Robert Short fired a single bullet into his childhood best friend’s head and left the body in a darkened stairwell. Short then walked out of the building with the victim’s baseball cap on his head and called up two mutual friends, asking help to find their buddy who’d gone “missing.”
The story of that betrayal emerged in federal court on Church Street Wednesday at the day-long sentencing of two Red Side Guerrilla Brims gang members who terrorized New Haven during a blood-soaked span from 2011 to 2013.
In statements from eight people whose relatives were gunned down by the gang, witnesses described a 10-block section of the city ripped apart by drug dealing.
U.S. District Court Judge Janet Hall sentenced Short to 30 years in prison for causing a death through a firearm and sentenced Jeffrey Benton to 40 years in prison for engaging in racketeering activity, money laundering and conspiracy to distribute 280 grams of crack. After their release, both defendants will have an additional five years of supervised probation, including the first six months under house arrest.
But first, the judge and lawyers and relatives on both sides of the case spent hours recounting the toll that the drug- and gun-dealing gang exacted on New Haven.
The testimony revealed that it’s not only addicts who are harmed by the illegal substances that gang members sling, but also the friends who have to stay up on the ever-shifting rivalries that can divide friend and families, sometimes fatally.
“I’ve sent a very large number of people who were drug dealers to prison. I knew they were very serious because of the damage that drug dealing does to people, their families and their communities, even if they didn’t pick up a gun,” Judge Hall, a Clinton appointee, said before delivering the sentence. “This is the life of a drug dealer: You’re facing terrible consequences, and you’ve wrecked a tremendous amount. You’ve destroyed your community.” She continued, “Your case, unfortunately, is an outstanding example of what I’ve been trying to say all these years.”
The Red Side Guerilla Brims ran a trafficking loop with Bangor, Me., smuggling manufactured crack-cocaine north and illegal guns back south to the Elm City. As part of a plea deal accepted Wednesday, two Brims admitted their involvement in the murder of four people, including Short’s childhood friend Darrick Cooper, and an attempt to kill a fifth.
“It’s overwhelming to me, as I read all the [pre-sentencing reports] and heard from the people who spoke today. It’s so senseless, so unspeakable. I can’t articulate the degree of harm that you’ve caused,” Hall said. “Somebody made a comment, ‘This is where we live, this is our life.’ You’re hit by a stray bullet or you’re targeted by gang members. Didn’t you think about all the people’s daughters and sons who live in the neighborhood, whenever you pulled a gun out to start shooting? It’s a level of violence, in my 20 years, that I’ve never seen.”
Building A Criminal Enterprise
According to the gang’s lore, the Brims organized on the East Coast within New York’s state prisons around 1995, as an off-shoot of the Bloods street gang. Members share a secret language of hand signals and code words, swear an oath to retaliate against snitches, and participate in an initiation ritual that involves a 59-second assault by the group.
According to federal prosecutors, a New Haven faction formed in late 2010 when two boys broke away from another Bloods sect and started recruiting for a new gang. Calling himself “Tall Man,” Benton, now 32, emerged as the gang’s leader, because of “his willingness to commit armed robberies and shootings,” prosecutors wrote in a memo.
The Brims differed from other local gangs in their brutality and their ambitions. While other crews tagged their names in graffiti and boasted on social media, the Brims weren’t widely known, preferring to keep a low profile — except to rival drug-dealers whom they’d regularly hold up. 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 geography. They were based in Edgewood, with headquarters at 303 Norton St., between Whalley Avenue and Goffe Terrace, but their true sights were set on an interstate trafficking network.
Under Benton’s leadership, the Brims set up a circuit between New Haven and Bangor, where Benton’s cousin lived. The gang pulled in a higher profit margin on the crack-cocaine sold in Maine: about $6,000 per 50-gram shipment, double the going rate in New Haven. Rodrigo Ramirez, the gang’s distributor in Bangor (who’d been forced into hiding there after retaliation for his involvement in a botched robbery) wired at least $50,000 directly to Brims members, plus more cash to relatives.
Then, through straw purchases from a gun dealership or in trades with addicts, the gang also ran firearms back to New Haven. The pipeline gave the Brims “easy access to handguns and a steady flow of money,” prosecutors said.
