Shanghai Bobby is a dark bay or brown colt bred in Kentucky by Stonehaven Steadings. In September he was sent to the Keeneland sales where he was bought for $105,000 by a representative of Starlight Racing. Jack Wold and Donnie Lucarelli, the owners of Starlight Racing, named the horse after their friend Bob Burton, an airline pilot who often flew to Shanghai. He is trained by the five-time Eclipse Award winner Todd Pletcher and has been ridden in all of his races to date by Rosie Napravnik.
Racing career
2012: two-year-old season
Shanghai Bobby made his first appearance on April 19 when he won a four and half furlong race at Aqueduct Racetrack. Two months later he ran in the Track Barron Stakes at Belmont Park. Starting the 1/2 favorite, he won by a length from Handsome Jack. Shanghai Bobby's next race was the Grade II Hopeful Stakes at Saratoga Race Course on September 3. He took the lead early in the straight and won by three and three-quarter lengths from the favored Fortify. In October, Shanghai Bobby was moved up to Grade I class for the Champagne Stakes over one mile at Belmont. Starting the 33/20 favorite, he took the lead a quarter mile from the finish and drew clear to win by five lengths from Goldencents. After the race Pletcher praised the colt's versatility and tenacity, saying that he had "all the tools". For his final start of the year, Shanghai Bobby raced outside New York Statefor the first time when he was sent to California to contest the Breeders' Cup Juvenile at Santa Anita Park. Starting the 7/4 favorite he raced in second place before taking a clear lead two and a half furlongs from the finish. At the turn into the stretch he appeared to be struggling and was briefly headed, but rallied strongly to win by a head from He's Had Enough. Commenting on the horse's performance, Napravnik, who became only the second woman to ride a Breeders' Cup winner, explained that "Bobby gets lost when he's out there by himself".
2013: three-year-old season
Shanghai Bobby's early targets in 2013 were the Jan. 26 Holy Bull Stakes and the March 30 Florida Derby. On Jan. 26 Shanghai Bobby was the 2/1 favorite for the Holy Bull Stakes. He started quickly and led till the straight when he was overtaken by Itsmyluckyday. He finished the race in second behind Itsmyluckyday by six lengths sustaining the first loss of his career. On March 30, 2013 Shanghai Bobby was the 5/2 favorite for the Besilu Stables Florida Derby at Gulfstream Park. He broke sharp and stalked on the inside until the far turn where he weakened to place 5th behind Orb, Itsmyluckyday, Merit Man, and Narvaez. On March 30, Shanghai Bobby was diagnosed with a pelvic stress fracture. He was sent to a farm in Florida to recover. On September 20, Shanghai Bobby made a comeback in his first start after the injury in the Florida Derby, starting in the Aljamin Stakes at Belmont Park, and winning by a half-length. On September 30, it was announced that Shanghai Bobby had sustained an injury to a suspensory ligament and would be retired from racing. He will reside at Coolmoore Stud's American Breeding Branch, Ashford Stud.