Alexander Smith Cochran, the son of Eva Smith Cochran (whose generosity allowed Philipse Manor Hall to become a museum in the early 20th century), began collecting paintings and furniture in 1912 with the express intent of donating these priceless artifacts to the museum. Most of the portraits are of American presidents; also included are members of the Philipse family, military heroes, and other figures from history. Artists include such distinguished names as Gilbert Stuart, John Trumbull, Thomas Sully, and Eastman Johnson.
Upon Cochran's death in 1929, the entire collection of 69 portraits and 36 pieces of furniture was bequeathed to Philipse Manor Hall.