Helio Castroneves is embracing a milestone year with trademark charm and optimism.

Just hours before the Sonsio Grand Prix on May 10, four-time Indianapolis 500 winner Castroneves was genuinely surprised by a heartfelt 50th birthday celebration thrown by those closest to him – an unusual moment of unexpected emotion for someone who’s seen almost everything in racing.

True to form, Castroneves smiled through the festivities, graciously thanking each guest with the same enthusiasm that’s made him a fan favorite for decades.

Now, his focus shifts to a historic goal of becoming the first driver to win the Indianapolis 500 five times. If he achieves the feat May 25, it will come in his 25th start in the race – fittingly, on the 25th day of the fifth month in his fifth attempt with Meyer Shank Racing after his first 20 with Team Penske.

Castroneves has made three of his “500” starts on May 25, and he finished runner-up twice (2003, 2014) and fourth in 2008.

Whether by fate or sheer drive, the numbers seem to align in his favor, especially the fact that he’s spent literally half of his life competing in the “500.”

Adding to the momentum, Castroneves delivered a promising performance in last month’s Open Test, clocking the sixth-fastest lap at 223.234 mph—an encouraging leap from his 25th-place showing in 2024. With the speed, experience, and spirit still firmly intact, the 109th Indianapolis 500 presented by Gainbridge (10 a.m. ET, FOX, FOX Deportes, FOX Sports app, INDYCAR Radio Network) may just offer the perfect stage for another Castroneves moment.

“The car was pretty flawless,” Castroneves said.

Castroneves’ Indianapolis 500 legacy is already legendary—but the margins separating him from untouchable greatness are razor-thin. Just over half a second (.5601 of a second) across three near-misses kept him from what could have been a mind-blowing seven Indy 500 victories – an achievement that would’ve redefined the record books and racing lore.

Gil de Ferran stopped Castroneves’ back-to-back reign in 2003 with a win by just .2990 of a second. In 2014, Ryan Hunter-Reay topped him by only .0600 of a second, which still ranks as the second-closest Indy 500 finish ever. Takuma Sato bested him by .2011 of a second in 2017.

At 50, with 24 “500” starts under his belt, Castroneves stands at a unique crossroads. He is on the verge of becoming not just the winningest driver in “500” history, but also one of its oldest.

A win this May would not only break his tie with legends A.J. Foyt, Al Unser and Rick Mears but also rewrite age records. He’d surpass Unser as the oldest Indianapolis 500 winner, who was 47 years, 11 months and 26 days in his 1987 victory. He’s also become the third-oldest driver to win any INDYCAR SERIES race – placing him in the rarest of company with Mario Andretti (53 years, 1 month, 7 days) and Louis Unser (57 years, 5 months, 22 days).

Despite the odds and the passing years, Castroneves is showing no signs of slowing down, proving he still has the pace, and perhaps more importantly, the passion and preparation. He's trained for nearly a year to be sharp for this moment, and he’s all-in.

If there’s ever been a time for destiny to align with determination, this is it.

If he qualified for the field of 33 drivers, Castroneves would trail only Foyt (35 starts), Mario Andretti (29 starts) and Unser (27) for most starts. He strives to break a tie with Foyt, Unser and Rick Mears in the four-win club.

Foyt earned his fourth win in his 20th start and spent 15 more years trying to get a fifth “500” victory. The closest he came was runner-up in 1979. He finished fifth in 1989, sixth in 1984 and 1990.

Unser made five more starts in pursuit of No. 5. He finished third in 1988 and 1992.

Mears tried one more time in 1992 to earn his fifth win but crashed and finished 26th.

“Back to my comfort zone,” Castroneves said. “This is what I've been doing for so many years. It's like just coming back where it belongs.

“This is an amazing opportunity. To be already with this incredible gods of racing, Rick Mears, AJ and Al Unser Sr, I'm honored and blessed to be in this position.

“Now having this opportunity to do something nobody ever did. People are saying records are made to be broken in any sport. Why not?

“I'm sure a lot of fans want to see that. I want to see that. I'm sure those guys here, they want to try to stop that. But that's life.”