Will Helio Castroneves Make History This May?

Meyer Shank Racing co-owners Jim Meyer (top, right) and Mike Shank, a former driver who had run in three Indy 500s.

Last May at the Indianapolis Motor Speedway, after holding off a driver almost half his age for the final two laps, Helio Castroneves climbed out of the cockpit and revived his signature Spider-Man ascent up the fence along the front straightaway.  He pumped his gloved fist to his pit crew and to the fans shouting his name. He climbed down and curled up on top of the wall for a brief moment to let the gravity of the achievement wash over him. Then, after embracing his new boss and team, Helio unsnapped his neck harness and removed his helmet to unleash his omnipresent smile.

That smile is the Brazilian’s defining characteristic. And to be fair, it’s a hell of a smile, much more than a pair of upturned lips. Rather it’s an expression in the fullest sense that involves the entire face. It’s a kid’s grin, honest and effortless, framed by midlife character lines, crow’s feet streaking across his temples like fireworks. From competitive go-karting at the age of 10 on the tracks of South America to achieving the highest measure of success on the world’s most famous oval at 46, Helio has never hidden his passion for racing.

But on this day, there was something else in that smile. Something behind those straight-but-not-too-straight rows of white-but-not-too-white teeth that went beyond mere passion or joy. As Helio accepted the Borg-Warner Trophy, the sterling silver cup that carries the sculpted faces of everyone who has ever won the 500, including three younger miniature happy Helios, he beamed with hard-won gratification, as if he had answered the question of whether Helio had anything left in the tank with a question of his own: How do you like me now?

Helio directed the smile at everyone and no one in particular. He meant it for Team Penske, which had cut him loose after more than two decades and given his seat to someone younger. He aimed it at every other driver, new and old, and anyone else in the paddock who thought his career, or at least the fruitful part of it, had expired. He intended it for everyone in the stands, in the press box, and watching at home who thought that he was too old or that he couldn’t do it without that Penske ride—and even for those miniscule parts of himself that wondered, if only for a second, if they might be right. “This one was important to me,” says Helio, looking back, “because I did it on my own.”

Of course, it takes more than one person to win a race—especially this race. Helio knows that and praises his new team at Meyer Shank Racing. But the dirty little secret of open-wheel racing is that it also takes more than talent, a good crew, and a fast car.

The “500” stands for 500 miles, about twice as long as any other IndyCar race, which means more pit stops for fuel and tires. It also means more time on the track with 32 other cars, a third more than a typical IndyCar field, all vying for position on a narrow track. This adds up to more opportunity for a mistake—yours, your crew’s, or another driver’s—to come between you and that trophy. “A million different things have to fall into place,” says Mario Andretti, one of the all-time great racecar drivers in any series, who only won once at IMS in 29 attempts. “Everybody prepares and puts their best foot forward, but any mistake can mean the race, no matter how good you are on the track. Your car has to perform, you have to rely on your team, and you have to hope that nothing unforeseen is going to happen to you.”

Some of what Andretti is describing is luck—and luck plays a part. But Andretti also says that it’s often up to the driver to be able to account for and adapt to these unforeseen factors as they happen. Yes, with skill, quick reflexes, and instinct. But also purpose. That’s a big part of the reason that Helio is in a position to do what no other racer has ever done this May and win a fifth Indianapolis 500. In the car and out, a good driver drives. But a great driver is driven.

Helio celebrates after his first 500 win in 2001 by climbing the fence.Photo by Dave Parker/AP Photo

HELIO HAD DOMINATED KARTING circuits throughout Brazil, won a national title at 14, and made the jump to British Formula 3. He even took the prescribed and marketed “Road to Indy” through the developmental Indy Lights Series, where he won three races and finished second in points in 1997, first catching the eye of Team Penske, one of the richest and most successful teams in open-wheel racing. But Helio’s first big-time contract actually belonged to someone else.

Greg Moore was a rising star in racing before he lost control of his car in the middle of Turn 2 of California Speedway during the last race of the 1999 season. He spun 500 feet down the track and into the infield grass at more than 220 mph, flipped 30 feet into the air, and rolled into a bare concrete barrier. He died from his injuries later that day. Moore had been about to sign a three-year contract to race with Team Penske. Under pressure from primary sponsor Marlboro, with most proven drivers already signed, the team quickly pivoted to Helio. Less than a week after Moore’s death, Helio signed Moore’s hand-amended contract with the old names and amounts literally crossed out.