Starting in January 2014, as part of “Operation Red Side,” undercover drug buys and firearms seizures by New Haven police and federal ATF agents cracked open the gang’s operations. (Project Longevity — the partnership in which federal, state and local law enforcement work closely to identify gang members responsible for shootings, give them a chance to go straight, then pursue long federal sentences if violence continues — played a big role in that investigation.) All 21 of the Brims members indicted in the operation have since pleaded guilty.
But that came too late to stop the seven murders — including that of Darrick Cooper — that prosecutors have charged Brims members with committing.
Short, now 30 years old, goes by the nickname “Santana.” His mother was a drug addict who was murdered before she turned 40 years old. Families like the Coopers took him in. For a while, that lifelong trust protected both Short and Cooper from gunfire.
Cooper, also known as “Markie D,” was a leader of the rival Grape Street Crips gang and gave the go-ahead during the summer of 2011 for his members to rob Bloods sects, like the Brims, at gunpoint. After another gang killed off one of Cooper’s robbers, all the Bloods sects held a universal meeting to discuss what to do. The Brims subsequently took it upon themselves to kill Cooper.
Short tried to warn his best friend that a hit was coming. Cooper then reached out to Benton and other gang members to discuss the fact that he was on the “food” list. Even though other Brims had also tipped Cooper off, Short got all the blame. He was told to kill Cooper or be marked as “food” too. It was “kill or be killed,” as Short’s defense attorney phrased it.
Early on Sept. 19, 2011, Cooper and Short partied together. Around 1 a.m., Cooper’s girlfriend asked for a ride, but Cooper said he was getting “pinged up” on cocaine and would call her back soon. Short had taken him to an abandoned building on Goodrich Street in Hamden, where his old girlfriend used to live. Cooper flashed a .32-caliber handgun, telling Short he had to protect himself.
At a certain point, the pair got out of a car and walked around the back of the house, up to the second-floor unit. Short lodged a single bullet into the back of Cooper’s head. He returned to the car with Short’s baseball cap on his head and Cooper’s gun.
After the murder, Short called up Cooper’s current girlfriend and another Brims member who was close with him. He said that they’d done coke together and that Cooper wandered toward a housing project. Now, Short said, he couldn’t find his friend and asked for help to go look for him
The next day, he rang Shana Moseley, Cooper’s ex and the mother of his only son. Short gave her the location of the body. “The nerve of you,” Moseley said on Wednesday. “You’ve been at my table. I told you to take showers, I washed your clothes. He was something I needed, and you know I needed it. I never felt weak in a way you made me feel.”
Cops soon booked him for possessing two firearms.
Now, as Short pleaded guilty to killing his best friend, Donna Santiago, Cooper’s mother-in-law, said she hoped that Short suffers. “You slept in my daughter’s house. My nephew was calling you uncle, and you played games with him. For you to take his daddy from him, you’ll pay, brother. I hope it eats your mind up,” she said. “You have the same tattoos on your hands, and you betrayed him. You are a coward. You couldn’t even look him in the eyes before your turned on him. Snake, you stooped so low. You took people who entrusted you and messed with their lives. You have hurt your family and friends.”
For that, she said, “I hope they send you to the farthest spot, to Colorado or California, so your people and your daughter can’t see you. I hope they send you far away from your family, just so you know what it is like. May God have mercy on your soul, but I hope our system doesn’t.”
Santiago said Short and Benton’s drug-dealing and gun-wielding embodied a “lost generation who don’t care about nothing.”
“You don’t want a future. You want to run the streets, you want to sling like you’re in the saloon,” she said. “What for?” She said her final revenge against Short will be raising Cooper’s son into the man Short should have been. “My grandson is going to grow up being someone. He’s going to get a college education,” she said. “He’s going to show you how to live.”
In taking a plea, Benton, 32, meanwhile, admitted that he played a direct role in at least four more killings, either pulling the trigger himself or directing another gang member to do so.
Among his known victims were Kevin Lee, a marijuana dealer who was shot three times in a botched robbery in April 2011, and Donald Bolden, the gang’s contact with higher-ups in New York who was gunned down in March 2012.
