Driver Spotlight: Dre Winston

Sometimes opportunity knocks. Other times, it rolls up on 18 wheels.

Just ask Dre’Shawn Winston (or “Dre” for short).

At 23 years old, Dre was at his lowest point. Financial insecurity left him evicted from his home and dangerously close to losing his car. After three months of unemployment, he took a job as a material handler making less than half of what he had been at his previous employer. One silver lining to his long hours on the docks was that he had a front row seat to a career path he felt could set him up for success: professional truck driving.

There was just one problem: the cost. The closest CDL school would cost Dre upwards of $7,000 to attend and saving that amount was not going to be easy. 

Then one day, Dre was helping to unload a truck driven by DTI driver trainer John Fellers. Dre mentioned that he’d love to be behind the wheel once he could save enough to attend classes. John had a better proposal.

John let Dre know about DTI’s in-house school in Williamsport, Maryland–about an hour from Dre’s residence at the time. Here, Dre could attend classes, earn his CDL, and be guaranteed a high paying job immediately following completion of the course. For Dre, it was a no-brainer.

“If it wasn’t for John, I wouldn’t have gotten to this point to even knowing about DTI and ever since then I’ve been very grateful for that,” he said.

Dre enrolled just as soon as a spot opened up and, though he was the youngest in the course, he saw it was a fit right in from the start.

“In DTI school, it made me a little intimidated but to feel like I’m around others that care and it’s a family-oriented business, it made me feel more comfortable,” he said.

Today, Dre is two years into his driving career with DTI and has no plans of slowing down any time soon. Asked about his favorite aspects of his new life on the road, Dre says the money and the flexible scheduling can’t be beat. He drives a traditional schedule which allows for plenty of home time. In addition, he’s saved enough money to purchase his first home at the age of 25.

Dre’s latest career goal came to fruition this year when he was promoted to driver trainer; a position where he’s able to share his story, his knowledge, and his experience with the DTI’s newest drivers.

“I knew in my heart that I wanted to help others and let them know that I’ve been there and I’m not perfect,” he said. “It has been a blessing to share the knowledge that I do have. For me this is home and I enjoy coming here every day.”