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SJC-12272

                  COMMONWEALTH   vs.   SCYPIO DENTON.



              Essex.     March 9, 2017. - June 1, 2017.

 Present:    Gants, C.J., Lenk, Hines, Gaziano, Lowy, & Budd, JJ.


Controlled Substances.      Entrapment.   Evidence, Prior conviction.



     Indictment found and returned in the Superior Court
Department on February 6, 2014.

     The case was tried before James F. Lang, J.

     The Supreme Judicial Court on its own initiative
transferred the case from the Appeals Court.


     James E. Methe for the defendant.
     Quentin R. Weld, Assistant District Attorney (Elin H.
Graydon, Assistant District Attorney, also present) for the
Commonwealth.


     BUDD, J.    Following a jury trial, the defendant, Scypio

Denton, was convicted of distribution of heroin, in violation of

G. L. c. 94C, § 32 (b). 1    At trial, the defendant raised the


     1
         Following his conviction on the substantive crime, the
                                                                        2


affirmative defense of entrapment.      The judge permitted the

Commonwealth to respond by introducing evidence of three prior

convictions, despite the defendant's objection that they were

too stale to be probative of his predisposition to commit the

crime.      The defendant's principal argument on appeal concerns

the decision to admit this evidence. 2     We reverse on that ground.

     Background.      We recite the facts the jury could have found.

     1.      2013 distribution.   On December 17, 2013, the defendant

was approached by an undercover police officer posing as a drug

addict. 3    The officer told the defendant he "was dope sick and

. . . looking to get hooked up . . . because [he] wasn't feeling

well."      He asked the defendant for "a forty" of "brown" 4 and

explained that his dealer was not answering his telephone calls

because he owed the dealer money.      At the time of the undercover

operation, there was an unwritten rule among drug users that if


defendant pleaded guilty to being a subsequent offender. The
judge sentenced the defendant to from three and one-half years
to three and one-half years and one day in State prison, the
mandatory minimum sentence for subsequent drug offenders.
     2
       We transferred the case from the Appeals Court to this
court on our own motion.
     3
       During his sixteen years working undercover, the police
officer had made approximately 850 undercover purchases. On the
day that the officer approached the defendant, the officer and
his colleagues were not focused on any one individual, but
rather on reducing open-air drug sales in the area.
     4
       The officer explained that this was a reference to an
amount of heroin worth forty dollars.
                                                                    3


somebody was "dope sick" from heroin withdrawal, another user

would help them to find more heroin, as he or she could

sympathize with the feeling. 5   The officer believed that this

approach for targeting heroin distribution was successful

approximately twenty to thirty per cent of the time.

     The defendant agreed to help, and they got into an unmarked

motor vehicle driven by another undercover officer.    While they

were in the vehicle, the defendant used an officer's cellular

telephone to tell someone that "he wanted to come by and grab a

bag."    They then proceeded to a destination the defendant gave

them.    When they arrived, an officer gave the defendant forty

dollars and took the defendant's cellular telephone as

collateral.    The defendant entered a building and returned with

a bag of a tan powdered substance, which he gave to the officer

who claimed to be "dope sick."    One of the officers gave the

defendant five dollars in exchange for obtaining the drugs.



     5
       At trial, the officer explained why other users would help
when someone claimed to be "dope sick":

          "[W]hen a user cannot obtain heroin to use, they
     face . . . withdrawals, ranging from sweats, to the
     chills, severe aching in the muscles and joints,
     nausea. . . . [I]t's . . . quite a bad scene . . . .
     [Drug users] understand . . . the pain and what
     they're suffering through. And they are going to do
     pretty much anything they can to help you, because at
     some point they may be in that position themselves,
     and they're going to want someone to help them out."
                                                                      4


     The tan powdered substance was later tested and found to be

a mixture of heroin and caffeine.   A warrant issued for the

defendant's arrest, which was carried out at a later date to

protect the identity of the undercover officers.

     2.   Prior convictions introduced at trial.    After the judge

determined that the defendant had raised the issue of

entrapment, the prosecutor was allowed to present the following

evidence of three former convictions to show the defendant's

predisposition to commit the crime.

     In 1993, a police officer saw the defendant place a pipe on

the floor and a bag of marijuana under a door.     The defendant

stated that he was buying drugs for two other men.     Based on the

substance found in two other bags that were found on or near the

defendant, he was ultimately convicted of possession with intent

to distribute cocaine.

     In 1994, an undercover police officer asked the defendant

to get him twenty dollars' worth of "crack" cocaine.     The

defendant agreed to help him.   The defendant went to a nearby

apartment on the officer's behalf to obtain the cocaine.       When

the defendant returned with a bag containing a substance that

looked like crack cocaine, he asked for some money for his role

in the deal.   He was again convicted of possession with intent

to distribute cocaine.
                                                                       5


     In 1991, the defendant was convicted of possession of a

class A substance with intent to distribute. 6

     Discussion.     We review evidentiary rulings for abuse of

discretion.    Commonwealth v. Dargon, 457 Mass. 387, 400 (2010).

Although admissible to show motive and modus operandi, and for

other purposes, evidence of a defendant's prior bad acts,

including evidence of past crimes, is generally inadmissible to

show a defendant's propensity to commit the crime with which he

or she is charged.    See Mass. G. Evid. § 404(b) (2017).

Cf. Alegata v. Commonwealth, 353 Mass. 287, 300 (1967) ("The

concept of 'once a criminal always a criminal' is abhorrent to

our law").    However, when a defendant raises the defense of

entrapment, the Commonwealth may respond with propensity

evidence.    See Commonwealth v. Buswell, 468 Mass. 92, 106

(2014); Mass. G. Evid. § 405(b).

