Sir Winston, named in honor of Sir Winston Churchill, held off favored Tacitus in the stretch to win the 2019 Belmont Stakes. | Photo: Courtesy NYRA/Derbe Glass2

Trainer Mark Casse was emulating Hall of Famer D. Wayne Lukas, the last horseman to win the Preakness and Belmont with different horses in the same year. Timber Country and Thunder Gulch did the honors, respectively, in 1995, but few would have expected Sir Winston to be in this position just a couple of months ago.

After capturing the Display S. on Woodbine’s Tapeta surface last December, Sir Winston was given three chances to qualify for the Kentucky Derby (Grade 1) without success. He rallied for fourth behind Tax in the Feb. 2 Withers (Grade 3), and again improved position belatedly when fifth in the March 9 Tampa Bay Derby (Grade 2) to Tacitus, the Belmont favorite. A troubled seventh in the April 6 Blue Grass (Grade 2) ended his Derby chances.

Casse regrouped by sending Sir Winston to the May 11 Peter Pan (Grade 3), the local stepping stone to the Belmont. He took a leap forward with a furiously closing second in his best effort so far on dirt. The following week, stable star War of Will captured the Preakness, rebounding from being badly hampered by the disqualified Maximum Security in the Derby