State Assembly by the Tammany leader of the district in which he lived.
In 1886 he was elected mayor of New York City, his nomination having been forced upon the Democratic Party by the strength of the other nominees, Henry George and Theodore Roosevelt; his administration (1887-1888) was thoroughly efficient and creditable, but he broke with Tammany, was not renominated, ran independently for re-election, and was defeated.
As governor he devoted his energies to the construction of the canal, but the opposition to his administration, led by Martin Van Buren and Tammany Hall, became so formidable by 1822 that he declined to seek a third term.
Shepard, in 1901, he resigned from his position of leadership in Tammany, and retired to a country life in England and Ireland.
Upon a platform which called for radical reforms in the administrative departments, the civil service, and the national finances, Cleveland was nominated for president, despite the opposition of the strong Tammany delegation from his own state.