Richard Whitney received the commission for this portrait through Vose Galleries of Boston, and painted it at Mr. Harrington's home in Salem over the course of three months. Whitney recalled that the commission was for a three-quarter length portrait, and he was greatly concerned over how to paint the 6 ft. 6 in. Harrington, and thus chose a seated pose. A chair from the Senate was brought to Salem for which Harrington was undoubtedly grateful, since the sittings often lasted as long as six hours each. "He's tough," Whitney remembered, "but he has a sense of humor. So he sat in an authoritative manner, but the cigar added to the casualness he also possessed. He told jokes all the time, so he's painted with a crack of a smile, hinting at the humor beneath. I think he was an easy man to capture…he was just delightful. We talked politics all the time and he was just fascinating."