GRAY — Decade after decade, Jay Cushman has invested money, time and even more money chasing an elusive checkered flag at the Oxford 250.

“God’s honest truth?” Cushman said this week from his race shop in Gray. “I went to the Irving 250 in New Brunswick and the CAT 250 at Fredericton and won those. Those were big events, but they were never anywhere near the Oxford 250. I’d have done all this even if the Oxford 250 was held in North Carolina or Canada or Vegas.”

The 50th running of the Oxford 250 is set for Sunday at Oxford Plains Speedway. The annual race, which nets the winner $25,000, attracts teams from near and far. The purse is a big draw, but so, too, is the opportunity to win New England’s most prestigious stock car race.

Perhaps no one has invested more in the Oxford 250 than Cushman. From meager beginnings as a driver with four failed qualifying efforts to fielding cars for some of the region’s most accomplished racers, Cushman has been to every Oxford 250 since 1979 — minus two years in the late 2000s when the Pro All Stars Series held a competing event in Nova Scotia. 

Along the way, Cushman said he’s made a seven-figure investment in the pursuit of an Oxford 250 victory.

On Sunday, Cushman will field his familiar No. 29 car for his son Austin Teras. It will be Cushman’s 40th attempt to win the event.

“It would probably never be topped for him if we could win,” said Teras, 20. “It would be the pinnacle of everything he’s ever done.”

Few could have predicted Cushman would ever be part of Oxford 250 history.

Jay Cushman times laps for his son, Austin Teras, during practice Thursday at Oxford Plains Speedway in Oxford. Daryn Slover/Sun Journal

When Cushman was 12, he was hit by a moving vehicle — a truck and trailer pulling a car out of the pit area — at the Oxford dragway that was on the sprawling Oxford Plains grounds. Cushman was trapped between the vehicles, his leg mangled under the truck’s rolling rear wheel.

Cushman’s father, Joe Cushman, was a national record-holding drag racer at the time, but he immediately swore off motorsports entirely. His business was nearly lost as he focused on Jay’s recovery, which included seven months in a hospital and extensive rehabilitation. Jay’s parents were told he would never walk again.

Jay Cushman, though, had already caught the racing bug.

“When I was 15, I built my first race car,” said Cushman, now 61 and owner of Cushman Competition, a business specializing in performance motorsports engines. “I did it in the back of my dad’s shop, and they didn’t know anything about it. My mother never would have let my father be a part of that. She hated racing, but my dad had drag raced all over the country, and I just fell in love with it.”

Cushman tried to make the Oxford 250 every year as a driver from 1983 through 1986, but he never qualified. 

“We even drew No. 1 for our heat race in two of those, and we still didn’t make it,” Cushman said. “We didn’t know what we were doing.”

Cushman’s failed efforts as a driver turned into a passion for understanding all the parts and pieces of the cars and the engines themselves. He gained notoriety after he built cars for three-time Oxford 250 winner Dave Dion while working for longtime NASCAR Cup Series team Wood Brothers Racing.

When he returned his focus to New England’s Super Late Model scene, he fielded cars for drivers like Oxford 250 winner Larry Gelinas, multi-time Wiscasset Speedway champion Scott Chubbuck, all-time Stafford Motor Speedway win leader Ted Christopher and former NASCAR Cup driver Regan Smith.

Cushman estimates he’s spent well over a million dollars alone on trying to win the Oxford 250.

Austin Teras runs practice laps Thursday in his No. 29 Ford at Oxford Plains Speedway in Oxford. Daryn Slover/Sun Journal

“I spent over $100,000 a year for 10 years at one point, so if my math is correct that’s a million dollars,” Cushman said. “More than that now.”

Chubbuck handed Cushman his best opportunity to win the Oxford 250 in 2004, when he was leading the race with 50 laps to go. While Chubbuck said he simply misjudged his entry into a corner that caused unintentional contact with Dale Shaw in that moment, Cushman recalls a different version of events.

“I made Scott dump Dale Shaw because I felt like I still owed Dale one,” Cushman said. “I thought he’d spin, they’d just black flag (Scott) to the rear, we’d come in and do two tires under that caution and be just fine. … But Dale spun around 360 degrees and kept going, and the caution never came out. Scott got the black flag.”

Those who know Cushman best know how tough that race was to digest.

“It’s all about his passion for that race,” Chubbuck said. “The Oxford 250 has always meant everything to him. He’s spent all the money and all of the effort just to try to win that one race.”

Beyond the Oxford 250, Cushman has impacted Maine’s Super Late Model scene and been a staunch supporter of the division.

In 2006, when then-Oxford Plains Speedway owner Bill Ryan turned the Oxford 250 into a Late Model race, Cushman opposed the change. Cushman even went to Beech Ridge Motor Speedway and tried to work with that track on a package that would boost interest in Super Late Model racing.

Instead of adapting to the changes in racing, Cushman dug in. There are competitive advantages even now with cheaper engine packages available, but Cushman says that racing should always be about engines built by hand, high horsepower and speed.

“Let’s face it, no one is smarter than Jay,” said Trevor Sanborn, who drove for Cushman previously. “He taught me a lot about race cars, about how they work. Jay puts a lot of effort in, there’s no doubt about it — thinking about it, testing, all of that. But Jay can also be stubborn. He doesn’t always want to hear what other people have to say.”

For better or worse, Teras has had to listen to all of Cushman’s advice since he started racing go-karts at 5 years old. And Cushman never made it easy on his son.

“The biggest proud moment for me is I started when he was 5 years old, had four different fake birth certificates so we could race all over the country and he could race older kids,” Cushman said. “You run out of kids classes, you have to go run with adults. As soon as he was in a Legend car, he won races. He won at Beech Ridge before he was old enough to even get in the pits there.

Jay Cushman and his son, Austin Teras, spend time in the pits Thursday at Oxford Plains Speedway in Oxford. Teras will attempt to qualify for Sunday’s Oxford 250 while driving the No. 29 Ford. Daryn Slover/Sun Journal

“But it all made him better. He was always the youngest in any car he got into. We put him in so many situations — Daytona, Vegas, he won all those big pressure events. At 9 years old, he was racing for $100,000. … His mother used to get so mad because I’d run him in classes where he couldn’t win, and I’d say to her, ‘do you want a kid that can win an 8-year old go-kart race when he’s 9, or a 15-year old kid that can win a Super Late Model race?’ “

In 2018, Teras nearly did just that. He led a few laps in the Oxford 250 as a rookie that year, a race eventually won by Georgia native Bubba Pollard.

Teras says Cushman’s approach to racing has helped him immeasurably. This summer Teras won two PASS races and a weekly Super Late Model feature at Oxford Plains, and he enters the 50th Oxford 250 on a short list of candidates capable of winning.

“He’s a perfectionist in all forms of that word,” Teras said of his father. “My mom would videotape all my go-kart races, and we’d watch them back. Even though we’d win the race, he’d tell me 10 things that I did wrong. … It seems hard. It seems tough. But it comes from wanting to win and being competitive. You’re always chasing being better.”

In Sunday’s Oxford 250, the Cushman-owned No. 29 hopes it can be the best among the nearly 70 cars entered.

“I think Jay would tell you he was fine with it if he never won (the Oxford 250), but I bet it would bother him,” Chubbuck said.

“I’ve raced all over the country, but nothing was as big as the Oxford 250,” Cushman added. “It’s everything about it. It’s the best cars, it’s the best of everything, and it’s right in our backyard.”

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