Cooley, nicknamed "Sir Richard" due to his aristocratic manner,[1] was listed as standing 5 feet 11 inches (180 cm) and weighing 158 pounds (72 kg).

One of the most successful batters on the team, he had the highest batting average at .342 and led the Cardinals in hits, triples, runs scored and total bases.

However, after 40 games in which he had a .307 batting average,[4] he was moved to the Philadelphia Phillies in exchange for Joe Sullivan, Tuck Turner, and an unknown sum of money.

[12] Cooley remained with the Phillies in 1897, when he tied with Fred Tenney, George Van Haltren, and Gene DeMontreville for the MLB lead in at-bats.

[13] Cooley led his team in runs scored and stolen bases, and finished third, behind Ed Delahanty and Nap Lajoie, in hits.

After recording a team-high in batting average and slugging percentage,[14] Cooley was promoted to the Major League Beaneaters.

Next season, under manager Al Buckenberger, Cooley played in 135 games, more than double the previous year for the Beaneaters.

In his final years, he battled alcoholism, which partially contributed to his death from heat stroke in Dallas on August 9, 1937.