In the late 1930s and 1940s, Woodward made a big splash on the racing scene, sending more horses to the track than any other man during that time period.  Racing horses at most of the major tracks around the country, Woodward's top runners included 1940 Champion Two-Year-Old Filly and 1941 Kentucky Oaks winner Valdina Myth, 1942 Kentucky Derby third place finisher Valdina Orphan, and Rounder.

Rounder, imported from Europe by Woodward, became the only horse to ever outrun 1941 Triple Crown winner and Horse of the Year Whirlaway in wire-to-wire fashion.

Woodward prepared his horses to go to the various tracks at his own Valdina Farms, which straddled Uvalde and Median Counties. He had his own training barns, stables, stud paddock, jockeys and trainers.

Unfortunately, Woodward and his wife, Bessie A. McGarry, were killed as the result of a train/car accident near D'Hanis, Texas in May of 1943.

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