Transition Trucking winner fulfills childhood dream by driving a truck

March 8, 2018

Mark Schremmer


Gregg Softy received the keys to a 2017 Kenworth T680 this past December. He is the second winner of the program that recognizes military veterans who have transitioned into the trucking industry.

Gregg Softy’s fascination with big trucks started at an early age.

“I remember getting a big truck for Christmas when I was 4 years old,” he said.

Softy’s fascination didn’t end there.

As a passenger in his family vehicle, he made a game out of guessing how many trucks he could spot on the trip. As a 6-year-old, he was so enamored with the profession that he would ask the truck drivers at the Vince Lombardi truck stop in New Jersey for autographs.

However, truck driving took a back seat as he attended the U.S. Military Academy at West Point before embarking on a career that included nearly three decades of service in the U.S. Army. Over the years, he was stationed in such places as Germany and Italy. He served in Desert Storm/Desert Shield and deployed to such places as Afghanistan, Iraq, Libya, Haiti, and Kosovo. Softy earned three bronze stars, a Legion of Merit, Defense Meritorious service medal, and many other service and combat badges, decorations and medals.

A couple of years ago, he retired from the military as a lieutenant colonel and decided to fulfill his childhood dream of being a truck driver.

“I was kind of depressed about what I was going to do after the military,” Softy said. “My wife said, ‘you know what you want to do. Let’s make it happen.’ A couple of days later, I turned in my resignation.”

Finally, he was going to get the chance to drive an 18-wheeler.

“I really had no experience with trucks at all. Until I went to CDL training, I had never even seen the inside of a truck. My wife will tell you how excited I was talking to her the day before I got to drive the truck for the first time.”

Since Softy’s entrance into the trucking industry, one dream come true has led to another.

Softy began driving for Stevens Transport and in December was named the winner of Fastport’s 2017 Transition Trucking: Driving for Excellence Award. The second annual award goes to a military veteran who recently began a career as a truck driver. At a ceremony in Washington D.C., Softy received the keys to a 2017 Kenworth T680 Advantage equipped with a fuel-efficient 455-hp Paccar MX-13 engine and a 76-inch sleeper. The truck boasts an approximate value of $160,000.

Softy was chosen out of more than 10,000 applicants.

“It probably took a month before it really set in that I won,” he said.

An owner-operator now, Softy continues to lease on with Stevens, hauling produce, pork, chicken and other refrigerated loads across the country.

Softy’s future plans include upgrading to his dream truck, a Kenworth W900L and going into business with his former co-driver and a fellow veteran of the U.S. Army.

“I’ve always had the dream of getting to drive one of those big monster trucks,” he said. “I’m going to get to drive my dream.”

He and Sean Harding, who was also a top 10 finalist for the Trucking Transition award, plan to launch a trucking company, for which they expect to hire military veterans. The company is named Hell on Wheels after Softy’s unit in Desert Storm.

“We became friends in the military and decided to get into the trucking industry together,” Softy said.

Needless to say, Softy is happy with his decision.

“As an Army officer, I got to see more of the world than most people would see in a lifetime and do some things many people will never get to experience. As a truck driver, I now get to see more of the country I spent a lifetime defending. And I am loving it.”

Editor’s note: Another interesting bit of information about Softy is that he is the step-father of former national champion Clemson football walk-on Brennan Goodnature. Check out the story ESPN wrote about Goodnature in December 2015.


Mark Schremmer, senior editor, joined Land Line in 2015. An award-winning journalist and former assistant news editor at The Topeka Capital-Journal, he brings fresh ideas, solid reporting skills, and more than two decades of journalism experience to our staff.