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 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 (USS Underwriter).
In 1920, she was redesignated as the YT-44 (USS Underwriter). 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.
In 1922, she was acquired by an individual named B. Mitchell of New Orleans, Louisiana. Where she was renamed as Adirondack.
The tug was later acquired by the New York, New Haven and Hartford Railroad Company of New Haven, Connecticut. Where she was renamed as the Underwriter.
In 1925, the tug was acquired by the McAllister Brothers Towing Company 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.
In 1929, she was abandoned. Rebuilt in 1903, the vessel was single screw, rated at 600 horsepower.