“Chewie” Killed, Then Struck A Deal

After murdering four people, should a gang’s enforcer receive a lighter sentence for turning in other members who participated in the bloodshed?

U.S. District Court Judge Janet C. Hall was faced with that dilemma Wednesday in her Church Street courtroom as she weighed the fate of a killer who turned the tables on one of New Haven’s deadly Red Side Guerrilla Brims.

Lawyers and victims offered different takes on how much time a gangbanger deserves for participating in six shootings, then helping authorities lock up others who’d carried out the violence.

“I am charged with the task of somehow balancing the enormity of pain and loss that you caused by your actions with the tremendous assistance — almost unparalleled — that you provided to law enforcement,” Hall said. ​“The problem is when I use the word ​‘balance.’ There is no way to ​‘balance’ those two things, and that’s when my shortcomings as a human being will be evidenced to you, the prosecutors and the victims.”

Leading up to the judge’s decision, Luis ​“Chewie” Padilla, 25, admitted to narcotics trafficking and related acts of violence, including murder, attempted murder, assaults and armed robberies. He committed most of the crimes as enforcer for the Red Side Guerrilla Brims, an offshoot of the Bloods street gang, who terrorized New Haven from 2011 to 2013. Padilla shot at innocent bystanders, organized hits on disloyal members, robbed other gangs’ stashes, and held down a trafficking network that ran drugs and guns across state lines.

Padilla appeared before Judge Hall on Wednesday in a black polo shirt, pulled over a long-sleeved prison uniform. In a quiet voice, flat of affect, he read a short statement to the court.

“Please believe me when I say I’m sorry. I’ve suffered every day knowing how much pain I caused,” he said. ​“After my arrest, I had the choice of bringing forth justice. I chose to do right.”

After weighing the brutality of what she called an ​“indescribable reign of terror,” Judge Hall gave Padilla an 18-year sentence.

That punishment tripled what the defense had requested. But it still came in far below the life sentence recommended by federal law.

Federal prisoners are required to serve at least 85 percent of their prison term and are not eligible for parole. After he’s released, Hall ordered, Padilla will also have five more years of probation.

All Business

Padilla’s sentencing closes a multi-year, multi-agency investigation that took down 21 former members of the Red Side Guerrilla Brims. A joint undercover investigation of the ATF and the New Haven Police Department, known as ​“Operation Red Side”, which began in January 2014.

The investigation revealed that the Red Side Guerrilla Brims arrived in New Haven in late 2010, when two boys broke away from another Bloods sect and started recruiting. Calling himself ​“Tall Man,” Jeffrey Benton, now 33, emerged as the gang’s leader.

The Brims differed from other local street gangs in their brutality and their ambitions. While other crews made their names known with spray paint and online posts, the Brims kept a low profile. And while other gangs tended to represent neighborhoods (like R2 in Newhallville or the Grape Street Crips in the Hill), the Brims didn’t care about local turf.

They were working on establishing on an interstate trafficking network, prosecutors said. The Brims traded crack-cocaine for illegal guns in Bangor, Me., where Benton’s cousin lived. The gang pulled in a higher profit margin on the rocks, earning about $6,000 per 50-gram shipment, double the going rate in New Haven. Then, through straw purchases from a gun dealership and trades with addicts, the gang ran firearms back to New Haven.

The pipeline gave the Brims ​“easy access to handguns and a steady flow of money,” prosecutors said. Padilla travelled to Maine for the operation several times, they added.

Authorities learned that directly from Padilla, Assistant U.S. Attorney Peter Markle noted in court on Wednesday.

Eight months into their crackdown, law enforcement placed Padilla in federal custody, after a gun was found in his home. Since then, Padilla had been cooperating with the government’s case against the Brims. He described the gang’s hierarchy, its rules and its profits, and he identified members. He admitted his own culpability in court on Sept. 29, 2015, pleading guilty to three charges.

“He broke allegiances and provided detailed and compelling information to law enforcement,” Markle told Judge Hall. ​“His cooperation was forthright and steadfast. He never wavered.”

In total, with Padilla’s help, the investigation resolved seven murder cases, four attempted murders and four armed robberies that occurred in 2011 and 2012, plus one earlier homicide that had almost gone cold.

Victims’ Families Dubious

The victims’ families who packed the courtroom benches on Wednesday questioned what had motivated Padilla to turn state’s witness. Had he shown any genuine remorse for gunning down their loved ones? Or was he was simply trying to protect himself from life behind bars?

