In 1867, he became a hotel clerk at Cozzen's Hotel in West Point; and later that year went to Omaha, Nebraska when Cozzen rented the Cozzens House Hotel there. He returned in 1869 to Newburgh, New York, and ran the U.S. Hotel there until 1878; and afterwards ran the Pulaski Hotel in Savannah, Georgia until 1883. Then he went to Chicago, and engaged in the oil business, and also engaged in the lumber business in Ottumwa, Iowa. In 1887, he sold out his business interests and returned to Highland Falls.
In 1910, he was investigated for having received $24,000 from lobbyists to push legislation forward. The money was paid into his account at a stock broker firm in Binghamton.