Richard Raymond Simon is retired American auto racing driver and racing team owner. Simon drove Indy cars in USAC and CART, and made 17 starts at the Indianapolis 500. At the 1988 Indianapolis 500, Simon set a record as the oldest driver in Indy 500 history, a record that was later broken by A. J. Foyt.

The 72nd Indianapolis 500 was held at the Indianapolis Motor Speedway in Speedway, Indiana, on Sunday May 29, 1988. Team Penske dominated the month, sweeping the top three starting positions with Rick Mears winning the pole position, Danny Sullivan at the center of the front row, and Al Unser, Sr. on the outside. Mears set a new track record, becoming the first driver to break the 220 mph barrier in time trials. On race day, the Penske teammates proceeded to lead 192 of the 200 laps, with Rick Mears taking the checkered flag, his third-career Indy 500 victory. The race represented the milestone 50th victory in Championship car racing for owner Roger Penske and Penske Racing.