Outside of his own team—and perhaps even by some within—it was widely understood that the new kid wasn’t really welcome. Moore had not only been a driver on the rise, but he was also immensely popular in the paddock and on pit row. Add to that the fact that Helio’s first two years in CART had only produced two podiums, one pole, and nothing better than a 15th-place finish in points, and it’s not hard to see how many of his contemporaries felt that he was unworthy of that hastily reassigned seat. And to add to this pressure, Helio didn’t have a lot of explanations if he didn’t succeed quickly. “He was now on the best team in the paddock,” says Tony Kanaan, Helio’s countryman, fellow Indy Lights and IndyCar driver, and friend since their days karting together as kids. “It was a crucial moment for him—he had no excuses. If he didn’t win, he didn’t have a job.”

By the time Helio made his first trip through the 16th Street tunnel into the infield at IMS as a driver in May 2001, he had compiled four series wins, five poles, and a top-10 points finish in 2000 for Team Penske. But that was in CART. None of those wins was on an oval, let alone a 2.5-mile oval with straightaways like the Brickyard. As a full-time CART driver, he was also a cultural outsider at Indy, where only a trickle of the drivers from the rival series had dared to return since The Split with Indy Racing League in 1996. The vaunted Team Penske hadn’t shown its face since failing to qualify a single car in 1995. Even Helio’s effervescence didn’t win over many skeptics. “You didn’t know how bad the [CART] drivers wanted to be here,” says Curt Cavin, who covered racing for The Indianapolis Star for nearly 30 years before taking his current position in communications and content at IMS. “Helio acted very much like the Helio of today, but people doubted his sincerity early on. You were never really sure if you were getting an act. It was like that for a long time.”

It was hard to question Helio’s authenticity when, after leading the most laps, he crossed the finish line 1.737 seconds ahead of his Penske teammate, Gil de Ferran, for his first 500 title, and wowed the crowd as he scaled the fence, a tradition since his first CART win in Detroit. “Everyone has their own path in life, you just have to understand that and believe in yours,” says Helio. “[Winning that 500] was confirmation that I was meant to be here and to keep pushing.”

Helio had not only won on an oval, but he won on the oval, on racing’s grandest stage. And in case anyone else needed “confirmation” of his place in the Penske No. 3 car, he kept pushing and went out and won the 500 again in 2002.

Helio leads Paul Tracy in 2002 shortly before the final yellow flag came out for his second win.Photo by Darron Cummings /AP Photo

EVEN THOUGH HELIO WAS THE FIFTH to win back-to-back titles, and the only one to do it in his first two tries, there were still plenty of naysayers. It was easy for doubters to shrug off the 2001 win because of the post-split field that was still light on top open-wheel competition. Helio’s 2002 victory was controversial. Paul Tracy had pulled past him for the lead on the penultimate lap, a pass that track judges negated because it coincided with a caution flag. Tracy’s team appealed the ruling, but to no avail. “[Helio] wasn’t given the crown of American motorsports in 2001,” says Cavin. “The field wasn’t very good. There were still a lot of doubters about him in 2002; a lot of people thought Paul Tracy won that race. He wasn’t getting the credit in 2001 and 2002.”

But then Helio missed a three-peat by less than a second behind teammate de Ferran in 2003. Even though he couldn’t get past third in the next five 500s, and he never won a series championship, Helio more than proved himself. After Penske joined IRL/IndyCar full time in 2002, he amassed 14 wins and an astonishing 29 poles. As if to solidify both his permanence and his prominence in the sport, IndyCar had even tapped Helio to be the grinning face of American open-wheel racing on the 2008 season of the hit ABC reality competition Dancing with the Stars, launching him into the mainstream after he won the dance-off.

The widespread media attention might have brought more awareness to racing, but it definitely drew more eyes and headlines to what happened next. In October 2008, a grand jury indicted Helio on one count of conspiracy and six counts of tax evasion for failing to report $5.5 million in earnings between 1999 and 2004. Most of that sum stemmed from licensing money Helio was promised in the very contract he and Penske amended following Moore’s death. Helio maintained that he never saw a cent of that money; the government charged that it didn’t matter because it was parked in an overseas account to which he had access. The driver’s defense team urged that he was unaware of the details of his finances and only wanted to race.

