Down and out in Detroit in 1936, Pollard was hired by horse trainer Tom Smith to ride Charles S. Howard's Seabiscuit. The team's first stakes win came in the 1936 Governor's Handicap. Pollard and Seabiscuit won numerous important races, including the 1937 Brooklyn Handicap at Old Aqueduct Racetrack in New York City, the 1937 Massachusetts Handicap at Suffolk Downs in Boston, and famously lost by a nose at the 1937 Santa Anita Handicap. Pollard and Seabiscuit were considered by most as the best pairing of race horse and jockey in the USA at that time. In 1940, Pollard jockeyed the then 7-year-old Seabiscuit to a win the Santa Anita Handicap at Santa Anita Park in Arcadia, California. It was Seabiscuit's last race. Pollard rode Seabiscuit 30 times with 18 wins - all of them stakes or handicaps.