Harry Woolrich was a notorious gambler from Montana who was also heavily entrenched in the gaming scene at the Monte Carlo Dance Hall and Saloon, a premier entertainment establishment in Dawson City during the height of the Alaska Gold Rush. The Jefferson Valley Zephyr reports on 7 January 1898 that Woolrich and two associates were "arrested in Butte for gambling. They conducted a skin game and beat a miner named Hudnott." Though a search of the Montana State Prison index failed to turn up results for Woolrich, he likely entered the Deer Lodge Prison shortly after this incident.