Jamie Middlebrook: Guilty on two charges, not guilty on a third.
In prosecutors’ telling, Jamie Middlebrook was a hardened crack dealer who carried a semi-automatic in his jacket pocket, ready to blast anyone on Grand Avenue after his stash. He’d rather be judged by 12 jurors, he said, than carried by six pallbearers.
The evidence from a three-day trial this week, where Middlebrook faced federal gun and drug charges, suggested that the 20-year-old defendant was more small fry than big fish.
New Haven cops arrested Middlebrook by Ferraro’s Market last fall, near a SCCY CPX‑1 9mm pistol that had been discarded in the parking lot and a drawstring bag with 19 grams of weed that had been tied to a fence.
Middlebrook was selling not crack, but leftover marijuana he couldn’t smoke himself. He was selling schwag, the low-grade ganja that a supervisor from the U.S. Drug Enforcement Administration said might as well contain dead bugs and patchy rug.
Middlebrook also loaded the wrong caliber ammunition in his black-and-teal handgun; a New Haven detective said it likely would’ve jammed if he tried to fire it.
Middlebrook’s trial ended Thursday with a verdict that fell short of both sides’ expectations: He faced three drug and gun charges that, combined, could have sent him away for decades. The jury found him guilty of possession with intent to distribute a controlled substance. The jury found him not guilty of possession of a firearm in furtherance of a drug trafficking crime. Middlebrook pleaded guilty to a third charge, unlawful possession of a firearm by a felon.
Did this need to be a federal case in the first place?
The outcome reflected the balance the nation has sought to strike between concerns over gun violence and concerns over incarceration policies that locked up millions of people of color since the 1990s.
How can law enforcement clean up the stretch of the Mill River neighborhood, where residents complain of people defecating in their yards and burglarizing their houses? In this case, as in many others, local and federal authorities worked together to target drug-related gun crimes with charges in federal court, where defendants face far longer sentences than in state court.
Would a tough sentence deter other traffickers from carrying guns? Or would it upend the lives of a small-time pot dealer and his family?
A Chance Run-In
Christopher Peak Photo
664 Grand Ave., near where Middlebrook was first spotted by police.
On the afternoon of Nov. 1, 2019, a plainclothes detective driving around Grand Avenue and Hamilton Street saw Middlebrook standing on a corner by Co-Op Liquor and called out his name: “Jamie!”
Middlebrook backpedaled and took off running through the parking lot of Ferraro’s. One hand swung freely while the other hand stayed in the pocket of his puffy red jacket, as if he were holding something, said Det. Thomas Glynn, who works with the New Haven Police Department’s Shooting Task Force.
Detectives watched him duck down between two cars and drop a gun on the ground behind a black Chevy Silverado pickup truck’s tire. Glynn popped out of their cruiser and stayed with the gun, a loaded SCCY CPX‑1 9mm pistol that he said didn’t have any tread marks on it that would indicate it had been run over.
Det. Joshua Smerecznsky later brought the gun back to police headquarters for ballistic testing. When he pulled the gun’s slide back, two rounds of ammunition fell from the chamber, indicating what he called a “misfeed.” That might’ve been because the gun had been loaded with .380 ammunition, which has the same diameter as a 9mm but with a shorter length.
Smerecznsky added that the gun didn’t have any fingerprints on it. He said that it had been swabbed for DNA, but that the results were still being processed at the state’s crime lab.
After a chase on foot, other cops arrested Middlebrook a few blocks away. He had $373 in cash folded in his pocket, bills that Glynn this week counted before the jury on the stand.
While sitting in the back of a police cruiser, Middlebrook called out to a passerby to get his Proactiv drawstring bag. Officer Brendan Hawley overheard and radioed that to Glynn. He found the bag, right on the fence where Middlebrook had been standing when they first pulled up. Inside, he recovered 19 grams of marijuana, packaged for individual sale as an eighth of an ounce in a couple sandwich bags whose tops had been cut off.
Dad Was Murdered
Middlebrook.
How did Middlebrook end up in trouble?
Middlebrook’s father had been murdered when he was just two years old. In June 2001, his dad was sitting in a car at Shelton Avenue and Munson Street around 1 a.m., when he was shot. Paramedics took him to Yale-New Haven Hospital, but they couldn’t save him.
Middlebrook’s mom calls her son “Sour Patch Kid.” She said he can be aggravatingly tart and lovably sweet.
A former basketball and baseball player, Middlebrook dropped out of Hyde Leadership School in his junior year. He was hyperactive and mouthy; he was often stoned. Visits to psychiatrists, who diagnosed him with post-traumatic stress disorder, didn’t seem to help.
“He started thinking he could handle things on his own,” his mom said.
Middlebrook is “not a bad kid,” his mom said. He donated clothes to homeless shelters. He picked up his cousins from the school bus stop. He planned to get a commercial driver’s license and open up a trucking business with his family.
On his rap sheet, Middlebrook had a state felony conviction for selling crack cocaine in 2018. When he was arrested in this case, he was serving two separate terms of conditional discharges from state convictions.
