Shanghai Bobby was undefeated and untested in four starts going into the 2012 Grey Goose Breeders' Cup Juvenile. After winning the Hopeful at Saratoga by three lengths and the Champagne at Belmont Park by five, the 2-year-old son of Harlan's Holiday was made the 6-5 favorite at Santa Anita. Trained by Todd Pletcher and ridden by Rosie Napravnik, Shanghai Bobby bumped next to Monument at the start but maintained a smooth stride around the first turn and up the backstretch in second place, before gaining a clear advantage at the top of the stretch. He held that position right to the wire, holding off He's Had Enough in the final yards to prevail by a head. The victory secured the 2-year-old Male Eclipse Award for Shanghai Bobby, owned by Jack Wolf's Starlight Stables and partners Michael Tabor, Mrs. John Magnier and Derrick Smith.