Whitaker became embroiled in a dispute with chess administrators during the early 1930s. He believed he should have been selected into the American team for the 3rd Chess Olympiad, Hamburg 1930 (instead of Harold Meyer Phillips (0.5/2 at Hamburg) or James Allan Anderson (6/17)), or for the 4th Chess Olympiad, Prague 1931. Based on prior competitive results, and on the weak showings by Phillips and Anderson on an otherwise well-performing American team (6th place) at Hamburg, Whitaker may have had a reasonable case. But it is likely that his criminal past (see below) was also a factor in the decision. He went so far as to directly contact FIDE President Alexander Rueb, suggesting that two American affiliate chess organizations be permitted as members of FIDE, allowing two American teams, while other nations had only one, but his argument was dismissed. This approach by an individual to the FIDE President over a national team selection matter was unlikely to win any friends for Whitaker. While seemingly frivolous, questions over which players were best qualified to play on the team did lead American chess administrators to stage a qualifying tournament among Masters, to select the national team for the 1933 Olympiad. By that time, Whitaker was facing serious criminal charges (see below); he was never selected to future teams. American teams without Whitaker were able to claim the Olympiad team gold medals for 1931, 1933, 1935 and 1937, along with many individual medals. By 1939, the Western Chess Association and the National Chess Federation had merged into the United States Chess Federation.