"Dollar Bill," as he was popularly known, was a local celebrity in Kingston. He emerged at Queen's after the First World War as a waiter and refreshment vendor.
It is unknown where he had lived and worked previously, but there is some evidence that he had been in prison for highway robbery. He became an unofficial cheerleader for the Queen's football team and alumni remember him flamboyantly welcoming teams home at Kingston's train station on horseback, wearing a bright green tunic and a top hat as he led the crowd in cheers.
Allen turned to bootlegging in the 1930s and became famous for running a bootleg bar out of an old seaplane hangar in nearby Barriefield, keeping his supplies of booze safely underwater. The bar was a local landmark and was featured in Robertson Davies' play Fortune, My Foe, in which Dollar Bill was called "Chilly Jim."