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DiBenedetto Hopes To Hit Cup Series Victory Jackpot after Big Career Gamble

Note: This continues a series of feature stories highlighting competitors in the Big Machine Vodka 400 at the Brickyard Powered by Florida Georgia Line at the Indianapolis Motor Speedway on Sunday, July 5. Stories will appear on IMS.com every Wednesday.

In 2018, Matt DiBenedetto placed a bet on himself when he left the Go Fas Racing No. 32 team with no prospects in sight. He called it “a leap of faith.”

So, it’s fitting that DiBenedetto began to reap the rewards in Las Vegas last weekend with a second-place finish in the Pennzoil 400 at Las Vegas Motor Speedway.

“This is beyond where I could have imagined where I’d be,” DiBenedetto said. “It’s a rollercoaster of emotions from the lowest of lows right before Bristol to kind of a high, but mixed emotions and still really down from not knowing what my plans were, to this being through the roof of beyond what I could have imagined.”

DiBenedetto, the driver of the No. 21 Wood Brothers Racing Ford, called the Vegas finish “surreal,” especially within the context of DiBenedetto’s rollercoaster of a career.

Following his stint at Go Fas Racing, DiBenedetto’s bet paid off. He got an improved ride in 2019 when it was announced he would join Leavine Family Racing, which partnered with Toyota and received cars from powerhouse Joe Gibbs Racing.

The 2019 season was DiBenedetto’s best year yet. He scored three top-five finishes, seven top-10 finishes, led 152 laps and had an average finish of 18th while driving the No. 95 car.

It looked like everything was coming up aces for DiBenedetto. And then the dealer dealt him a bad hand.

Despite the on-track success, DiBenedetto and the team announced Aug. 15 they would part ways at the end of the season in a move that made room for Toyota and Joe Gibbs Racing prospect Christopher Bell.

Two days later, DiBenedetto put his talents on full display, nearly winning the Bristol night race. He led 93 laps and was passed by eventual winner Denny Hamlin with 12 laps to go. DiBenedetto settled for his career-best finish of second.

“The pain was like being stabbed 100 times in the chest,” DiBenedetto said after the race. “It was killing me. But it’s a sign of things to come. I’m not done yet.”

DiBenedetto was right. He wasn’t done. He had more to wager. And NASCAR had more to wager on him.

As the NASCAR Cup Series made its way back to Las Vegas Motor Speedway a month later, Wood Brothers Racing announced Paul Menard was retiring after the season and that DiBenedetto had signed to drive the iconic No. 21.

“There was so much unknown, and I couldn’t have imagined or dreamed this was a possibility,” DiBenedetto said. “I had no clue this could be a possibility. Not many people did, either. This is such a good team, with so much experience and history, with really good support.”

DiBenedetto sees the Wood Brothers ride as the best opportunity of his NASCAR career. Wood Brothers Racing is NASCAR’s oldest team, dating back to 1950, and the team has a technical alliance this season with Team Penske.

Wood Brothers Racing has fielded cars for some of NASCAR’s greats, including Junior Johnson, Cale Yarborough and David Pearson. Recently, the team won the Daytona 500 with Trevor Bayne in 2011 and scored Cup win No. 99 with Ryan Blaney in 2017.

The team is looking for win No. 100 under DiBenedetto. But California native DiBenedetto doesn’t feel the pressure. He said after the rollercoaster of a career he’s had, it takes a lot to faze him.

“That’s why I’m thankful for the path to get here has been so high pressure every step of the way,” he said. “Not only to have a season to prove myself, but sometimes a day or a lap to prove myself or situations that are crazy if people knew the whole story. You got to be mentally tough and confident in yourself and your team. I don’t really get stressed. I just go do my job to the best of my ability.”

The 2020 season has barely started, but DiBenedetto has enjoyed opportunities he said he’ll “never forget for the rest of my life.” DiBenedetto made history on the Indianapolis Motor Speedway road course in January as he participated in the first-official NASCAR test on the IMS road course, in preparation for the Pennzoil 150 at the Brickyard NASCAR Xfinity Series race Saturday, July 4.

DiBenedetto is not eligible to run the inaugural NASCAR road course race at IMS, but he will take on the historic 2.5-mile oval Sunday, July 5 for the Big Machine Vodka 400 at the Brickyard Powered by Florida Georgia Line.

DiBenedetto has five starts at the Racing Capital of the World, including an eighth-place finish in 2017. Plus, he has the experience of Wood Brothers Racing at Indianapolis. The team is coming off back-to-back top-10 finishes with 2011 Big Machine Vodka 400 winner Menard, who finished ninth in 2018 and 10th in 2019.

DiBenedetto said he will take in most of the NASCAR weekend at Indianapolis as a fan, which starts with the Driven2SaveLives BC39 Powered by NOS Energy Drink on July 1-2 at The Dirt Track at IMS.

“This is a big, cool change for a really neat weekend,” he said. “We're going to have Xfinity cars running on the road course here, then it's Brickyard 400 weekend, and it's the Fourth of July, and you got the fireworks show, Florida Georgia Line concert. It's a weekend I would definitely want to come to as a spectator. They're going to get a lot of show in one weekend.”

NASCAR may have left Sin City, but DiBenedetto has 18 more opportunities to cash in on his 2-year-old bet before he tries at Indianapolis. Based on his start to the 2020 NASCAR Cup Series season, he might hit the jackpot sooner rather than later.

Tickets are on-sale now for the Big Machine Vodka 400 at the Brickyard Powered by Florida Georgia Line event weekend, which includes a revamped Fourth of July weekend schedule, the Driven2SaveLives BC39 Powered by NOS Energy Drink, FGL Fest and the Pennzoil 150 at the Brickyard NASCAR Xfinity Series race.

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