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State Assemblyman

In 1881, Roosevelt won election to the New York State Assembly, representing the 21st district, then centered on the "Silk Stocking District" of New York County's Upper East Side. He served in the 1882, 1883, and 1884 sessions of the legislature. He began making his mark immediately: he blocked a corrupt effort of financier Jay Gould to lower his taxes. Roosevelt exposed the collusion of Gould and Judge Theodore Westbrook and successfully argued for an investigation, aiming for the judge to be impeached. Although the investigation committee rejected the impeachment, Roosevelt had exposed corruption in Albany and assumed a high and positive profile in New York publications.

Roosevelt's anti-corruption efforts helped him win re-election in 1882 by a margin greater than two-to-one, an achievement made more impressive by the victory that Democratic gubernatorial candidate Grover Cleveland won in Roosevelt's district. With Conkling's Stalwart faction of the Republican Party in disarray following the assassination of President James Garfield, Roosevelt won election as party leader in the state assembly. He allied with Governor Cleveland to win passage of a civil service reform bill. Roosevelt won re-election and sought the office of Speaker, but Titus Sheard obtained the position. Roosevelt served as Chairman of the Committee on Affairs of Cities, during which he wrote more bills than any other legislator.