H 148.0 cm x W 123.0 cm x D 16.5 cm
A half-length portrait of John Flanigan seated in a green-upholstered wooden armchair. He is angled slightly to the left, with his head turned slightly towards the viewer. The figure has thick, wavy light brown hair, heavy eyebrows, blue eyes, and mutton-chop sideburns. He is wearing a black topcoat, a black waistcoat with a gold watch chain visible, a white high collared shirt, and a black cravat/bowtie. He has a long gold chain of office with small open links around his neck and extending into his lap. The subject sits with his left forearm resting on the arm of the chair and his hand curled over the end of the chair arm; his right arm extends down so that his hand (not visible) rest in his lap. In the background to the left is a plain pillar; in the background to the right is a red drapery panel. There is an illegible signature in the lower left corner along the figure's sleeve.
The painting is housed in a mid 19th century gilt wood and plaster frame. Alternating large and small cabochons on cabled back edge, plain scotia; scroll corners and centres with gadrooned ornament, and intervening smaller scrolls on ogee top edge; cabled half circles on cove; fluted scotia with foliate centres; stick and vine, plain bead sight edge.
Born in Ballymoney, Ireland, John Flanigan was a successful butcher and a superior swordsman. He rose to the rank of major during his more than 30 years with the 1st Frontenac Dragoon Militia. Although only mayor for two terms, Flanigan’s municipal career spanned 30 years. He was a leading member of the local Orange lodge, an Irish Protestant movement known for its anti-Catholic sentiments. Flanigan’s involvement with the Orange controversy that arose prior to the Prince of Wales’ visit to Kingston in 1860 ultimately resulted in the cancellation of the royal arrival.