A friend of Cornelius Vanderbilt, he gradually expanded his railroad connections through investments as well as legal counsel.

He was also active in the management of philanthropic institutions, including 19 years as Chairman of the Executive Committee of the New-York Historical Society.

[4][7] An active Democrat, he joined Tammany Hall in 1852 where, after William M. Tweed's fall, he succeeded August Belmont, Sr. as Grand Sachem in 1870.

[9] He was chairman of the Democratic National Committee that supported John C. Breckinridge for the presidency in 1860 and also from 1872 to 1876,[10] where he managed Horace Greeley's presidential campaign.

[13] At his death, he was worth several million dollars, but having had no children, he left all of his money to his nieces and nephews,[6] except for $200,000 in cash and his home at 9 West 34th Street in New York City to his wife, the aunt of Austen George Fox.