United States v. Cabrera

Decision Date08 September 2021
Docket NumberNo. 19-3363-cr,August Term 2020,19-3363-cr
Citation13 F.4th 140
Parties UNITED STATES of America, Appellee, v. John E. CABRERA, Defendant-Appellant.
CourtU.S. Court of Appeals — Second Circuit

DANIEL HABIB, Federal Defenders of New York, New York, NY, for Defendant-Appellant John Cabrera.

DANIELLE R. SASSOON, Assistant United States Attorney (Dominic Gentile, Rebekah Donaleski, Thomas McKay, Assistant United States Attorneys, on the brief), United States Attorney's Office for the Southern District of New York, New York, NY, for Appellee.

Before: JACOBS, LYNCH, SULLIVAN, Circuit Judges.

JUDGE SULLIVAN dissents in the Court's opinion, and files a dissenting opinion.

Dennis Jacobs, Circuit Judge:

John Cabrera engaged in four drug transactions with his barber, who was a government informant. Cabrera's sole defense was entrapment, which (as the district court acknowledged) was a close call as to the element of inducement. He appeals chiefly on the grounds that: the charge misstated his burden by requiring the defendant to establish that the government initiated the crime; and that testimony from a special agent, who opined that Cabrera was an experienced drug dealer, was inadmissible as lay opinion under Federal Rule of Evidence 701.

Cabrera and his barber gave opposite accounts of who first proposed partnering in the drug trade. It was therefore crucial that the charge accurately state Cabrera's burden: the slight burden of adducing "some credible" evidence that the government initiated the crime. The charge overstated that burden, effectively requiring that the jury weigh the evidence and definitively accept Cabrera's account as a precondition to considering predisposition.

Compounding the prejudice to Cabrera's defense, the special agent's testimony that Cabrera was an "experienced" drug dealer was inadmissible as lay opinion. And it undercut Cabrera's account of how the transactions with his barber originated, as well as his lack of predisposition to deal.

We vacate Cabrera's conviction and remand for a new trial.

I

Cabrera is a legal permanent resident who came to New York from the Dominican Republic in 2013, when he was 20. After arriving, Cabrera held several minimum-wage jobs before becoming a carpenter. Around 2014, he met a barber and fellow Dominican immigrant named Marcos. Cabrera's apartment was located near the barbershop where Marcos worked, and Cabrera began visiting him weekly for a shave and haircut.

Marcos had immigrated to the United States in 1992 when he was 17; but in 2001 he was deported after serving a sentence on a drug conviction. He reentered illegally that same year. In 2016 Marcos became a paid informant for the Drug Enforcement Administration ("DEA"). He received cash payments and deportation deferrals renewed annually so long as he remained an informant. (Put another way, Marcos was compensated and deferred so long as he was useful, that is, so long as he had people on whom he could inform.)

Over a two month period in late 2017, Cabrera and Marcos partnered to sell drugs. Cabrera delivered pills containing fentanyl, and Marcos, under the DEA's direction, paid Cabrera and pretended to resell the pills to customers in North Carolina. There were five transactions. On September 7, Cabrera gave Marcos a small free sample. Six days later, Cabrera sold Marcos 200 pills for $3,000; a week later, 198 pills for $3,000; and another six days later, 397 pills for $3,000 up front and $3,000 in two days. Following a month-long gap, they met again on October 27 to exchange 1,000 pills for $15,000, and agents arrested Cabrera; he had 1,100 pills on him.

The government charged Cabrera in a four-count indictment. Counts I and II were for distributing and possessing with intent to distribute fentanyl on September 13 and 21 in violation of 21 U.S.C. §§ 812, and 841(a)(1) and (b)(1)(C). Counts III and IV were for distributing and possessing with intent to distribute 40 grams or more of fentanyl on September 27 and October 27 in violation of 21 U.S.C. §§ 812, and 841(a)(1) and (b)(1)(B). At trial, Cabrera and Marcos gave sharply divergent testimony about how their partnership began.

Cabrera--conceding he sold the pills to Marcos--claimed he was entrapped. He testified as follows. Marcos asked him several times during barbershop visits to supply drugs; Cabrera refused, telling Marcos he already made sufficient money as a carpenter. But Marcos renewed his invitation approximately five or six times until, in early 2017, Cabrera relented, having become desperate after losing his job, girlfriend, and apartment--and confiding his problems to Marcos. Cabrera began searching for a supplier; after six months, he found one at a nightclub, and told Marcos that he was ready: Cabrera would serve as the middleman, earning $2 from the supplier for each pill that he sold to Marcos, who would then resell to (fictitious) customers in North Carolina.

