Cadillac Hotel

Sunset - the Cadillac

“Sunset – the Cadillac” (2003)

(333/12) 366-394 Eddy Street; Cadillac Hotel. Mid-priced hotel with 170 rooms and ninety-one baths in two-, three- and four-room suites, dining room converted to boxing ring 1924. 4B stories. