Ediscovery ALERT | Nixon Peabody LLP
October 3, 2014
Instant messages as evidence: questions of
authenticity and admissibility addressed in
Massachusetts Appeals Court ruling
By Jonathan Sablone and Steven M. Richard
Courts are confronting novel and at times vexing evidentiary questions in their review of electronic
communications, such as text or instant messages. In both civil and criminal cases, electronic
dialogue can offer captivating and compelling evidence, particularly because the informality and
fast pace of the media often elicit unguarded and unfiltered statements by its users. Litigants are
contesting and courts must adjudicate the necessary foundational requirements to authenticate
whether a string of electronic communications is complete, whether there has been any alteration
of the contents and who actually wrote the communications. Even after these authenticity
thresholds have been cleared, evidentiary issues still remain whether the communications should
be admitted in whole or in part and, if admitted, whether a trial judge should give any limiting or
specialized instructions to guide the jury’s review. In Commonwealth v. Oppenheim,1 the
Massachusetts Appeals Court addressed such evidentiary concerns in upholding a criminal
conviction in which an incriminating instant message (IM) confession was shown by credible
evidence to have been authored by the defendant.2
Background
The defendant, David Oppenheim, and his wife founded and operated a community theater center,
where he directed musical theater and taught acting classes. The Commonwealth of Massachusetts
brought rape charges against Oppenheim arising from his inappropriate sexual conduct toward a
minor that he privately mentored at the center. The Commonwealth’s main witness, Ann Ross (a
pseudonym), testified that she began attending the center in 2004 at age thirteen and that
Oppenheim encouraged her to take private acting lessons in 2005. Over the next two years during
1
Slip Opinion, No. 12-P-1673 (Mass. App. Ct. Sept. 24, 2014).
2
“Instant messaging is ‘a form of computer communication in which individuals hold an online conversation via
the [I]nternet . . . . [The] message is transmitted instantaneously . . . allow[ing] both parties . . . to respond
immediately.” Slip op. at 2 n.2 (quoting Commonwealth v. Disler, 451 Mass. 216, 218 n. 3 (2008), internal quotation
from State v. Lott, 152 N.H. 436, 437 (2005))
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their private sessions, Oppenheim sexually assaulted Ross on multiple occasions at the center and
his residence.
The Commonwealth’s second principal witness, Ryan DiMartino, joined the center at age thirteen
in 2005 and participated in its programs for several years.3 Beginning in October 2007, Oppenheim
and DiMartino engaged in online chats, which involved discussions of personal matters and
intensified to flirtatious and sexual content. Beginning in February 2008, Oppenheim made physical
advances toward DiMartino when they interacted at the center.
On February 13, 2008, Oppenheim warned DiMartino that he needed to avoid any suspicion by
DiMartino’s parents or others about their instant message traffic. Oppenheim suggested that he
open a new online account with a new online name, changing his IM identity to “Allie.” On March
9, 2008, DiMartino and Oppenheim were together at the center and discussed Ross, to whom
DiMartino had an undisclosed physical attraction. When Oppenheim encouraged DiMartino to
pursue a relationship with Ross, DiMartino asked Oppenheim if he was involved sexually with
Ross. Oppenheim responded that they could “talk about it another time.” The next day, on March
10, 2008, Oppenheim engaged in an IM conversation with DiMartino in which Oppenheim
described in detail his first seduction of Ross when she was fourteen. Oppenheim also related that
he had maintained a pattern of sexual intercourse with Ross during their private meetings.
The Commonwealth also presented testimony from a former student who recounted that
Oppenheim told her of his sexual relationship with Ross and by two other former students who
described Oppenheim’s inappropriate sexual advances toward them. A jury convicted Oppenheim
of five counts of rape of a child, and he appealed his conviction to the Massachusetts Appeals
Court.
Authenticating and admitting the IM evidence
At both the trial and appellate levels, Oppenheim contested vigorously the introduction of the
instant messages. Before the trial court, the Commonwealth relied upon DiMartino’s testimony to
authenticate the messages and provide the foundational support for their admission into evidence.
DiMartino testified regarding the history of the online communications with Oppenheim,
Oppenheim’s changing of his online name to shield his identity and their in-person discussion
about Ross on March 9, 2008, just one day before the incriminating March 10 instant messages.
DiMartino was convinced that Oppenheim authored the March 10 messages based on their tone
and language and their references to personal matters that the two of them previously shared with
one another.
Oppenheim raised several objections to the admission of the electronic communications, especially
because the Commonwealth did not conduct a forensic examination of DiMartino’s computer. On
cross-examination, DiMartino conceded that it is conceivable that someone can hack into an
instant messenger account and that it is very easy to download an IM communication and alter it.
DiMartino also acknowledged that he did not produce all of the IM communications when he first
spoke to the police.
3
DiMartino was born and raised as a female and later transitioned to a male after the events at issue in the criminal
case.
