Until next time. Let’s focus on the two most common what-abouts: James Hylton and Helio Castroneves.

and Helio Castroneves (2001, 2002, 2009) as the only drivers to win the Indy 500 more than once while driving for Penske. “At Team Penske, our greatest asset is our human capital; the knowledge and ...

But Power also has seen aging teammates such as Helio Castroneves, Juan Pablo Montoya, and Simon Pagenaud — all Indy winners — move on from Penske's IndyCar team. Power could be next.

IndyCar champion and Indy 500-winning driver Will Power has signed with an agent for the first time in his career to negotiate a new contract with Roger Penske and Team Penske president Tim Cindric.

In early January, Hélio Castroneves, four-time Indy 500 champion, announced that he would attempt to qualify for the 2025 Daytona 500 on February 16 th in partnership with Trackhouse Racing.

But Power also has seen aging teammates such as Helio Castroneves, Juan Pablo Montoya, and Simon Pagenaud — all Indy winners — move on from Penske’s IndyCar team. Power could be next.