He was suspended for one year after one race for his involvement in a four-horse accident at the starting gate.

He retired as a jockey at age fifty having won more than 2,500 races, then began a second successful career as a horse trainer.

He remained there until fleeing the German occupation of France during World War II.

When Sports Illustrated invited Winkfield to a reception at the Brown Hotel in Louisville in 1961, he was told he could not enter by the front door.

In 2005, the United States House of Representatives passed a resolution honoring Winkfield.