United States v. Serrano-Delgado

• Decision Date: 22 March 2022
• Docket Number: No. 19-1652,19-1652
• Citation: 29 F.4th 16
• Parties: UNITED STATES of America, Appellee, v. Cristian SERRANO-DELGADO, Defendant, Appellant.
• Court: U.S. Court of Appeals — First Circuit

29 F.4th 16

UNITED STATES of America, Appellee,

v.Cristian SERRANO-DELGADO, Defendant, Appellant.

No. 19-1652

United States Court of Appeals, First Circuit.

March 22, 2022

Victor Gonzalez-Bothwell, Assistant Federal Public Defender, with Eric Alexander Vos, Federal Public Defender, Franco L. Pérez-Redondo, Assistant Federal Public Defender, and Liza L. Rosado-Rodríguez, Research and Writing Specialist, on brief, for appellant.

David C. Bornstein, Assistant United States Attorney, with whom W. Stephen Muldrow, United States Attorney, and Mariana E. Bauzá-Almonte, Chief, Appellate Division, were on brief, for appellee.

Before Howard, Chief Judge, Thompson and Kayatta, Circuit Judges.

KAYATTA, Circuit Judge.

Cristian Serrano-Delgado drove a car that transported two passengers to and from a robbery of a bar, during which one of his passengers killed an off-duty police officer. The government charged all three men with conspiracy to commit a robbery, committing the robbery, and discharging a firearm in relation to a crime of violence resulting in death. The two men who held up the bar negotiated guilty pleas, but Serrano opted to go to trial. After a jury found him guilty on all counts, the district court sentenced him to thirty years in prison. Serrano now challenges several aspects of his trial and sentence. Finding none of his challenges availing, we affirm.

I.

A.

The events of this case occurred on a single night in 2017, during which Herol Café -- a bar and restaurant in Ponce, Puerto Rico -- was robbed and a patron was killed. Before the robbery, Serrano had been driving two other men (Jonathan Valentín-Santiago and Rubén Miró-Cruz) through the streets of Ponce. Security cameras recorded his car as he drove past Herol Café three times in five minutes. After the third pass-by, Serrano parked the car up the block and pointing away from the bar, even though there was plenty of parking much closer to the bar on both sides of the street.

Valentín and Miró got out of the car and headed toward Herol Café. Serrano waited near the trunk of the vehicle, where (as he later admitted to an FBI agent) he "made as though he was looking for something." He testified at trial, however, that he was innocently tying down boxes of sneakers he had in the trunk because Valentín had been complaining of the noise while they were driving.

Outside the bar, a group of men were playing dominoes. With his face covered by a bandana, Valentín announced to the group that he was holding them up and that he and his partner would kill anyone who moved. The men put their jewelry and money on the table. Valentín then entered the bar while Miró, also masked and armed with a knife, stood watch over the men outside. Inside, Valentín pulled out a gun and ordered the patrons to give him money. One of the patrons, an off-duty police officer, took out his gun and fired at the robber, hitting Valentín in the abdomen three times. Valentín returned fire, killing the officer.

Upon hearing the shots, Miró raced back to the car. Seconds later, Valentín exited and began to hobble toward the car. There was cross-fire in the street as Valentín shot behind his back at the bar while the owner, using the officer's gun, returned fire. Serrano waited for Valentín to get into the car before he drove off. An eyewitness in a nearby building saw Valentín, with his face still masked, firing his pistol while he limped toward the car. She testified that the car "left fast" as soon as Valentín got in. Serrano claimed at trial that, upon returning to the car, Valentín threatened to kill him unless he drove to a hospital. A tire blew out on the way, so Serrano parked on a nearby street and took a bleeding Valentín out of the car. He then called his mother to pick him up because he didn't have a spare tire.

A police officer who responded to the scene -- and who had already watched security footage of the incident -- heard a radio report of an injured person in a nearby subdivision. He went to investigate and "immediately recognized ... the person who shot" the off-duty officer because he was wearing "the same clothes" and bandana. He radioed a medical emergency, and Valentín was quickly transported to the hospital.

Serrano, meanwhile, had been picked up by his mother. Once home, he gathered his brother and girlfriend to return to his car to fix the tire. Back at the car, Serrano started to clean Valentín's blood off the seats. He found a shirt, a cap, a kerchief, and a small rag, some of which were soaked in blood, and threw it all onto the property of an abandoned house nearby. Serrano's brother was changing the tire when a police officer arrived, recognized the car from the description of the one that sped away from the robbery, and arrested Serrano, his girlfriend, and his brother.

