Simon was born in Seattle, Washington. His mother developed multiple sclerosis and died at a relatively young age; his father later left the family, compelling Simon to take responsibility for raising his younger siblings. He received a skiing scholarship to the University of Utah, where during his collegiate career he twice won the Intermountain Ski Jumping championship and for three consecutive years won the Landes Memorial Ski Jump in Alta, Utah. He began racing super modifieds in 1962, and between 1962 and 1967 won more than 30 races in the western United States, including the 1965 South Lake Valley Racing Association championship.
Simon made his first USAC Championship car appearance at Seattle International Raceway in 1969 but failed to qualify. His first start came in 1970 at Phoenix International Raceway, driving a second-hand Vollstedt chassis. He made his Indianapolis 500 debut that same year, finishing fourteenth. At Ontario Motor Speedway later in 1970, Simon recorded his career-best finish of third place, and he closed the year tenth in the 1970 USAC National Championship.
He remained marginally competitive throughout the 1970s without improving significantly on his early results. In 1979, Simon sided with USAC during its split with CART, and by being one of the few drivers to complete the USAC schedule that season, finished eighth in the championship. He moved to CART in 1980 and continued competing through the 1980s. In 1982, Simon survived a spectacular rollover accident at Riverside that received national attention when footage was broadcast on the television program That's Incredible!.
His best CART season was 1987, when he made eleven starts and recorded two top-tens, including a sixth-place finish at the Indianapolis 500, enough for twentieth in the CART championship. A partial 1988 season, in which he logged a ninth-place finish at Indianapolis, was his last as a driver. Simon set the record as the oldest driver in Indianapolis 500 history at that 1988 race, at 54 years and 251 days old. That record was later broken by A.J. Foyt.
Simon's driving career totaled 183 starts across 19 seasons from 1970 to 1988 — 115 in USAC and 78 in CART — including seventeen Indianapolis 500 appearances. He completed 1,954 laps at Indianapolis without leading any, the second-highest such total in race history at the time.
Simon began fielding his own race team in 1983 and shortly afterward developed a model centered on pay drivers. Dick Simon Racing operated as one of the more competitive organizations offering race seats on a sponsored basis, consistently fielding current-year March and Lola chassis with competitive engine packages. Simon retired from driving in 1988, partly because sponsors preferred younger drivers, noting that backers did not want to "sponsor somebody's hobby."
In 1989, the team fielded two fully funded entries with Scott Brayton and Arie Luyendyk, moving toward the front of the competitive field. Simon is credited with helping launch the IndyCar careers of Arie Luyendyk, Raul Boesel, Lyn St. James, and Stephan Gregoire, among others. In 1992, he entered Lyn St. James in the Indianapolis 500, where she became the second woman to drive in the race. The team's best season result came in 1993, when Boesel finished fifth in points with three runner-up finishes.
Simon's record with rookies at Indianapolis was notable: of the many first-time entrants he fielded over the years, none failed to qualify for the race. He never won a race either as driver or as owner, but as an owner recorded six second-place finishes, with a best result of fourth at the 1993 Indianapolis 500 with Boesel.
At 61 years old, Simon took the wheel of Davy Jones' car for shakedown testing ahead of the 1995 Indianapolis 500 while Jones was attending a NASCAR event in California. Simon sold the team to Andy Evans, who reconstituted it as Team Scandia in 1997. Simon returned to ownership in the Indy Racing League in 1999 but saw little success. The operation was shut down after Stephan Gregoire failed to qualify for the 2001 Indianapolis 500.
Simon was an adventurist whose range of pursuits extended well beyond motorsport. He was an experienced skier, scuba diver, licensed pilot, skydiver, and parachutist, claiming national champion status as a parachute jumper and making more than 1,600 jumps during the 1960s. He left a desk job at an insurance company in 1970 to pursue racing full-time. Simon was once questioned by the FBI under suspicion of being the airplane hijacker known as D.B. Cooper; he provided an alibi by demonstrating he was in upstate New York on the date of the hijacking, discussing sponsorship with the president of General Foods.
Dick Simon's dual identity as a long-running Indy car driver and a team owner who consistently supported drivers others overlooked — particularly women, pay drivers, and rookies — gives him a distinctive place in American open-wheel racing history. His Indianapolis 500 age record and his team's unblemished rookie-qualification record at the Speedway stand as tangible markers of a career built on persistence and resourcefulness across a sport that rarely rewarded sentiment.