50-Year-Old Helio Castroneves Will Try To Win The Indy 500 For A Record Fifth Time

I’m not too proud to admit that I cried big wet tears when Hélio Castroneves won his fourth Indianapolis 500 in 2021. The then-45-year-old driver was fresh off getting fired by Roger Penske, who had recently purchased the motor speedway and the series that runs there. It was a long shot for Castroneves to even be in the running, but he overcame it all to be one of just four men in history to win a fourth time. This May, he’ll be back at the 500 for another shot at the win, again with Meyer Shank Racing, the team he co-owns. If he does manage to pull it off, he’ll be the only person in history to do it five times. 

Castroneves’ fourth Indy 500 win came a full 20 years after his first. He did the unthinkable and went back-to-back in his first and second trips to the Indianapolis Motor Speedway in 2001 and 2002. If he does manage to win in 2026, it’ll be 25 years removed from his moment kissing the bricks for the first time. 

His four wins at Indy alone would signify an incredible open wheel career, but this guy is still making big moves at 50, and wants to do it again. Hélio ran toward the front in the 2025 running of the Indianapolis 500, setting the fastest lap of the race, and proving he’s still got what it takes in his 25th time at the circuit. This year will be his 26th start at the 500, which is still a long ways off from the all-time starts record held by A.J. Foyt and his 35 attempts at the Borg Warner trophy. To match that record, Hélio would need to keep racing until he’s 60, which seems unlikely, but if anyone could do it, it would be him.

Mr. Castroneves made his mark in open wheel racing when he joined the CART championship in the last 1990s and grabbed a handful of podiums for Paul Bettenhausen and Carl Hogan. For 2000 he joined in with Penske’s then-Philip-Morris-sponsored team and began his winning ways. While CART and Indy were still split in 2001, Penske decided to run the full CART season, but come over for a try at the 500 with Hélio as a 500 rookie. It was the first time a Penske car had been fielded at the track since they failed to qualify in 1995, so it was big news. 

The 2001 race marked a major comeback for Penske with Castroneves leading a 1-2 Penske finish ahead of Gil de Ferran. “I think we redeemed ourselves for the lousy thing we did in 1995 … this is the best day of my life coming back like this,” commented Roger Penske from the pits just moments after his driver took the checkered flag. In a blow to the Indy Racing League, the top six drivers to finish the Indy 500 that year were visiting CART racers, popping in for a single race. 

For 2002 the Marlboro Team Penske decided to run the full IRL season with Castroneves at the wheel. At this point in time there hadn’t been a repeat winner of the Indy 500 since Al Unser, Jr. managed a back-to-back in 1970 and 1971 (it has since happened again with Penske driver Josef Newgarden in 2023 and 2024). It is also considered the most controversial race victory in Indy 500 history, as on the 199th lap of the race Paul Tracy was attempting a pass on Castroneves for the lead when a crash occurred at another point on the track drawing a yellow flag. Race officials deemed that the yellow flag came out before Tracy had completed the pass, and therefore Castroneves was the winner. The victory was disputed in court until it was upheld by verdict on July 2nd of that year. 

In 2009 Castroneves was on trial for tax evasion, and if he’d been convicted and sent to jail, he wouldn’t have gotten a third Indy 500 win, let alone a fourth. He won from pole with a solid two-second gap to Dan Wheldon and Danica Patrick. 

Good luck to the Brazilian aiming for a fifth. I’ll be there in May cheering for him.