Always Dreaming was a dark bay colt who was bred in Kentucky by Santa Rosa Partners (Gerry Dilger and Mike Ryan).
"[5] In the summer of 2016, Bonomo and Vincent Viola, both long-time racing fans from Brooklyn, decided to join forces, a move that affected the ownership of Always Dreaming.
"[6] In early 2017, the Bonomos and Violas sold a minority interest in Always Dreaming to West Point Thoroughbreds and Siena Farm.
"[8] Always Dreaming made his three-year-old debut on January 25, 2017, at Tampa Bay Downs as the 1:5 favorite in a maiden special weight race.
Pletcher also felt lucky to secure the services of jockey John Velazquez, with whom he had a long-term association, for the ride.
Pletcher chose this race rather than the Fountain of Youth Stakes held on the same day as part of a plan to keep the colt from peaking too early in the Derby prep season.
[1][4] The lightly raced colt then stepped up to face Grade I company in the Florida Derby on April 1 at Gulfstream.
Always Dreaming vied for the early lead with Three Rules and State of Honor, then settled into second place down the backstretch.
He shipped to Churchill Downs to train for the race, but attracted concern by his headstrong behavior in his morning workouts.
[12] After drawing post position five in a full field of 20 horses, Always Dreaming was made the 5:1 second choice on the morning line by track handicapper Mike Battaglia.
Longshot Lookin At Lee made a late run to finish second, but Always Dreaming was never threatened, winning by 2+3⁄4 lengths.
"[17] Always Dreaming came out of the Derby in good condition and made his next start in the 2017 Preakness Stakes on May 20, with hopes of winning the second jewel of the Triple Crown.
[18] In the Preakness, he led from the outset, challenged by Derby rival Classic Empire with Cloud Computing stalking the leading pair.
[19] The connections of Always Dreaming elected to bypass the 2017 Belmont Stakes in June to give the colt time to recover for the remainder of the racing season.
On August 26, he finished ninth in the Travers Stakes after pressing the early pace set by the winner West Coast.
[22] Always Dreaming made two starts in 2018, finishing second in the Gulfstream Park Hardacre Mile and fifth in the Alysheba Stakes at Churchill Downs.