Career
In 1946, he was the leading jockey in America, finishing ahead of future Hall of Fame inductees Ted Atkinson and Eddie Arcaro. Of Jessop"s four mounts in the Kentucky Derby, his best result was two third-place finishes. Among his other victories, Jessop rode in Vancouver, British Columbia, winning the 1961 British Columbia Oaks with the filly Be Famous.
He was also the regular rider of Triplicate.
Jessop retired from in 1970 and settled in Texas where for a short time he was involved with training horses. He had three sons: Richard, Jeffery, and Job Junior.
He had six grandchildren: Dustin, Jeremy, Jarred, Mallory, Dillon, and Taylor. He died in 2001 in Boerne, in Kendall County, Texas.