Benton also ordered an attempted murder in February 2011. In a hit job for his coke supplier, he asked an associate to kill someone. But Benton picked out the wrong target, mistaking Carl William for his brothers. Only one shot hit Williams (in the big toe of his right foot), and he survived.
But the victim that prosecutors highlighted on Wednesday was Donell Allick, a star basketball player that Benton shot through an open window.
On June 24, 2011, Benton had gone out to Beaver Hills with three other Brims to track down Cooper, thinking he was at a party nearby. Unable to find him, they heard Allick’s voice echoing from a nearby townhouse. Benton was angry because Allick — kicked off Providence College’s basketball team after a drug conviction in 2006 — had recently sold him a 150-gram batch of bad cocaine.
“[Benton] may be the first person I know to dislike him. I never met anyone that had a problem with Donell until recently [during the case], and it’s mind-blowing to me,” said sister Daia Allick, who credited her older brother with being her inspiration to go to college.
The gang members crept up to the kitchen window, where they could see that Allick stood in a doorway chatting with two girls in the next room over. Benton and another Brim argued over who’d get to kill Allick. The other gang member wanted to shoot, but Benton won out because his .357-caliber revolver wouldn’t drop any shell casings. He popped six shots through the open window into Allick’s back, three of which hit him in the torso.
Back in the car, Benton and the others joked around about the murder. Benton mimicked the sound that Allick had made each time he was struck with a bullet. He later buried the gun in his backyard.
Police responded to the shooting around 1:50 a.m. and found Allick in a pool of blood. The case would go cold for years, with detectives thinking Allick had been killed because of his association with Cooper.
Allick died around 5:30 a.m. that morning. In the hospital, Allick’s son stood at the bedside and rubbed his father’s arm. Crying, he begged his father to wake up. “‘I’m gonna be good in school. Please, dad, wake up,’” his grandmother, Valerie Barber, recalled the boy saying. “It tore his mind apart,” she said.
Like Short’s betrayal of Cooper, Benton knew that he was about to take out someone he was closely connected to. His own brothers were tight with the victim’s family, particularly Allick’s sister Theresa Barber.
“These are not strangers; these are not people I didn’t know. If I go through my cell phone, all of their numbers would probably still be in there,” Theresa Barber said, at one point Wednesday. “We still love you. You was one of us, and you took one of us. How do you come back from that?”
She continued, “I had to go to therapy because there were days I would sit in bed and I couldn’t move. Imagine everyone in your circle dying, every last person plucked off the earth. How do I go back to telling somebody who I don’t know everything from these years of my life and expect sympathy? ‘Did you grow up with a bunch of murderers?’” she imitated her therapist asking. “I gotta ride by Evergreen and blow a kiss at his tombstone. That’s how I see my brother. And my mother, she’s a strong woman: She rides by that cemetery every day on her way to work or town, every single day,” she said. “What y’all did to my mother — y’all gonna rot. You ain’t gonna rot in hell, right here on earth.”
Still, Theresa ended by saying, “My only question is why, and it might never be answered. I say this: I still love you, because I know better and because you did something wrong and because Donell taught me loyalty every day. God bless.”
After hearing that, Hall pointed out the particular cowardice, amidst “all the toughness of street life,” of taking aim at Allick, this family friend, when his back was turned. “It sounds to me like you must have been stone cold,” she said.
“How You Ended Up Here”
But before Hall handed down the sentence, defense attorney Francis O’Reilly said that Benton’s rough childhood had to be considered.
Hall agreed. “I think I understand how you ended up here,” she told Benton, based on reviewing his files.
According to a pre-sentencing report, prepared by Benton’s defense attorney Bruce Koffsky, Benton was born into this world without any care.
His 19-year-old mother, Patricia Benton, didn’t take him to a prenatal checkup until she was six months pregnant, describing the baby to doctors as “unexpected and unwanted.” The father, one of four men that impregnated Patricia with five kids, was a life-long drug addict who sold crack and pimped women. Benton didn’t find out about him until he was four years old, after the father died from heroin overdose.
His early years were spent in a squalid apartment on Orchard Street. Food was always in short supply: Benton’s siblings described meals of syrup sandwiches — when there was anything in the cabinets to eat at all.