     An entrapment defense is, at bottom, a claim by the

defendant that he or she ordinarily would not have committed the

charged crime had officers not enticed him or her to do so.       In

response, the Commonwealth is entitled to refute that claim by

introducing evidence to show that the defendant was predisposed

to commit the charged crime because he or she had committed

similar bad acts in the past; i.e., that police officers did not

     6
       For this crime, the prosecutor did not present the
underlying facts.
                                                                      6


entice an otherwise innocent person to commit a criminal act.

See Buswell, supra; Mass. G. Evid. § 405(b).     The bad acts must

be "sufficiently similar to the crime charged to ensure that

their probative value outweighs the strong likelihood of

prejudice." 7    Buswell, supra, citing Commonwealth v. Vargas, 417

Mass. 792, 795 (1994).

     In evaluating the admissibility of prior bad act evidence

in an entrapment case, a judge must also consider whether

sufficiently similar prior bad acts are recent enough that they

remain probative of the defendant's predisposition to commit the

charged crime.     Recent bad acts tend to show that a defendant

was predisposed to commit a similar crime, so they have strong

probative value that will likely outweigh the prejudice to the

defendant.      See Buswell, 468 Mass. at 106-107, citing Vargas,

417 Mass. at 795.     However, over time, as the defendant has had

the opportunity to reform himself or herself, the balance

between probative value and unfair prejudice shifts

incrementally toward the latter.     See Commonwealth v. Dingle, 73

     7
       This is similar to the exacting standard we employ for the
admission of prior bad act evidence by the prosecution where
there is no defense of entrapment. See Commonwealth v. Crayton,
470 Mass. 228, 249 & n.27 (2014) (prior bad act evidence is
inadmissible "if its probative value is outweighed by the risk
of unfair prejudice to the defendant"); Mass. G. Evid.
§ 404(b)(2). Contrast Mass. G. Evid. § 403 (relevant evidence
that does not concern prior bad acts is admissible unless "its
probative value is substantially outweighed by a danger of . . .
unfair prejudice" [emphasis added]).
                                                                   7


Mass. App. Ct. 274, 284 (2008) (probative value of

predisposition evidence was outweighed by its prejudice where

prior bad acts were "old, the most recent dating back more than

thirteen years"); Commonwealth v. Childs, 23 Mass. App. Ct. 33,

37-38 (1986), S.C., 400 Mass. 1006 (1987) (when introduced at

trial in 1984, prejudicial effect of prior convictions from

1950s and 1960s was more pronounced).   Thus, prior convictions

must "not be too remote in time" or they lose their probative

value as to whether the defendant was predisposed to commit this

most recent crime.   Cf. Commonwealth v. Butler, 445 Mass. 568,

574 (2005), quoting Commonwealth v. Barrett, 418 Mass. 788, 794

(1994) (probative value of prior bad acts decreases over time);

G. L. c. 233, § 21 (imposing time limits on admission of prior

convictions to impeach witness credibility).

     Here, the parties and the judge discussed at length what

evidence the prosecutor could introduce to rebut the defendant's

entrapment defense by showing that he was predisposed to commit

the crime.   The prosecutor stated her intention to elicit

testimony that would show the facts and certified convictions of

two prior cases, as well as a certified conviction from a third

case, all of which ultimately were introduced at trial.     The

defendant moved to exclude the proffered evidence of these

convictions, arguing that their age made them more prejudicial

than probative.   The judge denied the motion to exclude,
                                                                        8


concluding that the possible prejudicial impact of the evidence

did not outweigh their probative value.

     The judge appeared to have given the age of the convictions

careful consideration.   However, in the circumstances of this

case it was error to admit the prior bad acts.   Although the

facts in at least two of the defendant's prior cases bore a

remarkable similarity to those in this case (i.e., acting as a

"middleman" in a drug transaction), the initially high probative

value of the convictions dropped sharply over time.    The acts

underlying the convictions all took place in or before

1994, nineteen years before the crime charged in this case.       The

Commonwealth was unable to identify any case where past crimes

this old were used as propensity evidence to rebut an entrapment

defense; nor have we found any.   See Dingle, 73 Mass. App. Ct.

at 284 (evidence of bad acts from thirteen or more years earlier

was erroneously admitted).   Here, where the most recent act was

at least nineteen years old, the probative value regarding

predisposition no longer outweighed the potential prejudice to

the defendant.   In addition, the limiting instruction 8 to the

jury was insufficient to mitigate the error given the inherent


     8
       The judge instructed: "You may consider this evidence
solely for whatever light it sheds on the issue of whether the
[d]efendant was predisposed and ready to commit the offense with
which he is charged. You are not to consider it for any other
purpose."
                                                                 9


dangers in admitting evidence of predisposition.    See,

e.g., Whiting v. United States, 296 F.2d 512, 516 (1st Cir.

1961) (cautioning that admission of prior convictions "is

subject to the defects inherent in any retrospective appraisal

of past conduct").

     Conclusion.     Because the introduction of the prior

convictions was not harmless error, a new trial is required. 9

                                      Judgment reversed.

                                      Verdict set aside.




     9
       The defendant further attributes error to the introduction
of a statement by a retired police officer who testified
regarding a prior conviction and to the imposition of a
mandatory minimum sentence. He also argues that the prosecutor
erred in remarking that jurors are average people who would not
know vernacular drug terms, referring to undercover police
operations in other types of criminal cases, and stating that
the Commonwealth did not have sufficient evidence to charge the
dealer. Because we conclude that evidence of the defendant's
prior convictions warrants a new trial, we need not address
these arguments.
