── Commonwealth v. Milan ──
Court: Massachusetts Appeals Court
Date: May 14, 2026
Category: General
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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
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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
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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 provid