[81] Despite Roosevelt's support for Harrison's reelection bid in the presidential election of 1892, the eventual winner, Grover Cleveland, reappointed him to the same post.[82] Roosevelt's close friend and biographer, Joseph Bucklin Bishop, described his assault on the spoils system:

The very citadel of spoils politics, the hitherto impregnable fortress that had existed unshaken since it was erected on the foundation laid by Andrew Jackson, was tottering to its fall under the assaults of this audacious and irrepressible young man... Whatever may have been the feelings of the (fellow Republican party) President (Harrison)—and there is little doubt that he had no idea when he appointed Roosevelt that he would prove to be so veritable a bull in a china shop—he refused to remove him and stood by him firmly till the end of his term.[80]
New York City Police Commissioner
In 1894, a group of reform Republicans approached Roosevelt about running for Mayor of New York again; he declined, mostly due to his wife's resistance to being removed from the Washington social set. Soon after he declined, he realized that he had missed an opportunity to reinvigorate a dormant political career. 