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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.