. § 1002 (2026). A sufficient excuse for nonproduction may

arise when evidence is "lost or destroyed, and not by the

proponent acting in bad faith" (citation omitted). Commonwealth

v. Connolly, 91 Mass. App. Ct. 580, 585 (2017).

The defendant claims that Phelan's practice of introducing

herself as a fourteen year old went to the heart of the issue

the jury had to decide, i.e., whether the defendant believed she

was a minor. Even assuming the Commonwealth used the testimony

to prove the content of the posting, and the rule therefore

applied, the exception may be applied for nonproduction because

the original post was lost or destroyed, and that destruction

7 At trial, the defendant objected to Phelan's testimony
because he did not have copies of the social media post. He did
not claim her testimony violated the best evidence rule. The
Commonwealth argues that the claim is not preserved and may be
reviewed only to determine if a substantial risk of a
miscarriage of justice was created. In his reply brief, the
defendant does not argue to the contrary.
16

was not done in bad faith. See Connolly, 91 Mass. App. Ct. at

585.

The defendant correctly maintains that for the exception to

apply, the judge must have made findings that the original

posting once existed, its loss or destruction was not due to the

"serious fault" of the Commonwealth, and that a reasonable

search had been made for the post. See Ocasio, 434 Mass. at 6-

7, quoting Fauci v. Mulready, 337 Mass. 532, 540 (1958). While

the judge did not expressly make these findings, the lack of an

objection and a request for such findings is undoubtedly the

reason why. In any event, the one-time existence of the posting

was never in dispute, nor that it no longer existed because it

had been deleted. The judge did find that the officer had not

acted in bad faith and stated that he did not find her to be

"morally culpable." In fact, when the judge denied the

defendant's objection to Phelan's testimony about what she

wrote, the judge told the defendant, "Well, I've ruled that I'm

not going to dismiss the indictment based upon that." In this

light, the judge did not abuse his discretion by admitting the

officer's testimony as a substitute for the original posting.8

Relying on Commonwealth v. Salyer, 84 Mass. App. Ct. 346,
8

356 n.10 (2013), the defendant claims that oral testimony is not
permitted to prove the contents of a document. While this is
true in general applications of the rule, we noted in Salyer
that "none of the exceptions that permit the use of secondary
evidence was applicable." Id. In other words, Salyer did not
17

Even if the judge "made a clear error of judgment in

weighing the factors relevant to the decision such that the

decision falls outside the range of reasonable alternatives"

(quotation and citation omitted), L.L. v. Commonwealth, 470

Mass. 169, 185 n.27 (2014), the defendant has failed to

establish that the testimony created a substantial risk of a

miscarriage of justice. In addition to the strength of the

Commonwealth's case, we keep in mind that the best evidence rule

is "a doctrine of evidentiary preference 'principally aimed, not

at securing a writing at all hazards and in every instance, but

at securing the best obtainable evidence of its contents'"

(emphasis omitted). Ocasio, 434 Mass. at 6, quoting 2

McCormick, Evidence § 237 (5th ed. 1999). In the posture of

preference over prohibition, we also return to the effect of the

testimony, and, as stated above, how the defendant used it in

involve lost or destroyed evidence. Moreover, there is no
blanket prohibition on utilizing oral testimony as secondary
evidence. See Commonwealth v. Brea, 488 Mass. 150, 159 n.12
(2021) (permitting testimony as secondary evidence of content of
record); O'Connor v. Boston Retirement Bd., 304 Mass. 471, 472-
473 (1939) (retiree's written change of beneficiary form and
acknowledgement that could not be located by board "properly
shown by oral evidence"); Grover v. Smead, 295 Mass. 11, 13
(1936) (car owner's oral testimony regarding contents of
original certificate of registration that had been lost or
destroyed was properly admitted). See also 20 W.G. Young, J.R.
Pollets & C. Poreda, Evidence § 1008.1 (2d ed. 1998)
("Massachusetts does not recognize 'degrees of secondary
evidence . . .'").
18

his defense, including his testimony that he thought he was

communicating with an adult posing as a child.

Third, the defendant claims the judge abused his discretion

in his jury instruction regarding lost or destroyed evidence

because the instruction mentioned only the profile photograph

and not Phelan's introductory text messages.9 We disagree.

The judge explained that the instruction referenced only

the photograph, and not the text messages, because he was not

convinced of the potential exculpatory nature of the messages.

In contrast to the profile photograph, the text messages did not

relate to the harmful materials, and were merely preliminary

conversations that did not go "directly to the issue of how

someone goes about determining whether they're dealing with a

minor." Furthermore, the judge noted that defense did not argue

entrapment, which he thought might have made the text messages

exculpatory. On the other hand, he stated that the profile

photograph went directly to the issue of the defendant's belief

regarding "Crayon Mia's" age.

Given the judge's determination that the introductory text

messages did not possess a potential exculpatory value and his

9 The judge instructed as follows: "Lost or Destroyed
Exculpatory Evidence. You have heard that the initial [social
media platform] profile photo[graph] utilized by Officer Phelan
for the profile at issue in this case was not preserved by her.
You may but are not required to infer that if this evidence had
been preserved, it would have been favorable to the defendant."
19

finding that the defendant, "as a practical matter," was able to

testify as to his recollections of what the messages stated as

part of his defense, the judge concluded that he would leave it

to the jury to decide what to credit. On this record, in

fashioning the instruction, we cannot conclude that the judge

"made a clear error of judgment in weighing the factors relevant

to the decision such that the decision falls outside the range

of reasonable alternatives" (quotation and citation omitted).

L.L., 470 Mass. at 185 n.27.

Judgments affirmed.