Judge Grants ​“Sour Patch Kid” A Second Chance

Jamie Middlebrook is headed not to prison but to his mother’s house for a 14-day quarantine, and then a stay in a rehab facility — assuming one can be found amid a pandemic.

That was the result of a federal sentencing that took place Monday over the Zoom teleconferencing app.

U.S. District Judge Janet Hall was sentencing Middlebrook for selling marijuana and another for possessing a firearm as a felon.

Middlebrook faced a potential three-year prison sentence, a six-figure fine, and one to three years of supervised release. That sentence might have shown him the seriousness of his crimes, driven home the point that he must not commit them again, and kept a dangerous criminal off the streets. Or it might have pushed a kid who grew up surrounded by crime, without a father, and who made a series of stupid decisions to become a hardened criminal and do worse once released from prison.

Hall opted for another option, that, if Middlebrook can rise to the occasion, will allow the 21 year old to finish high school and get a job. She gave him a sentence of time served, with a supervised release of four years, part of it in a rehab facility.

In January, Middlebrook was convicted of possession with intent to distribute a controlled substance, and pleaded guilty to a charge of possession of a firearm by a felon. A jury found him not guilty of a third charge that would have sent him to prison for at least five years: using a gun in furtherance of selling drugs. (Click here to read more about the case and Middlebrook’s life story.)

The trial exposed the difficulties of the young man’s upbringing that led to the November afternoon when he ran through the Ferraro’s parking lot trying to escape the police, hid a pistol under a truck’s tire, and left behind a bag of individually packaged marijuana he had intended to sell.

His father was murdered when he was 2. His mother had to work and take classes at Gateway Community College at the same time, meaning she didn’t have enough time to look after him as she might have liked. He grew up surrounded by crime, and without a male figure to steer him away from it.

Yet he also has positive forces that might allow him to succeed once he leaves a rehab program and starts a new life. He has a loving family and a dedicated mother. He did well in school, when he was in it. He excelled at math, and used to win awards for it.

“It kind of hurts my heart to know that he has gotten himself in trouble,” his mother said at his sentencing on Monday. ​“He’s actually a sour patch kid. And I honestly believe in the bottom of my heart that if given another chance he could” get his life together, finish high school, and get a job.

After Hall’s decision, Middlebrook will get that chance. As soon as he can get a signed order, he will be released from Donald W. Wyatt Detention Facility in Rhode Island where he is currently held, and he will return to his mother’s house in Fair Haven Heights for a 14-day quarantine after potential exposure to Covid-19. He will stay with his mother until he is admitted to a rehab facility, and will not be able to leave the house. Hall said she would direct his placement to Trinity Glen Men’s Program in Sharon because it is still accepting new clients, and has said it could take Middlebrook within 30 days.

He will then spend up to nine months in an inpatient rehab facility, after which he will serve four years of supervised release. During that time, he must participate in an educational program to get his high school diploma or GED, work, and/or volunteer, with those activities totaling 35 hours a week.

Saving Mr. Middlebrook

Middlebrook’s offenses and his criminal history carried a guideline sentence of 33 to 41 months in prison, a fine of between $10,000 and $100,000, and one to three years of supervised release. Those guidelines were not required, but were simply a recommendation of a sentence based on a score generated by Middlebrook’s offenses and his criminal history.

Before the trial, the prosecution submitted a memo requesting that the judge issue a sentence at the upper level of the 33 – 41-month range with a supervised release of three years and no fine.

Defense Attorney Jonathan Einhorn asked the court on the behalf of his client for a sentence of time served and a supervised release, with part of it in a rehab facility.

Hall first accepted the prosecution’s characterization of Middlebrook’s offense level, with the guideline sentence of 33 – 41 months. Einhorn requested that she reduce the offense level by two notches, which would have brought the guideline sentence range to 27 – 33 months. Hall did not accept that request.

After listening to Assistant U.S. Attorney Maria Del Pilar Gonzalez make the government’s case, Einhorn began a short appeal for leniency with a description of his client. ​“Mr. Middlebrook is a kid,” he said. He’s 21 years old. His mother, who was watching the proceedings, is terrific, he said, but had to raise him by herself while working and going to school. He then began to talk about Middlebrook’s father when the technical challenges of a virtual court proceeding cut him short.

