The connections made another big decision in May 2019, opting to ship Vino Rosso west for a start at Santa Anita Park, where he won the Gold Cup at Santa Anita Stakes and thrived at the 1 1/4-mile distance to put away Southern California-based grade 1 winner Gift Box. The race also provided experience as the Breeders' Cup Classic would be contested on the same track and at the same distance in November.

In his race before the Classic, Vino Rosso was disqualified from an apparent Jockey Club Gold Cup Stakes victory and placed second behind Code of Honor for interference. Vino Rosso joins Maximum Security this year as Eclipse Award winners who were disqualified in high-profile races.

Pletcher was convinced Vino Rosso was thriving as he prepared for a return to Santa Anita. Vino Rosso delivered the biggest effort of his career in the biggest race of his career, drawing off to a 4 1/4-length score.