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For more than a century, the Indianapolis 500 has marked the unofficial start of summer, becoming as much of a Memorial Day Weekend tradition as vacations and cookouts.  Winning professional racing’s biggest race is no easy task, however, and doing so can prove vital in catapulting a career, thanks to the whirlwind of honors and media appearances that follow the checkered flag.  But winning the Indy 500 four times – well, that’s the stuff of Indianapolis Motor Speedway legends.

IndyCar has seen some unbelievably talented drivers win the Indy 500 over the years but only three have won it four times: A.J. Foyt, Al Unser and Rick Mears.  This weekend, Team Penske’s Helio Castroneves will once again attempt to add his name to that list and get immortalized on the Borg-Warner Trophy. Castroneves, 44, burst onto the scene in 2001, winning the Indy 500 in his first attempt.  After the win, the Brazilian native climbed the IMS fence like Spider-Man and thus his signature celebration was born. The following year Castroneves won it again, becoming the first driver to win twice in his first to attempts – and the last driver to win it back-to-back.  He followed it up with another win in 2009, becoming the seventh driver to accomplish the feat three times.

In the last five seasons, Castroneves finished second in the Indy 500 twice (2014 and 2017) but last year Castroneves and IndyCar parted ways, though he did elect to return as a part-time driver to continue competing in the IndyCar Grand Prix and the Indianapolis 500.  In the end, he finished 27th in the Indy 500, after starting in the third row, due to a crash near the pits during Lap 145. This season, he’s returning to his iconic yellow vehicle part-time, a crowd favorite at the track, though two weeks ago he finished a lackluster 21st in the IndyCar Grand Prix.

Castroneves is expected to return to Penske to race in the Indy 500 next year as well, so he’s got at least two more chances at tying the historic benchmark.  He might even have a few more shots after that too, especially since Unser won his fourth Indianapolis 500 in 1987, just days before his 48th birthday – he remains the oldest driver to ever win. The clock is certainly ticking for Castroneves and he’s well aware.

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”I want to win (this year) because winning gives me an opportunity to go for five next year and I know I’m capable of it,” he recently told the Associated Press. ”Racing is still my passion, racing is still my love and hopefully I can break the record.”

This year’s crop of 33 drivers is packed with talent but Castroneves will have a solid starting position in the fourth row at No. 12, after averaging 228.523 mph over the course of four laps during qualifying.  He’ll be alongside Conor Daly and Marco Andretti, who is looking to make his own history 50 years after his grandfather, Mario, won. Simon Pagenaud and Will Power are currently the favorites to win, per Oddsmaker, despite the fact that in the last nine runnings the winner has qualified third or worse.

The 103rd Running of the Indianapolis 500 airs this Sunday, May 26, 11 a.m. EST on NBC and it will mark the first time in 54 years the race won’t air on ABC.