The Indianapolis 500 has more than a century of history behind it, but the race this year will offer something no one has ever seen before.

For the first time ever, there will be a driver in this race trying for his third consecutive Indy 500 win, and another driver going for a record-breaking fifth victory. Oddly enough, both have ties to Team Penske.

Josef Newgarden became the sixth driver in history to win back-to-back races when he crossed the yard of bricks last May. The last person to do that was Helio Castroneves, who won in 2001 and 2002. Castroneves joined the four-time winner’s club in 2021 and has since been on the “drive for five.”

Castroneves came up one spot short of his three-peat bid in 2003 when he finished runner-up. The same is true for Al Unser, who finished runner-up in 1972 after winning the previous two times. Ironically enough, the winners of those two races in 1972 and 2003 were both cars owned by Roger Penske.

After preventing the last two attempts for a three-peat, Penske can do it again with Will Power or Scott McLaughlin. The Captain would love to celebrate a 21st victory this month. Newgarden delivering it would be a truly remarkable achievement.

Team Penske hasn’t been great this season, but it has been an especially dreadful start for Newgarden. Outside of his podium finish in the season-opener at St Petersburg, he has finished 13th, 27th, 10th, and 12th, respectively. A third championship will not be on the menu this year as he currently sits 12th in the standings.

Obviously, the only thing that matters now is the Indy 500 and the potential for history. That could allow him to focus more on this race and not have to worry about his positioning in the title chase. Ironically, this is the same position that Castroneves finds himself in as he makes his first and only start of the season.

Castroneves is aiming to make his own history. It took 30 years for Helio to join the likes of AJ Foyt, Unser, and Rick Mears. While he is still full of energy, time is running out for “Spiderman” to start his own club.

Helio will make his 25th career start this month. Only Foyt (35), Mario Andretti (29), and Unser (27) have started more.

There is an added element for Castroneves this time around. The technical alliance with Chip Ganassi Racing essentially makes him pseudo teammates with Scott Dixon and Alex Palou. While this is a big help for the entire season, the Month of May is all that really matters to Castroneves.

Newgarden and Castroneves are both aware of the other’s situation. That won’t change their approach or how they race each other. Both will have fast cars, both already have the experience and drive needed to cross the finish line first.

It wouldn’t be a surprise to see one of them get the job done. Expect them to be near the front as the laps tick away. Imagine a last-lap shootout between these two talented drivers. The “Month of May” is just getting started, but a record-breaking race could be on the horizon.