Derek Schultz: Indy 500 lore is filled with great drivers who came agonizingly close but never won

When he dejectedly rolled the No. 5 car into pit lane at the conclusion of last year’s Indianapolis 500, it didn’t appear that Pato O’Ward was ever going to exit his vehicle.

The 2024 Indianapolis 500 runner-up half raised out of the cockpit, hunched over his steering wheel and remained there for what felt like several minutes while being consoled by his Arrow McLaren team. On the verge of tears, O’Ward gave an emotional post-race interview live on NBC with pit reporter Dave Burns. When describing the feeling of once again falling just short of winning the world’s greatest race at the famed oval, the conversation was punctuated by O’Ward’s agonizing expletive.

“[This place] owes me nothing, but it’s always a heartbreak whenever you’re just so close, especially when it’s not the first time and you just don’t know how many opportunities you have,” O’Ward said, “So close again. So f—ing close.”

As the white flag waved, Pato led the beginning of the 500’s final lap, but an outside charge from Josef Newgarden entering Turn 3 was the knockout blow, eventually giving the defending champion his repeat crown. All that stood between O’Ward and racing immortality was two left turns. But just as it was with his bridesmaid showing in 2022, the 26-year-old helplessly watched another driver pump his fist across the famed yard of bricks.

There have been a bevy of close calls for O’Ward in his short racing career at Indianapolis. Over his five lifetime starts in the Indy 500, he has finished sixth or better four times. He crossed the finish line nine, eight, five and six spots better than he began in those starts, signaling just how fast and competitive he is at an unforgiving place like Indy that often swallows young contestants whole.

Overall, the Mexican driver has accumulated seven wins and 40 top-five finishes in his IndyCar career, including a pair of victories at Mid-Ohio and Milwaukee last year after falling short in Indy. He has become one of the series’ best drivers on the track and most popular personalities off of it.

However, nothing—no victory at other stops on the series calendar or even a season championship—compares to winning in Indianapolis, a fact that all drivers who have turned laps at this place have agreed on.

The old saying is that Indy picks its victor. O’Ward isn’t the only incredible contestant that the iconic racing venue has left waiting on the playground to hear his name called.

Michael Andretti

Retiring with the third-most wins in IndyCar history, the second-generation Andretti led 431 different laps at Indianapolis. But unlike his legendary father, Mario, Michael never led at the checkered flag.

In 1992, Michael had a two-lap lead and was cruising to a breakthrough victory when his fuel pump broke with 10 to go, perhaps the most blatant example of the so-called “Andretti curse.” On three other occasions—1989, 1995 and 2003—Andretti’s car failed him while he was leading the race.

Andretti has a boatload of other accomplishments that make him notable, including a popular video game that bore his name, but his Indianapolis 500 shortcomings fueled by an astonishing amount of bad luck, are a prominent part of his overall racing legacy.

Roberto Guerrero

Like O’Ward, the Colombian driver scored a pair of runner-up finishes at Indy early in his career. But he is perhaps most remembered for his shocking crash during the parade laps of the 1992 race while sitting in pole position.

Guerrero is one of four drivers in history to start the Indianapolis 500 first and finish last, perhaps this race’s most crushing and infamous distinction. After finishing among the top four drivers in his first four Indy starts, Guerrero never recaptured his early success, finishing 20th or worse in nine of his final 11 races, including his ill-fated 1992 entry.

Marco Andretti

Marco never came within shouting distance of Michael’s career successes, but it didn’t take him long to experience his father’s Indy heartbreak. As a 19-year-old rookie in 2006, Marco was passed at the line by Sam Hornish Jr. in what remains the second-closest finish in Indianapolis 500 history at a margin of just 0.0635 seconds.

Andretti finished on the podium three other times (2008, 2010 and 2014) and even sat on pole for the 2020 race (finishing 13th), but he has never come as close as he did as a teenager. In fact, in the 247 IndyCar races he’s driven in since that runner-up finish in 2006, Andretti has won just twice, with only one victory (Iowa in 2011) in his final 14 seasons as a full-time driver in the series.

J.R. Hildebrand and Scott Goodyear

There are other drivers who are most famously recognized for their crushing defeats in Indianapolis. J.R. Hildebrand’s career was unfortunately defined by his infamous last turn crash in the 2011 Indianapolis 500, allowing the late Dan Wheldon to scoot past his skidding National Guard machine to take the checkered flag. Hildebrand never finished higher than 6th in any of his subsequent Indy 500 starts, didn’t podium in any other IndyCar appearance and has largely been a part-time driver ever since.

Scott Goodyear’s most memorable on-track moment may have been being edged by 0.043 seconds by Al Unser Jr. in the 1992 Indianapolis 500. Ultimately a two-time No. 2 finisher at Indy, Goodyear was punted from the lead in the 1995 race due to a late penalty and fell agonizingly short in 1997 after a botched last-lap restart nuked his chance at victory. Goodyear fractured his back after being involved in a massive crash at Indy in 2001, which ended his racing career. He then made a name for himself in the broadcasting booth.

The pre-modern era bridesmaids

Rex Mays, one of the greatest drivers of his era, won four different Indianapolis 500 poles across the 1930s and 1940s, with back-to-back runner-up finishes in 1940 and 1941. He never found Victory Lane, though, as his Indy tries ended at one dozen following a fatal Champ Car accident in California in late 1949.

Ted Horn, who also tragically passed in his 30s in a race car incident, astonishingly finished in the top four nine consecutive times from 1936-48. (Due to World War II, the race was canceled from 1942 to 1945.) Despite never claiming the top spot, Horn still owns the best 10-year run of finishes of any driver in Indianapolis 500 history.

Hall of Famer Dan Gurney was also agonizingly close to Indy fame multiple times, finishing second, second and third from 1968 through 1970, falling short to fellow legends Bobby Unser, Mario Andretti and Al Unser Sr.

Reliving the heartbreak of these star-crossed participants says nothing about Pato O’Ward’s chances to earn his Indianapolis breakthrough at some point. Others were eventually “picked” by the unforgiving oval, like Tony Kanaan, whose decade-plus wait ended with his thrilling victory in 2013, cementing T.K. as one of this generation’s most beloved Indy legends.

Several other arduous and fruitless Indianapolis 500 journeys have been ended in recent years with Will Power (won in his 11th Indy start in 2018) and even Newgarden, who didn’t drink the milk in Victory Lane until his 12th 500 in 2023. The Team Penske teammates’ Indianapolis 500 waits are now a footnote in their tremendous careers—notably for Newgarden, who has become one of only six drivers to go back-to-back in the event’s 108-year history.

A win for O’Ward after dealing with the close calls and the Indy heartbreak would be roundly celebrated by Indy fans, just like it was for Kanaan. Those fans have gravitated toward his talent—but especially toward O’Ward’s reverence of a race they also deeply respect and cherish.

“Two corners short,” a downtrodden O’Ward continued following last year’s race. “I put that car in certain points where I didn’t know if I was going to come out in once piece because I want to win this race so freaking bad.”

Whether he races in two more Indianapolis 500s or 20, there’s no doubt O’Ward will be remembered in the annals of the Indianapolis Motor Speedway. It’s still up to him—and perhaps the unforgiving spirits of the hallowed brickyard—to determine whether those memories will be associated with triumph instead of heartbreak.•

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From Peyton Manning’s peak with the Colts to the Pacers’ most recent roster makeover, Schultz has talked about it all as a sports personality in Indianapolis for more than 15 years. Besides his written work with IBJ, he’s active in podcasting and show hosting. You can follow him on X @Schultz975.