Opened in the late 1920s as the Cleveland Club, the 12-story building was built by Frank Meade in the Tudor architectural style. As a further nod to the Tudor style, the interior of the building is adorned with the Tudor Rose and other medieval embellishments.

Lavish parties and events were thrown in the building's ballrooms, drawing various individuals to the Cleveland Club, including the infamous Al Capone. It is rumored the notorious gangster had a private swimming pool and tunnel to nearby Little Italy installed within the Club. Although it was never confirmed he funded either feature, the (now collapsed) tunnel to Little Italy still exists today in the basement of the building.

The building became the Tudor Arms Hotel in 1939, splitting the floors between hotel rooms, a jazz entertainment venue, and the Cleveland Club.