Helio Castroneves’ future in IndyCar is up in the air following an average 2017 season. The three-time Indianapolis 500 winner is rumoured to be on the verge of a series switch (to sports cars) as a favor to Team Penske owner Roger Penske. However Castroneves is Penske’s longest-tenured driver, going back to the team’s CART (Champ Car) days so if anything, team owe him; to let him decide his fate. As such, the 42-year-old Brazilian’s IndyCar future should be for him, and him alone to decide.

Castroneves is a franchise driver, after coming to Penske in 2000. He has been a constant for Penske for 18 years and counting. In that span, he’s amassed 30 total career victories in both Champ Car and the IRL/IndyCar series. All with Penske. He has started on pole in four Indy 500s and taken victory three times. An elusive fourth still awaits.

However in those 18 years, Castroneves has never won an IndyCar championship. He has seen current and former team-mates, and rivals win instead.

If this is indeed his last year in an Indycar, we look back at the four times that Castroneves has been a bridesmaid, but never the bride to the Astor Cup.

Robert Laberge/Getty Images Sport Start slideshow