This performance got him a drive with Guglielmo Dei's Scuderia Centro Sud, a privateer Formula One team using the Maserati 250F. His first race was the 1957 Monaco Grand Prix, where he scored an impressive third-place finish, the first podium for an American in an F1 Grand Prix. He followed this with a string of good results, coming eighth in the German Grand Prix, and fourth in both the Pescara and Italian Grands Prix. Despite only competing in half of the races, Gregory ended the 1957 season in sixth place in the championship. Gregory only competed in four Grands Prix in the 1958 season, due to injuries sustained through one of his trademark bailouts when his car was set to crash, this time in a sports car race at Silverstone in England. He did manage a fourth place at the Italian Grand Prix, and a 6th in the last race of the year, this Moroccan Grand Prix. Moving to Cooper-Climax for the 1959 season alongside Jack Brabham and Bruce McLaren, he scored two podium finishes - a third place at the Dutch Grand Prix, and a career-best second at the Portuguese Grand Prix. However, he missed the final two races of the season, again due to injuries sustained jumping from a car moments before it crashed. He finished eighth in the Championship, and with teammate Brabham winning the World Championship, Cooper won their first Constructor's Championship. Gregory scored a pole position and set a course record at the non-Championship race at Aintree, but his contract with Cooper was not renewed for the following year. Gregory's early years of competition were marked by many crashes, often the result of pushing sub-par machinery past its ability. He flipped a thankfully rollbar-equipped Maserati at the Venezuelan Grand Prix in 1957, totalled two sports cars in 1958, and another two in 1959 (a Lister-Jaguar and a Tojeiro-Jaguar). In the latter of these incidents he broke his leg and shoulder, keeping him away from his Formula 1 commitments. In 1960, trying to qualify an outdated Cooper-Maserati at Nürburgring he went off the track and was thrown clear of the car. After this period, however, his driving style matured and he began to develop a reputation as an elegant and careful driver. Gregory continued in Formula One until 1965, but mainly with uncompetitive independent teams. He was unable to reproduce the results he obtained early in