Marcos's version of events, as follows, was different in every material respect. Marcos first learned in 2016 that Cabrera dealt drugs when Cabrera told him that his supplier had unfortunately been arrested. At that point, Cabrera and Marcos had known each other for eight months. Cabrera then disappeared for a year, during which time Marcos became an informant. When Cabrera returned to the barbershop in September 2017, he told Marcos that he was back in business. Cabrera was looking to sell oxycodone pills and asked Marcos if he knew any buyers. When Marcos said that he knew some in North Carolina, Cabrera proposed that the two do business together. Marcos promptly contacted his handlers at the DEA.

Trial evidence included government recordings of meetings and phone calls between Cabrera and Marcos, all of which post-date the agreement to partner. Cabrera boasted of his experience selling drugs, telling Marcos, for example, that "with me there will always be many good things," and "I'm only 24 ... but I'm not new at this." App'x 80–81. Cabrera and Marcos occasionally pushed each other to do bigger deals. At their second meeting (their first sale), Marcos voiced frustration at being unable to buy pills in greater bulk; and soon after, over the phone, Cabrera expressed disappointment about how long it was taking to plan their next deal. On a call following their third meeting, Cabrera urged Marcos to visit North Carolina more frequently; when Marcos demurred, Cabrera offered to give him more pills on credit. Later, Marcos asked Cabrera to locate a pure form of heroine called China White, but this time it was Cabrera who declined.

Cabrera went silent after their September 29 meeting. He testified that he wanted to cut ties with Marcos because he regretted breaking the law and feared he was under DEA surveillance. Marcos left multiple voicemails throughout October, pushing Cabrera to resume deals. At the DEA's direction, Marcos showed up at Cabrera's workplace to ask where he had been (Marcos does not recall being wired on that occasion). On October 25 at the barbershop, they planned the fifth deal in an unrecorded meeting; according to Marcos, Cabrera was scared he had been followed and insisted on increasing the deal to 1,000 pills.

Special Agent Daniel Son, who had surveilled Cabrera at the September 21 and 27 deals, also testified. Over Cabrera's objection, Agent Son opined on rebuttal that Cabrera, unlike the "average drug dealer," appeared to be "experienced" because he had employed countersurveillance driving techniques (which consisted of really bad driving). App'x 649. For support, Agent Son cited his experience conducting narcotics investigations.

After a six-day trial, the jury convicted Cabrera on all counts. Cabrera was sentenced to concurrent terms of 48 months’ imprisonment on each count.

II

The first issue is whether the jury instruction on Cabrera's entrapment defense contained error, specifically as to the element of inducement. "We review a jury instruction challenge de novo ." United States v. Coppola, 671 F.3d 220, 247 (2d Cir. 2012) (citation omitted). "Instructions are erroneous if they mislead the jury as to the correct legal standard or do not adequately inform the jury of the law." Hudson v. New York City, 271 F.3d 62, 67 (2d Cir. 2001) (quotation omitted).

A

The affirmative defense of entrapment consists of "two related elements: government inducement of the crime, and a lack of predisposition on the part of the defendant to engage in the criminal conduct." Mathews v. United States, 485 U.S. 58, 63, 108 S.Ct. 883, 99 L.Ed.2d 54 (1988) (citations omitted). "[W]hen a defendant has presented credible evidence of inducement by a government agent, the government has the burden of proving beyond a reasonable doubt that the defendant was predisposed to commit the crime." United States v. Flores, 945 F.3d 687, 717 (2d Cir. 2019) (citing Jacobson v. United States, 503 U.S. 540, 548–49, 112 S.Ct. 1535, 118 L.Ed.2d 174 (1992) ).

That approach balances two considerations. The government may not manufacture crime where there would be none by "implant[ing] in the mind of an innocent person the disposition to commit the alleged offense and induc[ing] its commission ...." Jacobson, 503 U.S. at 553, 112 S.Ct. 1535 (quoting Sorrells v. United States, 287 U.S. 435, 442, 53 S.Ct. 210, 77 L.Ed. 413 (1932) ). At the same time, "stealth and strategy are necessary weapons in the arsenal of the police officer." Sherman v. United States, 356 U.S. 369, 372, 78 S.Ct. 819, 2 L.Ed.2d 848 (1958). The entrapment defense thus seeks to protect the "unwary innocent" while leaving room for investigative techniques that catch the "unwary criminal who readily availed himself of the opportunity to perpetrate the crime." Mathews, 485 U.S. at 63, 108 S.Ct. 883 (quotation omitted).

The first element--inducement--is relatively straightforward. It happens when the government has "initiated the crime." United States v. Brand, 467 F.3d 179, 190 (2d Cir. 2006) (quoting United States v. Mayo...

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