Built in 1863, by Neafie & Levy Ship and Engine Building Company of Philadelphia, Pennsylvania (hull #344) as the Charles Pearson for the Boston Towboat Company of Boston, Massachusetts.
In 1903, the tug was rebuilt. However in 1918, the tug was acquired by the United States Navy. Through the Pilot's Association of New Orleans, Louisiana. Where she was designated as the SP-1390. Although, later that year she was commissioned USS Underwriter.
In 1920, she was redesignated as the YT-44. However later that year, she was recommissioned as the USS Adirondack.
In 1922, the tug was decommissioned. And, struck from the Naval Register on June 6th, 1922. When she was acquired by an individual named B. Mitchell of New Orleans, Louisiana.
The tug was later acquired by the New Haven Railroad of New Haven, Connecticut. Where she was renamed as the Underwriter.
In 1925, the tug was acquired by McAllister Brothers Towing of New York, New York. Where she retained her name.
In 1928, the tug was acquired by the Tice Towing Line of New York, New York. Where she was converted for use as a Stakeboat. And, retained her name. However in 1929, she was abandoned. The vessel was single screw, rated at 600 horsepower.