5 Fast Facts: Largest Winning Margins in Derby History

Jan 18, 2018 Alastair Bull/TwinSpires.com

The Kentucky Derby is always full of great horses, so when it’s won by a huge margin, people invariably think the winner must be a great horse.

A quick look at the Derby record book shows that is frequently the case, though a few surprises do come along the way. Here are the horses with the largest winning margins:

=1) Old Rosebud (1914) – 8 lengths: The first of four horses to win the Kentucky Derby by eight lengths, Old Rosebud is one of the most remarkable and arguably most underappreciated horses in U.S. Thoroughbred racing history. The Derby, won in track record time, was his 11th consecutive victory. An injury in his next start looked to have ended the gelding’s career, but he returned nearly three years later and won 15 of his 21 starts as a 7-year-old, including many of the major handicap prizes. He was still in training as an 11-year-old when he was euthanized after another injury.

=1) Johnstown (1939) – 8 lengths: A winner of seven of his 12 juvenile starts, Johnstown arrived at Churchill Downs a heavy favorite after winning the Wood Memorial. He didn’t get out of the gate well, but had found the lead by a mile and romped away to his eight-length triumph. Big things were expected in the Preakness, but he didn’t handle the muddy conditions and finished fifth. He returned to win the Belmont and went on to win seven of his nine starts that year.

=1) Whirlaway (1941) – 8 lengths: The quirky Whirlaway headed the Experimental Free Handicap after a strong 2-year-old season, but he didn’t take corners well and in the Saratoga Special he hit the outside rail. He ran wide in both the Blue Grass Stakes and Derby Trial, but a one-eyed blinker put on for Derby day helped and he romped away by eight lengths. He went on to take the Triple Crown and was Horse of the Year in 1941 and 1942.

=1) Assault (1946) – 8 lengths: Texas-bred Assault won two of his nine juvenile starts and despite winning the Wood Memorial he started the Derby an 8-1 chance after failing in the Derby Trial. His eight-length derby victory was something of a shock, but it was the first step toward his securing the Triple Crown. He went on to win five of his seven races as a 4-year-old, but wasn’t the same horse in the following three seasons.

=5) Barbaro (2006) and Mine That Bird (2009) – 6 ½ lengths: The horses that share the fifth-largest winning margin had very different tales to tell. Barbaro started the Derby as second favorite and maintained his unbeaten record in the Run for the Roses with his outstanding victory. Unfortunately he shattered his leg in the Preakness, and despite a brave recovery battle, he developed hoof problems and had to be euthanized.

Mine That Bird was the classic rags-to-riches tale. The $9,000 purchase ran well as a 2-year-old in Canada but failed in the Breeders’ Cup Juvenile and, after switching stables to Chip Woolley, he was driven across the country after finishing fourth in the Sunland Derby. On a wet track, Mine That Bird was lengths behind the field early but was guided along the fence by Calvin Borel and surged away to his big victory at odds of 50-1. He showed that effort was no fluke when finishing second in the Preakness to Rachel Alexandra and third in the Belmont, but didn’t regain the same level of form again.

(Barbaro photo by Reed Palmer/Churchill Downs)