Today’s question: With the recent announcement of Stefan Wilson with Don Cusick and Dreyer & Reinbold Racing coming together for an Indianapolis 500 presented by Gainbridge entry, the group is starting early and looking to be the small team to make waves in May. There have been plenty of great underdog teams in the NTT INDYCAR SERIES and the Indy 500 over the years, so when looking back the past 25 years, which stands out above the rest to you?

Curt Cavin: It’s probably beneficial that the writer of the question capped it at 25 years as we might be debating this for weeks due to the numerous success stories of the small teams of yesteryear. Twenty-five years takes us back through the 1997 race, but I don’t think you have to go back that far. Two quickly come to my mind, and the first is Juncos Racing and Kyle Kaiser bumping Fernando Alonso from the field in 2019. But while that feat was mighty, it was only in qualifying and not the race, which is infinitely more important. So, I’ll go with Bryan Herta Autosport’s effort in winning the 2011 race with Dan Wheldon. Yes, Wheldon was a proven commodity at Indy, having won the 2005 race and finished in the top four with three different teams five times in eight races before suiting up with Bryan Herta’s group. Today, Herta has an established place in the NTT INDYCAR SERIES field, but 2010 was his first year competing at the Speedway as an entrant, and Sebastian Saavedra made the field with what, in effect, was an Indy NXT operation. At the 2011 season-opening race in St. Petersburg, Herta announced that his team would take a one-off shot at the “500” with Wheldon, who was unemployed, in a partnership with Sam Schmidt Motorsports, which only had one top-10 finish in nine years of competing at Indy. The pairing was widely celebrated, but I remember thinking Wheldon wouldn’t contend as he did the two previous years with Panther Racing – a pair of second-place finishes. The Schmidt cars were fast in qualifying, with all three cars earning starting spots in the first two rows and Alex Tagliani winning the pole, but they weren’t flashy in the race. In fact, Wheldon never took the lead until he passed JR Hildebrand’s damaged car coming to the checkered flag. It’s not the biggest upset in Indy history, but it was a surprise, for sure.

Joey Barnes: When looking at the Indianapolis 500, few things compare than a reigning INDY NXT champion edging out a two-time Formula One World Champion as what Kyle Kaiser did when upsetting Fernando Alonso to make the field of 33 in 2019. However, I’ll go a step further and even note a great underdog story for that particular qualifying weekend and highlight Ben Hanley and DragonSpeed. The squad founded by Elton Julian had built a very stout resume in sports car racing and only made two starts in the NTT INDYCAR SERIES in 2019 (St. Petersburg, Barber Motorsports Park) before venturing into an oval debut at Indianapolis Motor Speedway. Hanley was smooth in the cockpit and delivered four crisp laps to qualify a respectable 27th. The team that many predicted to miss the show ended up making it on the first day and dodged the drama of battling Alonso in the Last Row Shootout. Despite the remarkable effort, though, a mechanical issue ended Hanley & Co.’s race after 54 laps and with a finish of 32nd. When looking at the NTT INDYCAR SERIES as a whole, my mind keeps going back to the 2015 and 2016 seasons for Graham Rahal. At the time, Rahal Letterman Lanigan Racing was a single-car outfit with little resources punching well above its weight and trying to make a return to prominence. In 2015, Rahal took scored his first win of the campaign in an ultra-competitive race at Auto Club Speedway, which marked the team’s first victory since 2008 (Ryan Hunter-Reay, Watkins Glen). Rahal collected another victory along the way and gathered six podiums en route to finishing fourth in the championship standings. He was one of only two drivers not in with Andretti, Ganassi or Penske to finish in the top 13 (Sebastien Bourdais in 10th being the other). Rahal backed it up the following year with one win and four podiums to finish fifth in the title race and was the only driver not with the aforementioned “Big Three” to finish in the top 13 in the overall standings.

Paul Kelly: It’s hard to beat the giant-slaying story by Juncos Racing and Kyle Kaiser, who bumped Formula One World Champion Fernando Alonso from the Indianapolis 500 presented by Gainbridge field in 2019. Super impressive, although McLaren Racing’s “500” effort that spring was far from buttoned up, and it showed. I also think back to my first year working at the Speedway, in 1998, when Greg Ray qualified on the front row for low-budget Knapp Motorsports, a team that in 1997 had a bucket outside of its garage in Gasoline Alley for fan contributions to help fund its Month of May effort. But the underdog story that always sticks with me is Felipe Giaffone earning a spot in the 2005 Indianapolis 500 field on Bump Day for AJ Foyt Racing. Giaffone wasn’t an underdog at that time; he was unemployed. Legendary team owner A.J. Foyt learned Giaffone was in Indy on Bump Day and called the Brazilian driver’s number. Giaffone was shopping in a Babies ‘R Us store in Indianapolis when he answered his cell phone – truth, not urban legend. Foyt told Giaffone to hustle over to the Speedway, and Super Tex would have a car, helmet and driver’s suit waiting for him. Giaffone didn’t even have a credential for the race and flashed his expired 2004 driver season pass to get through the gates. He made his four-lap run and earned the 33rd and last spot in the field, bumping Arie Luyendyk Jr. from the starting grid. Sure, Giaffone was a proven talent at Indy, starting fourth and finishing third just three years earlier. But going from looking at baby strollers to a starting spot in the world’s most prestigious auto race in a matter of four hours on one fateful Sunday afternoon? That’s tough to top.