Roger Penske has won almost every prize in racing but one
Roger Penske has conquered IndyCar, NASCAR and global business, yet one crown still eludes the 89-year-old "Captain": an overall win at the 24 Hours of Le Mans. His Porsche Penske Motorsport No. 6 car finished second in 2025, just 14 seconds shy of victory. As Penske showcases IndyCar on Washington's streets this weekend, the world's oldest endurance race remains the last major prize missing from his resume.
Key Takeaways
- Penske's teams have won 20 Indianapolis 500s, a NASCAR Cup championship and hundreds of other races.
- The 24 Hours of Le Mans is the one major prize that has always eluded Roger Penske as an owner.
- Penske's No. 6 Porsche 963 finished second at Le Mans 2025, only 14 seconds behind the winner.
- Penske received the Presidential Medal of Freedom in 2019 and bought the Indianapolis Motor Speedway that same year.
- He stood with President Trump as an executive order brought IndyCar racing to Washington for the Freedom 250.
What is the one racing prize Roger Penske has never won?
Despite building one of motorsport's most successful dynasties, Roger Penske has never won the 24 Hours of Le Mans outright. The Detroit News notes that his teams have captured "nearly every crown imaginable," from 20 Indianapolis 500 victories to Brad Keselowski's 2012 NASCAR Sprint Cup Series championship.
Penske first raced at Le Mans in 1963 alongside Pedro Rodriguez, but a broken oil line ended their run in the ninth hour. Team Penske would not return to Le Mans for more than half a century. In a recent interview at the French circuit, Penske called Le Mans "the Number One challenge, the challenge I haven't been able to achieve."
How close did Penske come to winning Le Mans in 2025?
Penske's latest bid came through Porsche Penske Motorsport's No. 6 Porsche 963, which crossed the finish line second overall at the 2025 24 Hours of Le Mans. The car finished just 14 seconds behind the winner, representing Penske's third attempt with Porsche at the world's oldest endurance race.
The near-miss followed a fourth-place finish the previous year. For a man who retired from driving in 1965 after winning his final five races and later delivered Team Penske's 600th win in 2022, the margin stings—but it also signals progress.
What else defines Roger Penske's racing and business legacy?
Born in Shaker Heights, Ohio, Penske started as an SCCA driver and was named Sports Illustrated's SCCA Driver of the Year in 1961. After his first Indy 500 win as an owner in 1972, he expanded into trucking, automotive retail and Detroit Diesel, cementing his role as a Metro Detroit business leader.
In 2019, Penske Entertainment purchased the Indianapolis Motor Speedway from the Hulman-George family, which had owned it since 1945. That same year, President Donald Trump presented Penske with the Presidential Medal of Freedom—though, as photos from the ceremony noted, he had still not won Le Mans.
Why does the Freedom 250 Grand Prix matter for Penske now?
As IndyCar Series owner, Penske helped bring open-wheel racing to the nation's capital. A Detroit News photo shows Penske beside Trump holding a signed executive order aimed at staging an IndyCar race in Washington—now the Freedom 250 Grand Prix celebrating America's 250th anniversary.
The event puts Penske's empire back in the spotlight at a moment when his Le Mans quest continues. For more on racing figures crossing into mainstream news, see our Celebrity Breaking News coverage.