Fans of IndyCar racing, as a whole, are a notoriously backwards-looking group. We like to wax poetic about days gone by, looking at the past as if it was perfectly harmonious, action on the track was always scintillating, and everyone involved with the racing was pulling the series in the same direction. No one out there is any more guilty of this than yours truly!! But perhaps our worst offense is putting drivers from our formative years of fandom on a pedestal, leaps and bounds ahead of the drivers we watch on track today.

This state of mind is not only short-sighted and unfair to today’s current crop of legends, but it also keeps us from recognizing exactly how good we, as fans, have it today.

If all goes as expected in the next couple weeks, the Field of 33 for the 105th Indianapolis 500 should see nine former champions taking the green flag on May 30. Should this happen, this starting grid would be second only to the 1992 Indianapolis 500 with the most former winners to start the race when 10 such former winners qualified (plus three drivers who would go on to win the race in future years).

But much like the time period we were about to enter after 1992, the Indianapolis 500, and the sport of IndyCar racing as a whole, are on the verge of falling off the cliff and seeing a great exodus of current legends.

Following the 1992 IndyCar season, a high number of living legends hung up their helmets within two or three years, either by choice or by lack of owners who were willing to still give them rides. Those drivers included names like Mears, Foyt, Unser, Johncock, Sneva, Rutherford (who failed to qualify in 1992 but didn’t ultimately announce his retirement in 1994). Further departure of legends continued in 1994 when Mario Andretti announced his retirement, and, although we didn’t know it at the time, Emerson Fittipaldi would turn his final laps in competition at IMS.

While the pending Open Wheel Civil War certainly didn’t help matters and took more of the day’s top stars away from the Indianapolis Motor Speedway, most of those drivers who ended up on the CART side of the fence weren’t quite racing super stars as they would eventually become. Michael Andretti and Bobby Rahal already had established and legendary careers, but names like Vasser, Zanardi, Moore, and Tracy hadn’t quite into that “iconic” status yet. The sport, as a whole, suffered greatly from the sudden and mass exodus of so many all-time legends in such a short period of time.

As I look at the expected entry list for this year’s Indianapolis 500, it seems clear to me that the sport is on the precipice of another such mass exodus of names who will be seen in future years as legends of the Indianapolis 500. Of the nine former winners expected to be entered this year, it is not unrealistic to think at least six of them will be without rides as soon as 2023. Let’s look at this crop of former winners.

On the side of drivers who most likely will have rides, Alexander Rossi and Will Power are the closest to what anyone might consider a “lock.” Rossi is now entrenched in the NTT INDYCAR Series and, at only 29 years old, is likely to be so for many years to come. Will Power recently announced a new contract extension that will see him continue with Team Penske through at least 2023. Many people were surprised he was re-signed so early in the year by Team Penske to lock him in for three more seasons. Many are also considering that this will likely be the final contract for the now-40 year old Power.

The next two most likely to continue driving after 2022 would be Scott Dixon and Simon Pagenaud. For Dixon, it stands to reason that he will be able to continue driving for Chip Ganassi Racing for as long as he desires to do so. While many drivers – even legends – are said to have a “peak” to their career, Dixon’s entire career has seemingly been a peak, and there is no indication whatsoever that Dixon isn’t driving just as well in 2021 as he has at any other point in his career. As long as Scott wants to continue driving, you have to expect the #9 seat will be his. The question becomes how long he wants to continue racing. Scott is now 40 years old with three young children at home. Should Scott win another championship in 2021 or 2022 to tie AJ Foyt with seven IndyCar championships, he may be tempted to continue driving to secure a record eighth title. However, Scott knows he has absolutely nothing left to prove and nothing remaining to cement his status as one of the all-time legends of IndyCar racing. Perhaps his only motivation may be to win another Borg-Warner Trophy, a goal for which he is perennially on the short-list of favorites to accomplish, and perhaps to eclipse Al Unser’s all-time Indianapolis 500 laps led mark of 644 laps, a mark Scott currently stands only 81 laps away from. I personally think we’ll see Scott drive through at least 2023, but after that, it will be entirely up to Scott to decide if he wants to keep going. He has most certainly earned that right!

I think Simon Pagenaud is also likely to keep driving beyond 2023. The question will become whether his driving will continue to be in an IndyCar and will that continue to be with Team Penske. My hunch heading into 2021 was that Team Penske would likely only retain Power or Pagenaud, but likely not both. Now that Power’s services have already been secured through 2023, that must be putting enormous pressure on Pagenaud to win either the Indianapolis 500 or the INDYCAR Championship (though Tom Sneva will remind you that even winning a national championship with Penske does not guarantee a ride for the next season). And don’t think Pagenaud isn’t keeping an eye on and noticing the performance of rookie Scott McLaughlin. The New Zealand rookie is in the fourth Penske ride for 2021, and it is well known that Roger Penske isn’t a big fan of running four cars. Though he and Tim Cindric have recently indicated they are open to running the fourth car again in 2022, there are certainly no guarantees.