In admitting the evidence over Oppenheim’s objection, the trial judge relied upon the
Massachusetts Supreme Judicial Court’s holding in Commonwealth v. Purdy, 459 Mass. 442 (2011),
which upheld the admission of e-mails upon proof of “confirming circumstances” sufficient for a
reasonable jury to find by a preponderance of the evidence that the defendant authored the
electronic communications. The trial judge also applied Massachusetts Rule of Evidence
§ 901(b)(11)(applicable to “Electronic or Digital Communications”), which codifies the
“confirming circumstances” standard and does not require expert testimony or exclusive access to
authenticate the source. The trial judge determined that DiMartino’s testimony about her in-person
and electronic interactions with Oppenheim sufficiently corroborated that the messages were a
conversation between DiMartino and the defendant to support their admissibility into evidence.
The trial judge ruled that any issues about whether someone else could have typed the conversation
went to the weight of the evidence for the jury’s consideration. The trial judge carefully instructed
the jury that it must find, by a preponderance of the evidence, Oppenheim to be the author of the
IM confession before considering its contents.
On appeal, Oppenheim argued that the trial judge should have instructed the jury that, before it
could consider a confession in an IM conversation, the Commonwealth must prove beyond a
reasonable doubt (not a preponderance of the evidence) that the defendant authored the
confession. Oppenheim contended that the reasonable doubt standard should apply to the
admissibility of online admissions and the jury’s acceptance of them because (1) confessions carry
probative force and (2) online communications are susceptible to impersonation or fabrication,
especially in the absence of forensic computer confirmation. The Massachusetts Appeals Court
rejected Oppenheim’s arguments on three grounds.
First, the appellate court found no error with the standard of proof applied by the trial judge in
reviewing and admitting the evidence for the jury’s consideration. While it “is axiomatic” that the
prosecution must establish each element of a crime by proof beyond a reasonable doubt, the
“prevailing rule” in the Commonwealth is that the preponderance of the evidence standard applies
to resolve “preliminary facts” (such as the authenticity and admissibility of the instant messages).
The appellate court ruled that the trial judge properly relied upon and applied Commonwealth v.
Purdy, in concluding that a reasonable jury could find by a preponderance of the evidence that
Oppenheim authored the IM confession. Citing to United States Supreme Court precedent, the
appellate court held that the preponderance of evidence standard, not the higher beyond a
reasonable doubt standard, applies to admissibility questions and the jury’s consideration of facts,
even when such facts like the instant messages in this case are highly probative of guilt.
Second, the appellate court concluded that the trial record sufficiently showed “confirming
circumstances” corroborating the authenticity of the IM and Oppenheimer as author of the
incriminating statements. DiMartino’s testimony provided the necessary “confirming
circumstances,” describing the IM sender’s references to intimate and personal details that
DiMartino and Oppenheim previously shared. Acknowledging the defendant’s argument that
DiMartino knew of these details and could have manufactured their appearance in the IM, the
appellate court concluded that such an “effort would have been elaborate and generally
inexplicable.” Like the trial court, the appellate court concluded that any challenges to what the
messages purported to be were more appropriately directed to their weight, not their admissibility.
Third, the appellate court rejected Oppenheim’s invocation of the “humane practice rule,” which
compels the disregarding of an incriminating confession attributed to the defendant unless the
prosecution proves beyond a reasonable doubt that the statements were made voluntarily. The
appellate court found this rule to be inapplicable to the electronic confession presented in this case.
The rule is designed to preclude coerced confessions, which was not the situation with the instant
messages passed between two private individuals engaged in a voluntary electronic communication.
In upholding the trial court’s evidentiary rulings admitting the instant messages, the
Massachusetts Appeals Court provided the following summation:
[I]n response to an objection to the authenticity or authorship of a self-inculpatory
electronic message, the judge will determine its admissibility and the jury its
credibility by a reasonable preponderance of the evidence. Counsel will be able to
contest both issues by argument regarding the presence or absence of confirming
circumstances.
Takeaways from the case
Although Oppenheim was a criminal matter and raised issues particular to such proceedings (e.g.,
the extent to which a “reasonable doubt” standard applies), it offers important lessons for all cases
as litigants must address the impact of electronic communications and the scope to which such
evidence will be admitted. Like all forms of evidence, electronic communications—such as IM or
text messages—must be properly authenticated in order to be admitted. Where electronic
communications may identify a sender by a pseudonym or may be suspect to manipulation,
evidence of distinctive characteristics or “confirming circumstances” will be vital to show that the
electronic communication is what it is claimed to be. If a forensic examination has not been
undertaken or supportive expert testimony has not been obtained, litigants must often depend on
the credibility of factual witness and the persuasiveness of the circumstantial evidence, which can
be minimized or negated through cross-examination if not properly vetted and substantiated before
their presentation at trial.
Counsel and parties should review whether a jurisdiction has specifically adopted rules of evidence
applicable to electronic communications, such as Massachusetts Rule of Evidence § 901(b)(11),
which was applied in Oppenheim. All evidentiary considerations applicable to electronic
communications, such as instant or text messages, must be carefully analyzed and understood
because of their potentially dispositive impact upon the questions of liability and damages in civil
cases and guilt or innocence in criminal cases.
For more information on the content of this alert, please contact your Nixon Peabody attorney or:
— Jonathan Sablone at jsablone@nixonpeabody.com or (617) 345-1342
— Steven M. Richard at srichard@nixonpeabody.com or (401) 454-1020