Gregory began racing in November 1952 with a Mercury-powered Allard at a 50-mile SCCA race in Caddo Mills, Texas, retiring with head gasket failure. He then installed a Chrysler hemi-powered engine and raced at Sebring in 1953, again retiring — this time with rear suspension failure. His first win came in his third race, in Stillwater, Oklahoma. Switching to a Jaguar, he won several American races including the Guardsmans Trophy in Golden Gate Park, San Francisco, and a race at Offutt Air Force Base in Omaha, Nebraska. At the end of 1953 he was invited to the 1954 1000 km Buenos Aires in Argentina, finishing 14th with water pump problems.
Throughout 1954 and 1955 Gregory competed in European races driving Ferraris, including the Tourist Trophy at Dundrod and the 24 Hours of Le Mans. He also won the inaugural Nassau Trophy at the Bahamas Speed Week in 1954. Returning to America in 1956, he won several SCCA races.
In 1957 Gregory won the Argentine 1000 km, which earned him a drive with Guglielmo Dei's Scuderia Centro Sud, a privateer Formula One team using the Maserati 250F. At the 1957 Monaco Grand Prix he scored third place — the first podium for an American in an F1 Grand Prix. He followed with eighth in the German Grand Prix and fourth in both the Pescara and Italian Grands Prix. Despite racing in only half the rounds, he finished sixth in the 1957 championship.
In 1958 Gregory competed in only four Grands Prix, hampered by injuries from one of his trademark pre-crash bailouts sustained in a sports car race at Silverstone. He managed a fourth at the Italian Grand Prix and sixth in the Moroccan Grand Prix.
Moving to Cooper-Climax for 1959 alongside Jack Brabham and Bruce McLaren, Gregory scored two podiums: third at the Dutch Grand Prix and a career-best second at the Portuguese Grand Prix. He missed the season's final two races after again injuring himself jumping clear of a crashing car. He finished eighth in the championship; Brabham won the World Championship and Cooper secured their first Constructors' Championship. Gregory set a course record and took pole at a non-Championship race at Aintree, but his contract was not renewed.
Gregory's early career was marked by numerous crashes — he flipped a Maserati at the Venezuelan Grand Prix in 1957, totalled two sports cars in 1958, and in 1959 damaged a Lister-Jaguar and a Tojeiro-Jaguar, breaking his leg and shoulder in the latter. In 1960 while attempting to qualify an outdated Cooper-Maserati at Nürburgring he left the track and was thrown clear. After this period his style matured and he developed a reputation as an elegant and careful driver.
Gregory continued in Formula One until 1965 with uncompetitive independent teams. His best result from this period was sixth at the 1962 United States Grand Prix at Watkins Glen with the UDT Laystall team in a Lotus 24. He retired from the 1962 French Grand Prix while running fourth behind eventual winner Dan Gurney, likely losing his best chance at a maiden Grand Prix victory, due to ignition failure. He won the non-Championship 1962 Kanonloppet at Karlskoga in Sweden with BRP.
Gregory set the overall fastest lap at the 1960 24 Hours of Le Mans. In 1961 he won the 1000 km Nürburgring alongside Lloyd "Lucky" Casner in a Maserati Tipo 61 for the Camoradi Racing Team, and finished fifth in that year's Le Mans in a Porsche RS61 Spyder. In 1962 he won the Canadian Grand Prix sports car race at Mosport Park in a Lotus 19-Climax. In 1964 he contested Le Mans in a Ford GT40, retiring in the fifth hour with gearbox difficulties.
In 1965 Gregory partnered Jochen Rindt — who would become 1970 Formula One World Champion — in a North American Racing Team Ferrari 250 LM, winning the 24 Hours of Le Mans. That same year Gregory competed in the Indianapolis 500, starting from the back of the grid and working up to fifth before retiring with an engine problem.
Gregory later finished second at the 1966 1000 km Monza alongside John Whitmore. He entered 16 editions of the 24 Hours of Le Mans between 1955 and 1972. Following the death of his close friend Jo Bonnier at the 1972 Le Mans race, Gregory retired from motorsport and moved to Amsterdam, where he worked as a diamond merchant before operating a glassware business.
Gregory died in his sleep of a heart attack on November 8, 1985, at his winter home in Porto Ercole, Italy. He had four children: Masten Jr., Debbie, Scott, and Michael. He was inducted into the Missouri Sports Hall of Fame in 2005, the Kansas City C.A.R.B. (Central Auto Racing Boosters) Hall of Fame in 2007, the Watkins Glen Walk of Fame in 2012, and the Motorsports Hall of Fame of America in 2013. Gregory is one of nineteen drivers to have competed in all three legs of the Triple Crown of Motorsport — the Indianapolis 500, the 24 Hours of Le Mans, and the Monaco Grand Prix — and to have won at least one of those events.
This article is based solely on the supplied corpus. No external sources were consulted; claims that could not be substantiated against the corpus were omitted under the drop-the-claim rule.
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