The trial took place in Miami and started in March 2009. Proceedings dragged on into April, causing him to miss the season opener in St. Petersburg. If convicted, Helio faced deportation and up to six years in jail. “He’s sitting in Miami, and he doesn’t know if he’s going to be allowed to stay in the country, doesn’t know if he’s going to prison,” says Cavin. “To say his career was in the balance is an understatement. Everything was in the balance.”

The jury deliberated for a week. On April 17, two days before the second race of the season in Long Beach, the jury returned a verdict. Helio was acquitted on all counts of tax evasion. He was back in the car in Long Beach and finished seventh, and drove to a second-place finish on the oval in Kansas the following week. As he entered the month of May at IMS, the remaining conspiracy charge still hung over his head. He still won Pole Day. “Racing was his escape,” says Kanaan. “It’s something else you can focus on, and you don’t sit at home to dwell on other things. Only the top athletes have that capability of really just keying in. At 240 mph, you can’t be thinking of something else. You could lose your life in the race.”

A week before the race, prosecutors dropped the conspiracy charge. Helio was a free man. The 500 itself was relatively anticlimactic. He led the last 15 laps by nearly eight car lengths over Dan Wheldon and finished nearly two full seconds ahead for his third Borg-Warner. He was only the sixth driver to ever win three 500s. “I didn’t know if I was even going to be racing,” says Helio, looking back. “There were so many things out of my control. Here, I had control. Going into the 2009 race, I was so happy. This was like a rebirth with me and my life.”

Helio became the fourth driver to win four times, joining A.J. Foyt, Al Unser, and Rick Mears.Photo by Michael Conroy/AP Photo

THE SPLIT BETWEEN HELIO AND PENSKE was gradual and yet still seemed sudden. Helio followed his 2009 Indy win by finishing fourth in points that year. Over the next eight seasons, he only finished outside of the top five in the standings once, winning a total of eight races. In 2017, he finished no lower than eighth in the last eight races, pulling to within 22 points of the standings lead headed into the final race, only to finish the season fourth, 44 points from his elusive championship. But after the season, Penske decided to cut back from fielding four full-time IndyCar teams to three. Helio was the odd man out.

Penske himself asked Helio to transition from IndyCar to his new venture in the IMSA WeatherTech Sportscar Championship, a merger between prior North American sportscar series that was only three years old and lacked mainstream name recognition. “I didn’t want to leave IndyCar,” says Helio. “But Roger said, ‘I need you to help me out on this program.’ It was a good way of drawing more attention to that series.” In a way, it’s as if the smile had worked against him.

But over the next three years, Helio threw himself into his new challenge. He says he grew to love the new series and tried to glean lessons from racing a completely different kind of car. In 2020, he won four of the season’s nine races en route to a championship—the first of his career. Meanwhile, Penske continued to send him to Indy each May to try for his fourth Borg-Warner. But in three one-off attempts, he never finished higher than 11th. He says it was difficult to parachute into the ever-evolving IndyCar chassis for one month and keep up. By the running of the COVID-delayed 500 in August of that year, everyone in the paddock and the press box knew that Penske was shutting down its IMSA team at the end of the year. For the first time in more than 20 years—after 20 Indy 500s, including 10 top-10 finishes, seven podiums, four poles, three runner-up showings, and three wins—Helio was on his own.

The parting between Penske and Helio was unceremonious and, from all appearances, completely circumstantial. The driver never uttered a negative word about his longtime employer, nor vice versa (Penske and Helio still co-own dealerships and other businesses together). Still, the way things played out, it was hard not to get the feeling that we were witnessing the sunset of a storied career that had reached its expiration date. He was 45. “I had some friends say, ‘Hey, move on,’” says Helio now. “And I said, ‘No.’ I didn’t let it get in my head. My wife told me, ‘No, you’re not done.’ My gut was telling me, No, you’re not done. I knew I would regret it if I had to pull the plug.”

