The second floor of the first Tremont House became home to Chicago's first billiard hall in 1836, and was the favorite hangout of an itinerant criminal named John Stone, who in 1840 became the city's first executed criminal, having been convicted of the rape and murder of a Mrs. Lucretia Thompson.
In 1862, a heavily-inebriated Cap Hyman, the famous Hairtrigger Block gambler and shotgun-spouse of Gentle Annie Stafford, invaded the lobby of the third Tremont house and used his pistol to hold everyone in the hotel hostage for an hour, until police reinforcements arrived.
The fourth and final Tremont was also the site of a shooting in January 27, 1897, according to the New York Times on that date:
The Times story concludes, "The hotel proprietor will discharge manager Kirkland," which seems awfully unfair, as only one of the bullets hit the guest.
D.B. Chandler of New York, agent for the Colgate Soap Company, was shot in the left hand and kicked and beaten until unconscious in Room 203 of the Tremont House at 4:45 o'clock this morning.
According to Chandler's story, he was assaulted by Edward Kirkland, manager of the house, Smiley Corbett, an ex-deputy coroner, and B. McIperson, a former ticket broker. "Early in the evening," said Mr. Chandler, "I went to the Schiller Cafe, where I remained until after midnight. Kirkland, Corbett, and McIperson were also in the cafe. They insulted me several times, and I requested them to stop. At last, I left the cafe and returned to my room. As I was winding my watch, I heard John Bruno, the night watchman, say: 'Open the door.'. I was about to do this when I heard some other person say: 'Break it in.'
The door was finally broken in, and I ran into the bathroom. Then somebody fired three shots through the door, one bullet striking me in the left hand and the others barely missing me. Then the men burst in the door. They jumped on me and kicked me on the head and body until I fainted.
The site of the original Tremont is now the "Theatre District Self Park," a twelve-story parking garage built in 1987, catering to the nearby Randolph Street theaters.