It’s difficult to imagine a week like Matt DiBenedetto had in August last year. On a Tuesday he was told he would not return as the driver on the NASCAR Cup Series for Leavine Family Racing.

He was a soon-to-be unemployed race car driver.

Four days later, he had his best finish on the top racing circuit, finishing second at Bristol after leading most of the race. Race winner Denny Hamlin even apologized, saying: “I’m so sorry to Matt DiBenedetto. … I hate it. I know it would mean a lot to that team.”

DiBenedetto was still a soon-to-be unemployed race car driver.

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But a relationship forged years ago, a retirement and a break of a lifetime has changed everything.

Less than month after being told he was no longer wanted, he was named to drive one of the most storied cars in NASCAR history, the Wood Brothers No. 21, a car franchise once driven by Cale Yarborough, David Pearson, Kyle Petty, Dale Jarrett and Bill Elliott, among others.

He makes his first start with his new team on Sunday in the Daytona 500.

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“The best way to describe it was through my wife, Taylor,” DiBenedetto said. “We were getting top 10s and top fives and then I find out that I was out of a ride. Then I almost won the race in Bristol and there was all the heartache involved with that. My wife was pretty much crying every day.

“Fast-forward a couple weeks and Taylor is crying every day for the opposite reason, pure joy. That sort of sums up the roller coaster of emotion this sport can put you through and doors opening when you don’t expect them. It’s an opportunity beyond what I could have dreamed up.”

DiBenedetto, 28, is one of the latest drivers trying to make his mark in a sport born in the South who happens to be from California. He was born in Grass Valley and used to race fellow NASCAR driver Kyle Larson at the dirt track in Chico. They join five-time NASCAR champion Jimmie Johnson, who is retiring after this season, and Kevin Harvick, also a Cup Series champion.

But it was after DiBenedetto left Northern California and moved to the Charlotte, N.C., area to race Legends cars that he found some friends with the Wood family.

“He showed up in 2004 and my son was running Legends at the same time in the same division,” said Len Wood, a second-generation co-owner who helps manage the team. “He was about 75 pounds and not as tall as he is now. My wife was running things because I was out racing. She was in charge of all the trailers and all the food and that’s what attracted Matt.”

Monster Energy NASCAR Cup Series Bluegreen Vacations 500 - Qualifying

Matt DiBenedetto, driver of the No. 95 Dumont Jets Toyota, looks on during qualifying Nov. 9 in Avondale, Ariz.

(Jared C. Tilton / Getty Images)

DiBenedetto and the Wood family stayed in touch. Then 15 years later, Paul Menard announced he was retiring from full-time racing in the No. 21 and suggested that DiBenedetto was the right person for the car.

“It all kind of fit right in. About that time the 95 [car team] told him they were moving on to a different driver. To top it off, he had a career make-or-break run at Bristol. It was the right thing for us to do.”

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Wood Brothers Racing didn’t have to think very long about the move.

“He’s such a down to earth guy,” Wood said. “What you see is what you get. There’s nothing fake about him. He’s done the right things to position himself in this sport. So far, hasn’t done anything wrong.”

If the history of the car isn’t enough, DiBenedetto’s first win on the circuit will be a milestone 100th win for the Wood Brothers.

“I would like to win No. 100 this week in the Daytona 500,” Wood said. “It’s one of the hardest races to win because there is so much pressure that goes with this race. … We’ve been so close so many times. We’ve won five Daytona 500s. We’ve also had four seconds. Nobody remembers who finishes second. I’d like to get 100 this year. I’d like to get 104, but that’s not realistic.”

YE Top Photos 2019

Multiple cars crash during the 2019 Daytona 500. The crash included drivers Austin Dillon (3), Daniel Suarez (41), David Ragan (38), Paul Menard (21), Ryan Newman (6), Aric Almirola (10), Matt DiBenedetto (95) and Ryan Blaney (12).

(Chris O’Meara / Associated Press)

After Daytona, the NASCAR circuit moves to Las Vegas before landing in Fontana, Calif., for the Auto Club 400, the third race of the year.

“[Fontana] means a lot to me because I’ll have some family and stuff drive down to that race,” DiBenedetto said. “What sticks out to me is we only race there once a year. It’s crazy, because of the fan base there. They get so excited for us to come there one time a year. Maybe because I’m from the home state, but the support I get really sticks out.”

DiBenedetto has fans in a lot of places. He finished third in fan voting for the most popular driver behind Chase Elliott and Kyle Busch.

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Busch has won 56 races and Elliott six. After five years and 176 races, DiBenedetto is still looking for his first win.

“That would be a legendary one for sure,” said DiBenedetto on the opportunity to win Wood Brothers’ 100th. “It’s neat to be in that position to have the opportunity to grab that. Hopefully that and many more. That’s the plan.”

The plan starts on Sunday.

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