Tony Stewart: Three Cup Titles, 49 Wins, and the Only Driver to Win It All on Both Sides of the Fence

Welcome to the Happy Hour Racing Driver Spotlight - where we pull one driver into the garage, look under the hood at their career, and tell you what makes them tick. This week: Smoke.

The Short Version

Tony Stewart is a three-time NASCAR Cup Series champion, a 49-time race winner, and the only person in history to win both an IndyCar-style open-wheel title and a NASCAR Cup title. He raced 18 full seasons in Cup, built a team that won a championship of its own, and bought a dirt track so he could keep racing on Saturday nights. At 55, he is still strapping into race cars, and he is back in a NASCAR truck at Talladega this month.

The Kid From Columbus, Indiana

Anthony Wayne Stewart was born May 20, 1971, in Columbus, Indiana, about 45 miles down the road from the Indianapolis Motor Speedway. That detail matters, because almost everything Stewart did for the next three decades traces back to Indiana short tracks and the big oval at 16th and Georgetown.

He came up the old way, through USAC midgets and sprint cars, and in 1995 he did something nobody had ever done: he won the USAC National Midget, Sprint, and Silver Crown championships in the same season. People still call it the Triple Crown. Two years later he won the 1997 Indy Racing League championship. Then he did the thing almost nobody tries. He left open-wheel racing at the top and went stock car racing full time.

Signature Moments

Stewart's rookie Cup season in 1999 is still one of the best debut years anybody has ever had. He won three races, finished fourth in points, and took Rookie of the Year. No modern-era rookie has finished higher in the standings.

The titles came in 2002 and 2005 with Joe Gibbs Racing in the orange No. 20. In between and after came the wins that meant the most to him personally: the Brickyard 400 in 2005 and again in 2007, at the track he grew up staring at. He climbed the fence at Indy. That image is on about half the die-cast shelves in Indiana.

Then there is 2011, which is the race fans still argue about. Stewart went into the playoffs winless, then won five of the ten Chase races, including the season finale at Homestead where he started last and drove to the front. He and Carl Edwards finished the year dead even on points. Stewart took the championship on the tiebreaker, five wins to one. It is the closest title finish in the history of the format, and he had to win the final race to get it.

His last Cup victory came at Sonoma in 2016, in his final season, after a back injury had already cost him the first part of the year.

By the Numbers

Here is the Cup Series career laid out in the parts that matter. Every figure below is a NASCAR Cup Series total from 1999 through 2016.

Look at the bars and you see what made Stewart different: he won in his first season, he won in his last season, and he won in fourteen of the eighteen years in between. Very few drivers stay dangerous that long.

Team Owner, Track Owner, Drag Racer

In 2009 Stewart stopped being just a driver. He bought into Haas CNC Racing, renamed it Stewart-Haas Racing, and put himself in the No. 14. The team won 51 races over its run and won the 2014 Cup championship with Kevin Harvick, which made Stewart one of the few people to win titles as both a driver and an owner.

He also bought Eldora Speedway, the famous half-mile dirt track in New Weston, Ohio, in November 2004, and did more than keep the lights on. In 2013 he convinced NASCAR to bring the Truck Series to Eldora for the Mudsummer Classic, the first dirt race for a NASCAR national series since 1970.

And he never stopped driving. He won the 2021 Superstar Racing Experience championship. In 2024 he climbed into a Top Fuel dragster, won NHRA Rookie of the Year at age 53, and in 2025 he won the Top Fuel regular-season championship. He is still running Top Fuel in 2026.

This month he is back in a NASCAR truck. Stewart will drive the No. 25 Kaulig Racing Ram 1500 in the Love's RV Stop 225 at Talladega on October 23, his second Truck start of 2026. The first came at Daytona in February, his first NASCAR national series start since 2016, and it ended early in a crash with a 36th-place finish. Talladega is a do-over he clearly wanted.

Tony Stewart is back in the No. 25 Ram 1500 for Talladega.

— Kaulig Trucks (@Kaulig_Trucks) September 24, 2026

Off the Track

Stewart married NHRA Top Fuel driver Leah Pruett on November 21, 2021. Their son, Dominic James Stewart, was born November 16, 2024, and the story of that day is pure Stewart: he was qualifying at the NHRA Finals in Pomona, flew to Arizona for the birth, and was back in Pomona racing four hours later.

He ran the Tony Stewart Foundation from 2003 until it closed at the end of 2024. Over two decades it gave away more than $7 million to groups serving critically ill and disabled children, at-risk animals, and injured racing drivers.

His career also carries hard chapters. In August 2013 he broke the tibia and fibula in his right leg in a sprint car crash at Southern Iowa Speedway and missed the final 15 races of the season. A year later, in August 2014, a sprint car he was driving at Canandaigua struck and killed fellow driver Kevin Ward Jr. A grand jury declined to bring charges, and a civil suit was later settled. Stewart has said it changed him.

Fun Stats

• He is the only driver ever to win both an IndyCar-style national championship (1997 IRL) and a NASCAR Cup Series championship.
• The 1995 USAC Triple Crown has only been done once. By him.
• 62 total NASCAR national series wins: 49 in Cup, 11 in Xfinity, 2 in Trucks.
• Both of his Truck Series wins came at Richmond, in 2002 and 2003. He has never started a Truck race at Talladega until this month.
• He has 35 Cup starts at Talladega with one win, in 2008, and 14 top-10 finishes.
• He was inducted into the NASCAR Hall of Fame in 2020.

The Bottom Line

Tony Stewart is the best argument NASCAR has that a racer is a racer. He won in midgets, sprint cars, Silver Crown, IndyCars, stock cars, and now a Top Fuel dragster, because he could not stand to sit still on a Saturday night. Three Cup trophies is the headline. The thirty-year habit of climbing into whatever has an engine is the actual story.

Rep the No. 14. A few things in stock right now:

• Tony Stewart Signature 2016 #14 Blend Line Hat
• Chase Briscoe "Tony Stewart You Old Goat" 1:24 Elite Diecast
• Clint Bowyer #14 Rush Truck Centers Fitted Hat
• Kevin Harvick #4 Stewart-Haas Performance Hat
• Chase Briscoe #14 Pit Uniform Adjustable Hat

See it all in the Tony Stewart collection. New driver spotlights drop every Thursday.