Just a week before, he wrote on Facebook, “I ain’t perfect but I’m trying believe that.”
The Interview
U.S. District Court
Middlebrook answers questions at police headquarters.
A few hours after his arrest, in a third-floor conference room at the department’s 1 Union Ave. headquarters, Det. Martin Podsiad convinced Middlebrook to waive his Miranda rights and answer questions without a lawyer present.
“What you mean? Like I have to waive them?” Middlebrook asked. “I just want to know what’s going on.”
“You don’t have to answer me at all,” Podsiad said. “I can’t make you talk.”
“You got any juice?” Middlebrook said. “Can I get some weed? Shit.”
Then he spoke to Podsiad, for two hours.
During their interview, Middlebrook admitted he’d found a black gun, wrapped in a hoodie, in a backyard just a few days before. He said it almost felt like a set-up. He said he didn’t know the make of the gun. He said he didn’t even check to see if it was loaded.
“Do I think that you’re a bad person? Do I think Jamie Middlebrook is out there lighting it up?” Podsiad asked at one point. “I honestly don’t. I think that you have a gun, just like I carry a gun. I carry it to protect myself, that’s fine.”
He added later, ““We have yet, during our months of surveillance now, seen you very few times. We don’t really see you street hustling.”
“What do you all see me doing? I don’t do nothing, bro,” Middlebrook said. “I don’t consider myself as a weed man. If I have 14 grams of weed, I know I’m only going to smoke three grams, so I got four more three-gram bags left. Why not sell one? I make damn near half of my money back.”
Middlebrook later said he carried the gun because he’d been robbed in the past and didn’t want it to happen again. “I do the same shit every night. I’m not up here chasing around motherfuckers, worried about who shot who,” Middlebrook said. “I’m not like that. I’m not no shooter. I’m not no jaguar. My father died to a gun so I hate them. I’m from the streets, I know about it.” He added the line he’d rather be judged by 12 jurors than carried out by six pallbearers.
To Federal Court
Armslist
A 9mm semi-automatic pistol.
After the Bureau of Alcohol, Tobacco, Firearms and Explosives got involved, prosecutors transferred Middlebrook’s case to federal court. They charged Middlebrook with using the gun “in furtherance of” a serious crime.
If convicted, he’d face a consecutive five-year mandatory minimum, just for that count.
That added penalty, which applies to only about one-third of federal firearms offenders, results in an average sentence of 12.6 years when added to other charges, according to the U.S. Sentencing Commission. Mandatory minimums for firearms are disproportionately applied to black offenders, whose sentences are 14 months longer on average, the Commission also found.
Middlebrook was looking at that added penalty — at decades in prison — as his trial got underway this week in U.S. District Court Judge Janet Hall’s Church Street courtroom.
In her opening statement, Assistant U.S. Attorney Margaret Donovan quoted Middlebrook’s line about preferring 12 jurors to six pallbearers.
“Ladies and gentlemen, that’s exactly why we’re here today,” she told the jurors.
Middlebrook did not testify at the trial. The jurors did hear him speak at length — in a video of his interview with detectives. (Watch it at the top of this story.)
During a full day of evidence, jurors heard from three New Haven cops who investigated the case and a DEA agent who explained Middlebrook’s slang. They watched security-camera footage of the parking lot from three angles, sometimes frame by frame. They listened to excerpts from the post-arrest interview at police headquarters. And they passed around the baggies of weed and the two-tone gun, now zip-tied and unloaded.
How did it all fit together? Was the pistol part of Middlebrook’s dealing?
During her instructions to the jury after all the testimony, Judge Hall defined “possession-in-furtherance” as having a gun to help “forward, promote or advance” the underlying drug-trafficking crime.
Appellate courts have tried to parse out what that means. Congress even revised the statute after the U.S. Supreme Court overturned the conviction of a dealer who had a gun in the trunk of his car.
Hall told the jurors that drug dealers routinely arm themselves for protection, but this added penalty applies only when they are using the gun in connection with a specific crime. She asked them to consider if the gun “afford[ed] some advantage, actual or potential, real or contingent.”
Two hours into their deliberation, jurors sent out a note: “Do we need to take into account the entire definition of ‘in furtherance’?” it read.
Connecticut Law Tribune
Judge Janet Hall.
Judge Hall said she wasn’t sure exactly what they were asking.
Based on Donovan’s guess that the confusion might be about the phrase “forward, promote or advance,” Hall told the jury that she deliberately used the word “or,” not “and.”
“You don’t have to find all of them,” Hall said. “If you found one of those, that would be sufficient.”
But she reminded them that the concept of “in furtherance” was explained across two full pages, and they needed to consider all of it in making their decision.
An hour later, the jury came back with its verdict. Middlebrook’s family filled the courtroom benches. The lawyers stood. Middlebrook shoved his hands into the pockets of his slate-colored slacks.
The courtroom deputy read off the questions.
Had Middlebrook knowingly possessed marijuana, with the intent to distribute? “We the jury unanimously find the defendant guilty.”