Patricia said she was “too friendly” and allowed dealers to sell and stash drugs at the place. The activity drew gunfire to the house, and Benton learned at an early age to dive away from the windows if they heard shots. Often, he’d sleep on the floor.
In September 1990, when he was five years old, Benton went to the emergency room at Yale-New Haven Hospital because his penis was swollen and discharging puss. Patricia claimed a sibling kicked Benton, but a positive gonorrhea test revealed he’d been sexually assaulted. Benton told a doctor that his uncle, who lived in the apartment, “squeezes his ‘birdie’ and pulls it,” according to medical records. Patricia had “no affect” when told: “She remained flat and had no explanation,” the report continued. She vowed to confront the uncle, but the nurse doubted she’d follow through.
The Department of Children and Families followed up the next day, and Benton described being sodomized by his uncle in greater detail. On a phone call with DCF, Patricia said she “knows her brother and he couldn’t do those things,” according to an investigator’s writeup. But after the uncle was arrested, DCF closed the case.
Benton’s family would shuffle between more than a dozen houses after that. At nine years old, in Newhallville, his friend was shot in the face and killed while they were outside playing football. Benton said he still recalls going to the funeral and not being allowed to approach the open casket. At another house in the Hill, the next year, an anonymous tip said that Patricia was using and selling crack. Cops showed up and arrested Patricia’s boyfriend and oldest son, but they left the other kids with their mom. Back in Newhallville, a fire destroyed all the family’s possessions. More calls were made to DCF, and Benton witnessed another death, after a neighbor drowned from jumping off a pier near the Sound School.
At age 11, Benton committed his first crime, attempting to steal a car. His probation officer wrote that Benton “does not have a chance for rehabilitation if mother continues her substance abuse activity.” By age 13, he started smoking marijuana five times a day. His mother kept him out of counseling, so he wouldn’t have to “relive sexual abuse,” a DCF report said. At age 14, he was hospitalized for expressing suicidal thoughts.
“It is not a stretch to say that Jeffrey Benton’s life was destroyed by the time he was 8 years old,” Koffsky wrote in his memo. “Gang activity, with its focus on criminal behavior, is where he found validity, escape from a miserable life, camaraderie and loyalty.”
“Everyone failed you,” the judge concurred. “As a child, you’re not expected to make that right,” Hall told Benton. That didn’t excuse the behavior, she clarified, but “there’s no question that you’re in front of me today because of your childhood and what you confronted.”
Still, Hall noted, “I would think you, of all people, would have understood what drug dealing can do,” given how it had torn up his family.
The victims argued that was giving Benton too much leeway. In their statements, they repeatedly pointed out that they’d grown up in the same neighborhood, suffered the same indignities. It’s about choices one makes, not the circumstances themselves, they said, urging the maximum punishment.
A Long Sentence
Given the corpses the Brims left behind, federal prosecutors could have sought the death penalty. But they decided to take that option off the table, given the tough upbringings that the killers faced.
In accepting a plea deal, both Benton and Short escaped life sentence that federal sentencing guidelines recommended and that several family members of the victims wanted.
Still, the defense attorneys requested the minimum.
The lawyers pushed for the lowest sentence allowed by the plea agreement: 30 years. And they asked the judge to credit the time Benton and Short had each served for prior convictions: five years that Benton spent in federal lockup on a heroin distribution charge, and six years Short had spent for unlawfully possessing two guns, the weapons he’d switched out to throw off the investigation into Cooper’s murder.
The defense attorneys argued that a full sentence would mean the men would be effectively punished twice for the same gang-related activity. “It’s intertwined so completely that I find it difficult that the court doesn’t see it,” said O’Reilly, Benton’s counsel. “To slice out one with another is not to look at the real-world facts with what goes on in these enterprises.”
Hall rejected that argument. The mere fact that the prior offenses were both committed in New Haven around the same time wasn’t an excuse for leniency, she said.
After reading the sentences, Hall had the same final word for both defendants. “You’re going to be a lot older when you’re released. You’ve been sitting in jail for a long time already, and you’re going to be sitting there for a lot longer,” she said. “I hope you can find a way to live a constructive life in there.”