Fifty years ago at Belmont Park, the legendary filly Ruffian, often regarded as one of the greatest female racehorses in American history, faced off in a highly anticipated match race against the top 3-year-old colt Foolish Pleasure. Undefeated and dominant throughout her career, Ruffian had set or equaled stakes records in all nine of her victories, showcasing remarkable speed and versatility from sprint distances to 1 1/2 miles. Owned by Stuart and Barbara Janney and trained by Frank Whiteley Jr., Ruffian was a national superstar whose talent transcended horse racing, much like Secretariat before her.

The match race, intended to pit Ruffian against the best male horses of the Triple Crown season, ultimately became a one-on-one battle with Foolish Pleasure after other contenders declined. Despite being the favorite and ridden by jockey Jacinto Vasquez, Ruffian tragically broke down during the race, leading to her untimely death after surgery. Her loss was deeply felt by fans and the racing community, cementing her legacy as an icon and hero whose greatness continues to inspire new generations.