Midnight Bourbon

A $525,000 purchase at the Keeneland September sale in 2019, Midnight Bourbon broke his maiden in his second career start by 6 1/2 lengths at Ellis Park on Aug. 22. He followed that performance with two consecutive stakes placings: a second-place finish in the Grade 3 Iroquois Stakes at Churchill Downs on Sep. 5, and a third-place effort in the Grade 1 Champagne Stakes at Belmont Park on Oct. 10.

Midnight Bourbon began his 3-year-old season with a win in the Grade 3 Lecomte Stakes at Fair Grounds on Jan. 16. In his next start, he was third in the Grade 2 Risen Star Stakes at Fair Grounds on Feb. 13.

In his final start prior to the Grade 1 Kentucky Derby Presented by Woodford Reserve, the Grade 2 Twinspires.com Louisiana Derby on Mar. 20, Midnight Bourbon was a game second, behind front-running Hot Rod Charlie.

After a sixth-place finish in the Derby, Midnight Bourbon pressed on to the Grade 1 Preakness Stakes at Pimlico on May 15. As the 3-1 second choice, he pressed the early pace and held on to finish second behind Rombauer. 

Midnight Bourbon's next start came in the Grade 1 TVG.com Haskell Stakes on July 17. He was interfered with in the stretch and unseated his jockey. Unfazed by that race, he came back to finish second in the Grade 1 Runhappy Travers Stakes on Aug. 28, setting the pace and holding on behind Essential Quality. 

Midnight Bourbon earned two more grade 1 placings in 2021, although he did not win another race. He finished second behind Hot Rod Charlie in the Grade 1 Pennsylvania Derby on Sept. 25, then finished third in the Grade 1 Clark Stakes Presented by Norton Healthcare at Churchill on Nov. 26. He started his 4-year-old campaign with a second-place finish in the Grade 3 Louisiana Stakes at Fair Grounds on Jan. 22, 2022, finishing three-quarters of a length behind Mandaloun.