The 1914 Democratic Senate primary in NYC, a display of Tammany Hall's against the then Assistant Secretary of the Navy Franklin Roosevelt saw Roosevelt take an embarasing 55% beating in the city, as well as an even more embarasing 32.5% loss in the state.
Convinced to Run by William G. McAdoo after a string of hawkish actions by Roosevelt, and tension with his immediate superiors, Roosevelt went into the campaign thinking that he would both have President Wilson's support as a test of progressive strength against Tammany, and that the senate would give him a greater say over foreign policy.
Further, when Roosevelt announced, Grand Sachem of Tammany Hall Charles F. Murphy gave no indication that he would ultimately support anyone else—thereby allowing him to rest up in the Month of August in preperation for campaining in September.
However, Murphy ultimately did, announcing in September his support for Ambasador to Germany James W. Gerard, leaving Roosevelt in the wilderness as Wilson maintained neutrality between two of his executive apointees.
What made this primary now more embarasing and difficult for Roosevelt was that Gerard had accepted Murphy's support on the condition he remain in Germany, both leaving Roosevelt campaining against an absent opponent and—because of his station—shielding Gerard from criticism.
All of this combined for the aforementioned embarasing loss for Roosevelt; after which he—receiving a noncomittal reply that Gerard would Repudiate Tammany—professed his support for Gerard in the general.
In the end, however, Gerard lost to Former NY Assembly speaker James W. Wadsworth Jr by 5%, the latter serving as New York's senator until he lost reelection in 1926.