“You’ve done something to your mic, Mr. Einhorn,” Hall interrupted after the attorney’s impassioned defense became an indecipherable jumble of electronic mumbling. ​“It’s like you’re speaking under water.”

Einhorn repositioned himself and resumed. His client does have a criminal history, he said, but for relatively minor offenses. ​“I’d like to be a part of saving Jamie Middlebrook,” he said.

You say he’s ready to be saved, said Hall, but ​“how do we know that?” she asked. He got lucky and walked away with light sentences for offenses in the past. ​“And here he is again not that long after. He didn’t get it.” He’s still young, she added, and will continue to make stupid mistakes.

Spending time in jail does not help anybody, Einhorn replied. Middlebrook needs help with his addiction, he said. ​“At least if he’s got the addiction under control and he’s got some tools, he’s safer and we’re all better off.” If he spends more time in jail, he said, he’ll come back ​“a more accomplished criminal.”

Sitting in his prison cell, with a white painted cinder-block wall behind him, Middlebrook made his own case. ​“My being here doesn’t help me at all,” he said. ​“I want to prove that I can be out there and get my life together.”

Middlebrook participated briefly in a rehab program after his conviction through the Salvation Army. He said it helped him.

“I never was no bad kid or whatever. I just got caught up in stupid things. I think that was from me not having a male figure… I never had a chance to even see any different type of lifestyle.”

If she released him to a rehab facility, it would be his last shot, Hall told him. ​“That’s your chance. And if you mess that chance up, you are going to go to jail,” she said.

“Yes, your honor,” he replied.

Hall then turned, figuratively, to the prosecution.

He says he has not been given a chance, said Gonzalez. ​“I would say that quite the opposite is the case.”

He had a track record of getting arrested, getting charges dropped or receiving lenient sentences, and then ​“it was a month, a week, three months before he was arrested again,” she said. ​“It’s immaturity, but it’s also a blatant disregard for the court, the rule of law… and it’s dangerous. All the breaks that he’s been given have not served him and have not served the community.”

The prosecution’s sentencing memo included a full review of his criminal history. At the time of his arrest in November, he had two other cases pending, was serving two terms of conditional discharge, and had already been arrested ten times since turning 18. He was 20 at the time. In most of those cases, he was arrested for drug charges or for interfering with the police. Many charges were dropped, and for those that were not he received suspended sentences.

“I think a period of incarceration would send a real clear message to him that this is serious,” Gonzalez said. ​“It might not be as serious as the violation of the person in the cell next to him, but this is serious.”

Hall then launched into her decision. ​“He’s still, I hate to use the expression, but a kid,” she said. ​“I struggle with the idea [that] locking him up for three years is going to really put him in a better place to not be a danger to the community.”

She outlined the factors that she was weighing as she made her decision. First, there was the seriousness of the offense. ​“The fact that he wanted to walk around New Haven with a gun in his hand is a very serious crime,” she said. ​“Just having the gun makes him an agent for violence on the street.”

She acknowledged that he had walked out of sentencing hearings before and gone right back to his old habits. ​“I wouldn’t question your honesty today,” she said. ​“But the question is how long will that resolve last.” Will he go right back to Farnam Courts and start dealing drugs again, or will he get a job and go back to school, she asked? ​“Because if it’s the former, then I should lock you up, because then at least I’ll save New Haven from you.”

But Middlebrook had not really benefitted from any programming, she said. He appeared to be a low-level street dealer who had just been caught a bunch of times.

“Lastly I have to provide you with care and treatment in the most effective way,” she said.

And on top of everything, there was his age. Middlebrook was one of the youngest defendants Hall had ever had, she said.

She asked how long he had been incarcerated already.

Middlebrook said he’s been locked up since Nov. 15: five months.

Then, Hall handed out his sentence. Those five months would constitute his time served. Next, he goes to a rehab facility and once he’s out will continue school, find work, and do community service.

“I have a hope that with the right programming, Mr. Middlebrook can change his life,” Hall said. If she were in a court room, she likely would have turned to the defendant to say the next piece staring directly at him. But her courtroom consisted of a few boxes on a computer screen, so she just continued looking forward as she was already doing.

“If I’ve made a mis-judgement, then we’ll be back. I hope not.”