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With every triumph, there is agony. Each and every year, someone gets their heart broken in the Indianapolis 500. Maybe it’s in practice, and a crash causes enough injury to make you miss the race. Two years ago, Stefan Wilson suffered heartbreak. He had already qualified for the race, but an injury on the final Monday practice sidelined him from the race. He hasn’t been back in an Indy car since. Wilson’s heartache, was a lucky break for Graham Rahal. He had been bumped from the race by teammate Jack Harvey just a day earlier. Rahal was hired to drive Wilson’s car in the race.

Many times, it is in qualifying. The aforementioned Rahal was devastated when he was bumped from the 2023 field. That lasting image of him sitting on the sidepod of his car, sobbing while being hugged by his wife and daughter was gut-wrenching.

James Hinchcliffe looked absolutely stunned in 2017, when the gun went off and he was still waiting in line. Of course, it hurt even worse when he and his team learned that they were caught unaware that the gun would go off at 5:50 pm, instead of the traditional 6:00 pm. Would those extra ten minutes have put him in the race? We’ll never know.

Everyone is ecstatic to win the Indianapolis 500. Even if they have won it before, they want to win it again. Each year, you can see the elation on everyone’s face in Victory Lane. Unless a dark horse for the month finishes in the Top-Five, few non-winners are celebrating at the end of those 500 miles each May. Look at Pato O’Ward’s face after finishing second to Josef Newgarden last year. That wasn’t being thankful for finishing second. That was despair and heartbreak for not winning.

When the race is over each year, there are a lot more broken-hearted drivers leaving IMS than there are drivers who are thankful for a top finish. Here are some of the biggest heartbreaks at IMS that I can think of – and not in any particular order. I’m just scratching the surface here. Let me know which ones I left out, and that you think are even bigger heartaches than what I am listing…

Ralph DePalma, 1912: It’s sad that an Indianapolis 500 winner might be more famous for a race he lost, than the one he won. In 1912, DePalma absolutely dominated. He took the lead on the third lap of the race and led the rest of the way, until…

At one point, DePalma had a five-lap, eleven minute lead, but then it all went terribly wrong. On Lap 197, his Mercedes began to sputter. By the next lap, the sputter became a more pronounced misfired. On Lap 199, the engine quit entirely on the backstretch and DePalma coasted through Turn Four. At that point, DePalma and his riding mechanic began to push the car to the finish line. As they had the line in sight, Joe Dawson roared past to take the checkered flag. It was later clarified that even if Dawson had pushed the car across the finish line before Dawson, the win would not have been allowed since the car was not under its own power.

Three years later, DePalma won the 1915 Indianapolis 500. He led only 132 laps, instead of the 196 he led in 1912. Did it make up for the heartbreak three years earlier? Probably, but the photos of DePalma pushing his Mercedes in 1912 are a lot more famous than any winning photos from 1915.

Bill Vukovich, 1952: In only his second Indianapolis 500, Bill Vukovich found himself in the lead quickly. Starting eighth, he led a total of 150 laps and appeared to be headed to victory. But on Lap 191, Vukovich broke a steering linkage and his Fuel Injection Special lazily grazed the outside wall of Turn Two before coming to a stop. As he sat fuming; Troy Ruttman sped by and assumed the lead. Ruttman would lead the remaining handful of laps and won the race – becoming the youngest driver to ever do so. His age at the time of his win was 22 years and 80 days, a record that still stands today.

Skeptics say that Ruttman had been gaining on Vukovich for several laps. They claim Ruttman would have passed him before the checkered flag anyway. The Vukovich defenders claim that Vukovich had purposely slowed down with the win seemingly in hand. We will never know, and it doesn’t really matter because Vukovich ended up against the wall in heartbreak, as Ruttman went on to celebrate in Victory Lane. The next two years would find Vukovich in Victory Lane. Had he not had heartbreak in 1952, he would still be the only driver to win the race three years in a row. In pursuit of his third straight win in 1955, Vukovich was fatally injured in a crash coming out of Turn Two.

Parnelli Jones, 1967: Andy Granatelli showed up in 1967 with a turbine-powered car built in total secrecy. It was an odd looking car with the jet engine on the side of the driver. That driver was Parnelli Jones, the 1963 winner. It was not sleek, but it looked like it was built for power. Surprisingly, the car qualified on the outside of the second row. But on Race Day, it wasn’t messing around. Jones blew past pole-sitter Mario Andretti halfway through Lap One. He never looked back.

Jones led the first 51 laps on his way to leading a total of 171 laps. With a little more than six laps to go and Jones seemingly cruising to victory, a simple bearing in the drive shaft broke and the mighty turbine coasted harmlessly to a stop. Parnelli’s day was done, and so was his driving career at Indianapolis. AJ Foyt came around and assumed the lead and went on to become a three-time winner that day.