Should Pagenaud’s time in Roger Penske’s IndyCar program be coming to an end, Pagenaud may have an opportunity to continue driving for Penske in his recently-relaunched sports car program or he may leave the team altogether for other pastures. Pagenaud has a history with the team now known as Arrow McLaren SP, but such homecomings are rarely happy reunions. My best guess is that Pagenaud would most likely land at Ganassi Racing should he continue in IndyCar without a ride at Team Penske. How long the #48 experiment will continue is unknown beyond 2022, and the performance of the Marcus Ericsson #8 entry hasn’t exactly been off the chart. If Chip Ganassi had a chance to secure the services of a champion and proven winner like Pagenaud, I have a strong feeling he would jump at such an opportunity.

On the other side of the coin, four drivers that I see as unlikely to continue in the Indianapolis 500 past 2022 include Helio Castroneves, Juan Pablo Montoya, Tony Kanaan, and Ryan Hunter-Reay. With Castroneves, Montoya, and Kanaan on partial season rides, mostly centered around the Indianapolis 500, some owners may be willing to continue giving them rides periodically, but with each passing season, their likelihoods of winning the race fall further and further. All of them are still immensely talented, but well into their mid-40s (except RHR, who just turned 40 last December), each knows there are more days behind them in their career than in front of them. As more of the rising stars continue to gain valuable experience, the need for owners to bring these popular veterans back to provide leadership and knowledge becomes less of a necessity. These legends certainly deserve to continue racing if they so choose, but I, personally, hope they go out when their time comes with their head held high rather than taking the AJ Foyt/Johnny Rutherford route and holding on for several years too long.

Ryan Hunter-Reay is a bit of a wild card. It is honestly hard to know exactly where Ryan’s skills are over the past couple years due to the almost inexplicably and statistically impossible awful luck that has befallen him week in and week out. At some point, however, it is fair to start asking when does bad luck stop becoming chance and instead start becoming the result of preparation and self-inflicted circumstances. No matter how you slice it, RHR hasn’t won a race since the 2018 season finale and has only two podium finishes since the start of the 2019 season.

Hunter-Reay does continue to provide leadership for his Andretti Autosport team, but with the emergence of Colton Herta as a bona fide contender of today and Rossi a threat to win every weekend, it seems that Ryan’s ride is now strictly a result of Michael Andretti’s personal commitment to Ryan and DHL’s continued investment in him. Should the DHL funding dry up and if Michael is presented a chance to jump at another well-funded driver, it’s hard to believe that RHR’s days aren’t numbered, at least at Andretti Autosport.

That isn’t to say that RHR might not be an attractive option for another owner to hire for a one-off Indianapolis ride, but whether Hunter-Reay is interested in accepting such a ride is unknown right now. My hunch is that when RHR’s time at Andretti is done, he will be fine riding off into the sunset (perhaps literally on a large yacht off the Florida coast). I just have a hard time imagining the 2014 “500” winner will drag out his career with a series of one-off rides with various teams long into the time he struggles to stay relevant.

Which brings us to our final former winner – the defending and two-time winner of the “500” – Takuma Sato. Ahhhh, Takuma. If I had made a Vegas bet back in 2010 that Sato would still be in the IndyCar Series in 2021 and have two likenesses on the Borg-Warner Trophy, I would be watching this month’s race from a very posh suite and lighting my cigars with $100 bills. Nobody – and I mean nobody!! – imagined that Takuma would be driving as strongly today as he is. And, oh by the way, Sato is somehow 44 actual years old though he still maintains the look, physique, and enthusiasm of someone closer to 30.

With two wins and a third-place finish in the last four Indianapolis 500s, it’s hard to imagine there being a hotter driver right now at the Indianapolis Motor Speedway. And with Sato excelling on seemingly every oval on the IndyCar calendar (he also won at Gateway in 2019), I think Sato – with the continued backing of Honda and Panasonic – will have a ride at Indianapolis for as long as he wants one. I sincerely hope that continues to be with Rahal Letterman Lanigan Racing because that team finally seems to have found the recipe for success and is perhaps running as strong now as they ever have while running two entries.

However, if for some reason, Sato loses his ride at RLLR and cannot get back into an Andretti car or perhaps into a Ganassi car, I don’t see him continuing to drive just for the sake of driving. Four years of languishing with a sub-par Foyt team left Sato with a best finish in the “500” of 13th (twice) and season-long finishing positions of 17th, 18th, 14th, and 17th. Sato has done plenty to cement his career status, at least at the Indianapolis Motor Speedway, and doesn’t need to hang around just to keep driving around. If he has a solid ride that he thinks can win, I suspect he’ll jump at the opportunity. If not, he’ll walk away with his head held high and flashing that same infectious smile that has drawn so many to him.

So those are your former winners expected to be entered into this year’s Indianapolis 500. We are living in a great and rare time when we can see as many as nine former winners in the race. However, we need to enjoy their presence while they are here because there is a strong possibility that group might be whittled down to as few as three or four within just the next couple years.