Kreymborg played chess at a near-professional level; he was recognized as a National Master standard player in his youth. On two occasions he played and lost to José Capablanca, including a defeat in 1910 due to a mix-up in his endgame He drew one game with the U.S. Champion Frank Marshall in the 1911 Masters Tournament, but shortly afterward left the chess world after a stunning defeat by Oscar Chajes, returning to the sport roughly 23 years later. He wrote the article 'Chess Reclaims a Devotee', which is semi-autobiographical and also based on Charles Jaffe; the story is well known in chess circles.