Based on so many interviews I heard over the years, I think losing that race the way he did haunted Parnelli Jones until the day he died last June at the age of 90.

Michael Andretti, 1992: Michael Andretti qualified sixth in 1992, and started the race directly behind his famous father. He was one of only four drivers who had the new Ford-Cosworth under their more narrowed cowling – the others being Mario Andretti, Eddie Cheever and Arie Luyendyk.

Michael led the first six laps, and ended up leading 160 that cold day. He had a 28-second lead over second-place when his fuel pump failed on Lap 189. Michael Andretti’s car rolled to a stop at the north-end of the track. Suddenly a race that had been filled with crashes and no drama up front, became very interesting. Scott Goodyear had charged from 33rd to the lead, but he was passed by Al Unser, Jr. just as Michael’s car faltered. They would have an epic battle for the final laps, as Unser, Jr. barely edged out Goodyear at the line, in what is still the closest finish in the history of the Indianapolis 500. Scott Goodyear had heartache written all over his face after the race, as he thought about what might’ve been. But his heartbreak did not compare to Michael’s after dominating the race all day.

Emerson Fittipaldi, 1994: Most of the heartbreak I have described so far, has been not the fault of the driver. Mechanical gremlins snatched away what appeared to be a certain victory. Such was not the case in 1994. This one was purely driver error.

The three Marlboro Team Penske cars had the pushrod Mercedes engine, that was supposedly producing over 1,000 hp. Al Unser. Jr. put his on the pole and Fittipaldi was on the outside of the front-row.

Fittipaldi had won the year prior, and was looking to go back-to-back. He dominated the race, leading 145 laps. Fittipaldi had lapped the field, except for Al Unser, Jr. who was running second. On Lap 185, Fittipaldi inexplicably hit the outside wall coming out of Turn Four. Most agree that had he not been trying to lap his teammate, Fittipaldi could have coasted to his third Indianapolis 500 win. Instead, all he had to show for his efforts was a broken rear-wing, a bent suspension and a bruised ego. Fittipaldi climbed out of the car to a chorus of cheers from fans that were thrilled at his misfortune. Wounds were still fresh from his refusing to drink the milk one year earlier. Plus, many saw this as payback for 1989, when Emmo put Little Al into the wall on his way to a win. Now it was Little Al passing the wrecked car of Fittipaldi as he took the checkered flag fifteen laps later.

Many were happy with what transpired on Lap 185 (possibly including me), but it was sheer heartbreak and disappointment on Fittipaldi’s face, as he knew he was the one that had blown it.

JR Hildebrand, 2011: It was the Centennial for the Indianapolis 500. As the race was winding down, it had developed into a fuel-saving race. One by one, all of the leaders pitted. For the longest time, it looked as if Bertrand Baguette would be putting his face on the Borg-Warner Trophy. Mercifully, he pitted as well.

Rookie JR Hildebrand was running low as well, but his crew determined he had just enough fuel to make it if he was careful. Meanwhile Dan Wheldon had no fuel concerns, and had worked his way to second and was charging fast. Throughout the final lap, it looked as though Wheldon was running out of time. If Hildebrand could make it through the last few corners, he was home-free. And then it happened.

As Hildebrand was navigating through Turn Four, he could see the checkered-flag in hand. But a slowing Charlie Kimball upset Hildebrand’s rhythm through that last turn just enough, that he bobbled and smacked the outside wall. As the crippled car made its way to the finish line, Wheldon blew by him just before the line to take the improbable checkered flag for the second time in six years.

As Wheldon made a victory lap, Hildebrand was helped out of his damaged machine which had coasted all the way to the grass inside Turn One. As he got out, he bent over and put his hands on his knees in frustration. Both drivers were in tears. But for far different reasons.

These are just a handful of the major heartaches that have taken place in the previous 108 Runnings of the Indianapolis 500. There are so many more that came to mind as I typed. Some of those I could have mentioned were Team Penske missing the race in 1995, Eddie Sachs in 1961, Lloyd Ruby in 1969, Gordon Johncock in 1977, Rick Mears in 1982, Little Al in 1989, Scott Goodyear in 1995, Scott Goodyear in 1997, Marco Andretti in 2006 and Takuma Sato in 2012.

I barely even touched anything before 1950. What about Bill Holland in 1947? Wilbur Shaw in 1941? There are so many that I’ve left out, it’s hard to even name them all. One thing is for certain, there is a lot more heartache at 16th & Georgetown than there is elation. Who had the biggest heartbreak, in your opinion?

George Phillips

This entry was posted on May 14, 2025 at 4:04 am and is filed under Indianapolis 500. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.