He became a protégé of Bill Tilden after being defeated by the latter in a match, and he then teamed up with him to win the United States doubles championship in 1918 at the age of 15.

During their long rivalry, they faced each other 102 times, with Richards holding a career record of 52–50 against Tilden.

Richards retained his amateur status for 10 years because his ambition was to compete in the 1924 Olympics held in Paris, France.

Richards was a semifinalist at the French championships in 1926, where he beat Colin Gregory and Bela Von Kehrling, then lost to Henri Cochet.

While there was no official ATP Tour in the 1920s, Richards was one of the pioneers in creating a version of a "world tennis tour", playing in the equivalent of all four grand slams during his career, additional major tournaments, and exhibition matches in front of emperors, presidents, and other heads of states.

[11] After retiring from tennis, Richards joined the Dunlop Tire and Rubber Company as general manager of the sporting goods division and became vice president.

[6] Richards was banned from competing in the amateur Grand Slams when he joined the professional tennis circuit in 1927.