Trucking Careers · Massachusetts · November 10, 2026

Massachusetts Jail Program Trains Inmates to Become Truck Drivers

Illustration of a truck driving instructor and a student at a teal semi-truck on a training yard lined with orange cones — Illustration for this story. Not a photo of a specific location.

Image caption: Illustration: AI-generated illustration, not a photo of the people, vehicles or places in this story. It shows a truck driving instructor and a student at a teal semi-truck on a training yard lined with orange cones.

A jail program in Bristol County, Massachusetts, is training inmates to become truck drivers, and three of them have now earned their commercial driver's licenses, The Boston Globe reported Nov. 9. Six more are pending.

The program is called Road to Reentry Success. Sheriff Paul Heroux launched it to help inmates nearing release land a good job and to lower the chance they end up back behind bars, the Globe reports. "This is a win for taxpayers," said Jonathan McDonnell, director of vocational programs for the Bristol County Sheriff's Office. He said a job as a truck driver provides "a realistic alternative for an individual returning to our community."

How the program works

Heroux got the idea after seeing a commercial driver's license simulator brought to the jail by his predecessor, the paper reports. The simulator helped, but inmates had no way to take classes or practice driving. The sheriff secured a grant from MassSTEP, which funds vocational education programs, to pay for classes, and the state registry gives permit tests at the facility.

Three times a week, the inmate trainees, escorted by two correction officers, go to Amaral Auto and Truck Driving School for classroom work, driving practice and road testing. During training on the road, a sheriff's department cruiser follows the truck.

A first-try pass

Michael Greely, 42, an inmate at the Bristol County House of Correction and Jail, is the trainee the Globe followed through the program. He earned an associate's degree in building construction technology and is a licensed contractor. By mid-September, he was driving rigs around New Bedford with the cruiser behind him.

He also picked up lessons along the way. "Sixth gear is your best friend," he told the paper. "If you miss a gear, sixth gear is always there for you, it will always catch."

On Oct. 27, correction officers woke him at 4:30 a.m. and drove him to Wareham, where a state trooper gave him the road test. He passed. "As soon as I got out of the truck, they came running over," he said of the officers. One gave him a hug. "He told me he loved me, and how big it was for everybody in the department."

So far, Greely is the only one in the program to pass on the first try. "It's really hard," he said. Correction Officer Ron Imbeau called him a model inmate who helped show other trainees how to do the air brakes.

A job waiting

Greely has a truck driving job waiting when he is released, and he hopes to be paroled in January, the paper reports. His cellmate, Shawn Rigo, has earned his Class A permit. "He's a role model to me. If he can do it, I can do it," Rigo said.

For readers curious about the licensing path itself, Big Rig Daily's guide on how to get a CDL step by step walks through the process.