Had Middlebrook knowingly possessed a 9mm pistol? Yes. (Middlebrook, as a felon, formally pleaded guilty to this charge the next morning.)
Had Middlebrook possessed a firearm in furtherance of drug-trafficking? “We the jury unanimously find the defendant not guilty.”
“Is that your verdict, so say you all?” Hall asked, and a dozen jurors all said yes.
In the end, the 12-member jury this week concluded that the “furtherance” charge didn’t fit Middlebrook’s case. Jurors said he had indeed tried to sell marijuana and had carried a gun, but that the two crimes didn’t necessarily go together.
Middlebrook turned to his family — his aunts and cousins, his girlfriend, his siblings, his mother — and stoically tried to hold back the coming sobs. When he couldn’t, Middlebrook turned away. He straightened up and crossed his hands behind his back, readying for the cuffs. The marshals led him out.
Overcharged?
Paul Bass Photo
Defense Attorney Einhorn.
After the case wrapped on Thursday morning, Einhorn argued that Middlebrook was “overcharged.”
The jurors “did the right thing,” Einhorn said. “I think the jury was sending a message to the Justice Department about not overcharging. This is the result: They’re not going to tolerate it. It applies not only in gun and drug cases, but in many other cases, where I think the U.S. Attorney’s Office brings much tougher charges than are necessary under the circumstances.”
Federal prosecutors “have the right; it’s their sole discretion to bring charges,” Einhorn added. “Thankfully, in this case, it was the jury that stood up to the government.”
Tom Carson, a spokesperson for the U.S. Attorney’s Office, said the case was taken to federal court, in coordination with the New Haven Police Department and State’s Attorney’s Office, as a way “to address drug trafficking and associated violence in Fair Haven.”
“We respect the jury’s thoughtful deliberation and its verdict in this case,” he said.
Second Chances
Ferraro’s Market, close to the spot where detectives found a gun.
Judged by 12 or carried by 6: Those outcomes were the only ways Middlebrook pictured his hustle coming to an end. Walled in a cell or boxed in the ground.
Shouldn’t there be another way? How else could Middlebrook account for his law-breaking? What would a more merciful system look like?
“That’s hard to say,” Middlebrook’s mother said. “You kind of wish that there was a way to just give someone a second chance. Allow them to prove themselves, then allow the consequences to come into play. But that’s not the justice system.”
A Fair Haven Heights resident who’s working toward a nursing degree at Gateway Community College, she was seated on a wooden bench in the low-lit hallway outside Judge Hall’s courtroom, her eyes glistening with emotion.
She said she felt relieved by the jury’s verdict, but she also felt stressed by what would happen next: how she’d explain her absence to her employer; where they’d find the money for bond, if he got it; what she’d tell Judge Hall about her son at the sentencing. She said she felt too embarrassed to give her name, saying it wasn’t her “proudest moment” as a parent.
His mother said that she wished the case had stayed in state court, where they would have been “a little more lenient.”
“They wanted more information. They thought he had something about a big fish. He had no information to give them,” she said. “Once they had a situation with that gun, they thought they had a perfect opportunity. They said that in the past: ‘Just tell us this, that and the other, and we’ll make that go away.’”
Especially as recreational pot is being legalized in states across the country — an effort that has stalled in Connecticut — Middlebrook’s mother said it was trying to see her son convicted for selling weed. She said she almost wished she lived in California or Massachusetts.
“No mom wants their child put away in any kind of way,” his mother said. “He’ll be missed. Even down to his little cousins, he’s going to be just missed. I’m grateful I’ll still be able to speak to him: I’m happy he was tried by twelve and not carried by six. But as a mom, there’s disappointment in it.”
This is a tragedy.
250,000 people are reported to have died from opioids in the last 5 years and yet no Sackler from the billionaire class is facing any criminal charge. At most they will part with some of their billions and be left with the rest as they buy their way out of numerous civil suits.<br /> In the meantime, the vicious, racist drug laws from the Nixon administration continue to punish people for something as innocuous as pot. A joint is no more harmful that a glass of wine, but wine is sanctioned and pot (except for medical use) is not. This is irrational.<br /> This young man is being processed into the prison industrial complex even as "liberals" set up re-entry programs and bemoan the loss of voting rights, job opportunities and the stigma of a prison record. <br /> Why is it considered laudatory to work on remediation rather than show some real guts and call for the immediate abolition of all drug laws and the release of all inmates on drug related charges? Are we collectively too ashamed to admit the damage these laws have done to people. Are white people too much in denial as to the racial animus that continues to drive this waste of life and resources?<br /> This young man's conviction is no accident. He was targeted decades ago because of his tribe's political clout. Arrest, convict, take away voting rights and change history. <br /> Whether it's the Republican's reinforcing stereotypes by using Willie Horton to scare everyone or Bill Clinton as Arkansas Governor refusing to stop the execution of a severely retarded black man, the "get tough on crime" crowd never went after the Wall St crimes, but after the easy targets.<br /> Am I the only one sick and tired of watching these pointless arrests and convictions? <br /> Our collective shame and stupidity will be part of history for a long time.