After being Mirandized, Serrano spoke to an FBI agent. During the interview, he told the agent that Miró lived in the Dr. Pila Housing Project. The next day, the police arrested Miró at that address. Serrano later testified at trial that he had never met Miró before that night.

B.

Serrano, Valentín, and Miró were charged with conspiracy to commit a robbery affecting interstate commerce in violation of the Hobbs Act ( 18 U.S.C. § 1951(a) ) and committing the Herol Café robbery ( 18 U.S.C. § 1951(a) ), plus two added counts related to Valentín's gun: first, for discharging a firearm "during and in relation to crimes of violence" ( 18 U.S.C. § 924(c)(1)(A)(iii) ), and second, for causing the death that resulted ( 18 U.S.C. § 924(j) ).¹ Valentín and Miró each pleaded guilty to a reduced version of the charges, but Serrano chose to go to trial. After a 7-day trial, a jury convicted Serrano on all counts.

II.

For purposes of this appeal, there is no dispute that Valentín and Miró committed an armed robbery at a bar during which Valentín shot a patron to death. The principal question in this case is whether the jury properly found Serrano also liable for those acts. To establish that vicarious liability, the government took a two-step approach. First, it charged him with both aiding and abetting the robbery (by serving as the driver) and with conspiring to commit the robbery; second, it secured a so-called Pinkerton instruction, which informed the jury that -- if it found Serrano guilty of the charged conspiracy -- it could also find him guilty of the firearm discharge and resulting death if those acts were both in furtherance of the conspiracy and reasonably foreseeable to Serrano. See Pinkerton v. United States, 328 U.S. 640, 647–48, 66 S.Ct. 1180, 90 L.Ed. 1489 (1946). The jury so found.

Challenging his conviction in toto, Serrano argues that no rational jury could have found that he knew that Valentín and Miró were planning on robbing the bar, hence he could not be liable for aiding and abetting the robbery or for conspiring to commit the robbery. In short, he was an unwitting dupe, not a witting participant. Relatedly, he contends that the Pinkerton instruction should not have been given and that the Pinkerton instruction as given was too imprecise and confusing. Serrano also challenges two evidentiary rulings by the trial court rejecting his effort to introduce exculpatory testimony from Valentín, and he argues that his convictions under sections 924(c) and (j) must be reversed because they may have been premised on acts that are not crimes of violence (as required by statute). Finally, he contends that his 30-year sentence is disproportionate to his co-conspirators' sentences and that, regardless, it is otherwise substantively unreasonable.

A.

We consider first Serrano's contention that there was insufficient evidence to find beyond a reasonable doubt that he was aware of what Valentín and Miró planned to do, much less that he agreed to participate and help them as the driver. "The test is whether, taken as a whole and viewed in the light most favorable to the government, the evidence, and all legitimate inferences to be drawn therefrom, would support a rational trier of fact's finding of guilt beyond a reasonable doubt." United States v. Martinez, 922 F.2d 914, 923 (1st Cir. 1991) (citing Jackson v. Virginia, 443 U.S. 307, 319, 99 S.Ct. 2781, 61 L.Ed.2d 560 (1979) ). Our review is de novo. United States v. Portalla, 496 F.3d 23, 26 (1st Cir. 2007).

Certainly Serrano behaved exactly as he would have had he been part of a three-person group set on committing a robbery. He was with Miró and Valentín before the robbery. He provided the transportation to take them to the bar. He drove by the bar three times. He let his two passengers out of the car up the block -- even though there was plenty of parking closer -- pointing away from the bar. He waited for the masked robbers to return, even after the shooting began. He then served as a get-away driver, speeding off from the scene. And, finally, he tried to cover up evidence of his involvement.

Serrano offered the jury an innocent interpretation of this evidence: Valentín just introduced him to Miró that night, and Serrano took them on a joy ride with no idea that he was assisting them in a robbery, at least until they returned to the car, at which point he claims that he was compelled at gunpoint to drive his passengers away.

While a reasonable juror might have believed Serrano's story, after hearing him testify these jurors did not. And we cannot say that the jurors lacked a basis for finding the government's version of events correct beyond a reasonable doubt. A juror could reasonably have thought it unlikely that Valentín and Miró would depend on an unwitting get-away driver who might act quite unpredictably when the robbery ensued. Plus, why would Serrano stand waiting outside at the trunk of the car while they went to the bar unless he was serving as a lookout and expecting them to return quite quickly? And what did he think the repeated drive-bys were all about? Perhaps most damning is Serrano's contemporaneous statement to an FBI agent that he felt a need to...