Shaw’s 2.16-second margin of victory in the 1937 race was the closest to date in the 500, and it stood as the record for an incredible 45 years. With 20 laps to go, Shaw had a comfortable two-minute lead over Ralph Hepburn. However, he noticed that the oil pressure in his Offenhauser engine was dropping, so he backed off to preserve his equipment. Shaw timed it to perfection, leading into the final lap by 14 seconds before barely edging Hepburn across the line. Making the victory even sweeter, Shaw helped design and build his Shaw-Gilmore Special, making him one of only a handful of drivers to win the Indianapolis 500 as an owner/driver.
Following a second place finish in 1938, Shaw returned to Indianapolis in 1939 in a supercharged Maserati Grand Prix car. Seeking his fourth Indy win, Meyer led a race-high 79 laps, but his car blew a tire on the 182nd lap, allowing Shaw to cruise home to win by 1 minute, 48 seconds in what was the first Indianapolis victory for a foreign car since 1919.
Shaw repeated his 1939 win in more dominant fashion a year later, leading 136 laps to become the first driver to win the Indianapolis 500 in successive years. From 1936-39, Shaw racked up three wins and a second place finish at Indy, and he appeared on his way to a record-setting fourth (and third consecutive) victory in 1941. But after leading 107 consecutive laps, a wire wheel failed on the Maserati, pitching the car into a tail-first accident in Turn 1 in which Shaw suffered significant back injuries.