According to racing historian Walter Vosburgh, "For size, bone, and coarseness, Tom Ochiltree surpassed all contemporaries.
"[1] Purchased by J. F. Chamberlain at the 1873 Woodburn yearling sale for $500, he was later resold to tobacco heir George Lynde Lorillard.
He was named after Colonel Thomas P. Ochiltree, who joined the Texas Rangers at age 14, fought for the Confederacy during the Civil War, became a newspaper editor and served as a United States Congressman.
[1] The colt was originally trained by Hall of Fame conditioner Wyndham Walden, the founder of Bowling Brook Farm in Carroll County, Maryland).
Parole was born one year later, bred by Pierre Lorillard IV, the brother and racing rival of Tom Ochiltree's owner.
[1] At age four, Tom Ochiltree returned to trainer Walden and became one of the top handicap horses on the East Coast.
He beat Parole in both the Grand National and All-Aged Stakes, carrying higher weights every time.
[4] On October 24, 1877, at Baltimore, Maryland's Pimlico a "match" race was run between Parole, Ten Broeck and Tom Ochiltree.
By this time Ten Broeck ("King of the Western Turf") was winning everything in the midwest, while Tom Ochiltree and Parole were exchanging wins on the east coast that were so heated that a backer of Parole attempted to poison Tom Ochiltree, an attempt that sickened his stablemate Leander instead.
On the day of the three-way match, perhaps 20,000 people showed up, filling every place in the stands or sitting in their carriages to watch.
Tom Ochiltree died on December 29, 1897, at the Middleburg, Maryland farm of his owner Wyndham Walden at the age of 25.