Robert Kappes, the defense attorney, said the extent of Padilla’s cooperation revealed how sorry he was for his actions. He said his client admitted to crimes that the police didn’t even know about, and he risked his life by taking the witness stand in state court to testify for prosecutors.

Padilla began killing when he was just 16 years old. He claimed his first victim on March 14, 2009, when he shot and killed Thomas ​“Tank” Daniels, Jr., an 18-year-old a recent graduate from Wilbur Cross High School who was enrolled at Gateway Community College, during a failed robbery attempt in the Hill.

Padilla didn’t publicly own up to that crime for eight years, leaving family members unsure who’d killed the teenage boy until March 16, 2017, when they received a last-minute call that Padilla planned to plead guilty.

Tank’s dad, also named Thomas Daniels, said he missed playing chess and video games, coaching the baseball and basketball team with his son. He said he’s suffered from post-traumatic stress disorder ​“real bad” ever since. He has tried to work through the trauma by founding a support group for other dads who’ve lost children to violence, Fathers Cry Too.

“This murder took everything from me: my son, my best friend, my main motivation,” said Daniels. ​“I’m still recovering. I’m here today so my son could get some justice.”

After he spoke, Judge Hall asked if Padilla’s confession had helped bring him closure.

“Was it a comfort to know how your son died, who killed him?” she asked.

“No, not at all, because it’s after the fact,” Daniels said. ​“He’s helping himself.”

Daniels later added that Padilla would serve in prison for just as long as his son was alive. ​“That number alone is an insult,” he said. “[Tank] is gone for eternity.”

His Next Victims

After joining the Brims, Padilla orchestrated a killing spree to which he also fessed up.

During three bloody months in 2011, he played a role in the murder of Derrick Suggs, an innocent bystander, on March 18; Kevin Lee, a marijuana dealer who was shot three times in a botched robbery, on April 20, and Donnell Allick, a star basketball player that Benton, the gang’s leader, shot through an open window in Beaver Hills, on June 24. 

“I don’t want him to ever see the light of day again, because it’s not fair to those who have lost,” said Derricka Suggs-Wilkes, whose father was killed.

Padilla also admitted to shooting and wounding people in New Haven on Feb. 23 and March 29, 2011. He said that he also participated in a home invasion on Putnam Street on May 30, 2012. 

Kappes, the defense attorney, initially asked Hall for a six-year prison sentence, arguing that Padilla had taken a significant risk by cooperating with law enforcement.

“The threats of violence, threats of retaliation, threats of death are going to be with Mr. Padilla for the rest of his life. Any number of his former gang, if they find him, will assault him or kill him, and any rival gang would assault and kill him. Any time Mr. Padilla meets someone unknown, fear and paranoia will go through him,” Kappes said. ​“He lies prostrate before the victims in this case, before the court and before society. Mr. Padilla is haunted every waking moment and every sleeping moment by the souls of the victims in these cases. That’s a prison that Mr. Padilla will live in for the rest of his life.”

The government’s lawyers called that recommendation ​“strikingly low.” But they added that Padilla’s cooperation had been indispensable to convicting the other Brims. In a long speech, Markle described some of the information Padilla had provided, and he detailed even more for Judge Hall in a private memo that remains sealed.

“[Padilla] left a trail of destruction and a trail of grief. He shot at people too many times to count, fortunately missing some and tragically wounding many,” Markle said. ​“But without his cooperation, a number of violent crimes would have gone unsolved and a number of defendants would have avoided prosecution. With his cooperation, we do have some closure and some justice. With it comes the dilemma of determining an appropriate sentence.”

“Murder Capital”

Judge Hall said she had never heard a lawyer stick up for an informant as Markle had, and she agreed that Padilla’s cooperation had been ​“significant” and ​“substantial.” But after hearing from so many victims of the gang’s violence in one sentencing after another, she said that she had trouble squaring how his cooperation could make up for so many killings.

“I can’t understand how a 16-year-old or an 18-year-old or even a 25-year-old goes out and just starts shooting,” she said. During 2011, ​“it felt like almost every week I would wake up, and the headline on the New Haven Register would be another shooting, another person dead, another attempted murder or robbery. It just kept going. I think we became the murder capital of America.”

After she took a five-minute break, Hall handed down the 18-year sentence. She said that Padilla could write to the victims’ families, as one mom had requested he do every week as a reminder of her constant pain.

“The sentence doesn’t begin to impose the seriousness of what you did,” Hall said. ​“I would just ask, in the days ahead, in the years you will be incarcerated, that you come to some sense of understanding of what pain you caused. You can change. You still have your life.”