It was actually Penske who initiated discussions between Helio and Jim Meyer and Mike Shank. Meyer Shank Racing is an Ohio-based team that had been competing in IMSA since 2014. Shank had driven IndyCar back in the late 1990s, and he had fielded cars for several IndyCar events, including three 500s, but 2020 was the first time he had backed a driver, Jack Harvey, for an entire season. Harvey was again signed on for 2021, but Shank wanted to expand to a two-car team for six races, including Indianapolis. “We were panning for gold and saw a glimmer in Helio,” says Shank. “We looked at the last time he did a full season in IndyCar, but also how good he is at [IMS]. That really matters to people in this sport. Plus, he had this chip on his shoulder to prove himself.”

Helio understood that Shank was taking a chance on him, but he was also betting on Shank. The driver knew he wouldn’t have the equipment or resources he had at Penske. “An organization like Penske hires you to do one thing,” says Helio. “You show up with a helmet, and the expectation is to drive as fast as you can. You work with the engineer, but they find the tools. Here, you don’t have this, you don’t have that, so you have to think what’s going to make us go to the next level. It made me think differently, not only as a driver, but also as a person behind the wall. It’s not just ‘fast, fast, fast,’ it’s, ‘What tools do we have to make it go fast?’ It’s more exciting for me in a different way.”

After qualifying fifth, Helio started his 21st Indy 500 on the middle of the second row. After 35 lead changes between 13 different drivers, Helio made the final one, pulling the No. 06 Meyer Shank Honda ahead of Alex Palou with two laps to go.

The 12 years between Helio’s third and fourth Indy wins was the second-longest in history. He joined A.J. Foyt, Al Unser, and Rick Mears as the event’s only four-time winners, and he was the only one to do it with two different teams. At 46, he was the fourth oldest to win. “Tom Brady won a Super Bowl, Phil [Mickelson] won the PGA [Championship] … the old guys still got it,” Helio later told the media that day. “Kicking the young guys’ butts, teaching them a lesson.”

Helio celebrates his fourth win in 2021 by climbing the fence.Photo courtesy Meyer Shank Racing

CAN HE DO IT AGAIN? Last July, Helio signed a deal with Meyer Shank Racing to run all 17 IndyCar races in 2022, his first full season in five years. The contract solidified what literally no one questioned for even a moment: that Helio will be back at Indy this year, trying to make history with his unprecedented fifth win.

The track has his back. You can take this statement in a mystical, metaphorical sense—as we’ve illustrated, the hallowed 2.5-mile oval has always been there for one of its favorite sons to bestow its blessings and offer affirmation at crucial points of doubt in his career. But IMS is backing Helio in a very quantifiable financial sense. You can see him singing “Back Home Again in Indiana” in the Speedway’s promotional videos all over social media. His smile will be featured in this year’s race day program and even on the paper tickets. Part of that, of course, is tradition. But it’s easy to see that the track administration and everyone who competes and works for its signature and increasingly niche series would savor the kind of worldwide media attention that a fifth Helio win would bring.

The fans will certainly be pulling for Helio. He’s still easily the most recognizable face on the starting grid, if not in the entire paddock. Besides, who doesn’t want to witness history? Plus, it’s clear that even after 21 years, he still has a connection with the crowd. They love to see him climb the fence. “He developed a lot of fresh fans last year by showing his emotions,” says Andretti. “He doesn’t hold back with the euphoria, and he wants it so bad that when it happens, he’s over the moon. It’s amazing how fans responded to that.”

When he arrives at the Speedway, we know he’ll be prepared. Unlike last year, Helio knows he has a crew and a team who know they can win. He knows he’ll have the equipment. And once he’s behind the wheel, there’s little doubt he’ll have a chance to put himself in a prime position to succeed. Qualifying might actually be what he’s best at—Helio has 31 career open-wheel wins, but 54 poles, including four here in Indy. “I think that’s more impressive,” says Cavin. “I think the ultimate judge of a driver is how quick you are over one lap.”

Will that be enough? Who’s to say? After all, this is a sport where the separation between winner and loser is sometimes just a tenth of a second. Just ask Helio, who’s finished second three times. The difference might come down to whether he can find something else to push him over the edge as he’s done throughout his career. He’s no longer a rookie, and no one is foolish enough to think he’s too old. What does he have left to prove?