In 1918, Guy Bedwell had two highly regarded two-year-olds in his care. Billy Kelly shared American Champion Two-Year-Old Colt honors with James W. McClelland's colt, Eternal. The second outstanding runner under Bedwell's care was Milkmaid who is regarded as the best 3-year-old filly in American racing in 1919 and who would be voted American Champion Older Female Horse honors in 1920. Going into the 1919 season, owner J. K. L. Ross acquired another three-year-old named Sir Barton from John E. Madden. Winless in six starts at two, Sir Barton had good early speed and as such was entered in the Kentucky Derby to serve as a pace-setting rabbit for stablemate, Billy Kelly and his jockey, Earl Sande. The combined betting entry of Billy Kelly and Sir Barton were made the second choice among bettors in the Derby behind favorite, Eternal. As planned, jockey Johnny Loftus immediately took the lead and set the pace with Sir Barton but shocked everyone when never relinquished it and won easily by five lengths over Billy Kelly. Just four days later, Guy Bedwell entered Sir Barton in the Preakness Stakes at the Pimlico Race Course in Baltimore, Maryland. The colt won the race then went on to capture the Withers Stakes in New York and shortly thereafter completed the first Triple Crown in U.S. history by easily winning the Belmont Stakes while setting a track and American record for the then mile and three-eighths race. In addition to Sir Barton, in 1919 Bedwell also trained and raced the Ross-owned filly Constancy who would earn the American Champion Two-Year-Old Filly title. For 1919, Bedwell won his second consecutive national earnings title. In 1921, Guy Bedwell became part of a dispute involving J. K. L. Ross and the New York Jockey Club over the lifting of the ban on jockey Cal Shilling. Shilling worked for Bedwell as an exercise jockey and also helped with horse conditioning. Bedwell had testified before the Maryland State Racing Commission in support of Shilling's application for a jockey's license and as a result he too became a central figure in the controversy. The April 21, 1921 issue of the New York Times quoted from a letter by August Belmont Jr. to J. K. L. Ross saying "the entries of your stable will not be acceptable to this association if ex-Jockey Carroll Shilling or H. G. Bedwell is in any way connected, directly or indirectly, with the same." The matter resulted in Bedwell's horses racing primarily in Maryland for nearly twenty years before he was allowed to compete again at racetracks in New York State. After winning the American Triple Crown with Sir Barton, Bedwell never trained another triple crown race winner but in Canada he won the 1924 and 1926 editions of the Breeders' Stakes, a race that now forms part of the Canadian Triple Crown series. After J. K. L. Ross encountered financial problems and was forced to liquidate his stables, Bedwell trained for various owners including, late in his career, for Elizabeth Arden's Maine Chance Farm. His son, L. G. Bedwell, also became a trainer. Still active in racing, Guy Bedwell died of a heart attack in 1951 having won more than 2,100 races. In 1971, he was posthumously inducted in the National Museum of Racing and Hall of Fame. Bedwell was one of the trainers in American Thoroughbred horse racinghistorian Edward L. Bowen's 2007 book Masters of the Turf: Ten Trainers Who Dominated Horse Racing's Golden Age.
