structural:reformatting, stylistic:style_transfer
Governor of New York

Shortly after Roosevelt's return, Republican Congressman Lemuel E. Quigg, a lieutenant of New York machine boss Thomas C. Platt, asked Roosevelt to run in the 1898 gubernatorial election. Prospering politically from the Platt machine, Roosevelt's rise to power was marked by the pragmatic decisions of Platt, who disliked Roosevelt. Platt feared Roosevelt would oppose his interests in office and was reluctant to propel Roosevelt to the forefront of national politics, but needed a strong candidate due to the unpopularity of the incumbent Republican governor, Frank S. Black. Roosevelt agreed to become the nominee and to try not to "make war" with the Republican establishment once in office. Roosevelt defeated Black in the Republican caucus, and faced Democrat Augustus Van Wyck, a well-respected judge, in the general election. Roosevelt campaigned on his war record, winning by just 1%.

As governor, Roosevelt learned about economic issues and political techniques that proved valuable in his presidency. He studied the problems of trusts, monopolies, labor relations, and conservation. G. Wallace Chessman argues that Roosevelt's program "rested firmly upon the concept of the square deal by a neutral state". The rules for the Square Deal were "honesty in public affairs, an equitable sharing of privilege and responsibility, and subordination of party and local concerns to the interests of the state at large".

By holding twice-daily press conferences—an innovation—Roosevelt remained connected with his middle-class base. Roosevelt successfully pushed the Ford Franchise-Tax bill, which taxed public franchises granted by the state and controlled by corporations, declaring that "a corporation which derives its powers from the State, should pay to the State a just percentage of its earnings as a return for the privileges it enjoys". He rejected Platt worries that this approached Bryanite Socialism, explaining that without it, New York voters might get angry and adopt public ownership of streetcar lines and other franchises.

Power to make appointments to policy-making positions was a key role for the governor. Platt insisted he be consulted on major appointments; Roosevelt appeared to comply, but then made his own decisions. Historians marvel that Roosevelt managed to appoint so many first-rate people with Platt's approval. He even enlisted Platt's help in securing reform, such as in spring 1899, when Platt pressured state senators to vote for a civil service bill that the secretary of the Civil Service Reform Association called "superior to any civil service statute heretofore secured in America".

Chessman argues that as governor, Roosevelt developed the principles that shaped his presidency, especially insistence upon the public responsibility of large corporations, publicity as a first remedy for trusts, regulation of railroad rates, mediation of the conflict of capital and labor, conservation of natural resources and protection of the poor. Roosevelt sought to position himself against the excesses of large corporations and radical movements.

As chief executive of the most populous state, Roosevelt was widely considered a potential presidential candidate, and supporters such as William Allen White encouraged him to run. Roosevelt had no interest in challenging McKinley for the nomination in 1900 and was denied his preferred post of Secretary of War. As his term progressed, Roosevelt pondered a 1904 run, but was uncertain about whether he should seek re-election as governor in 1900.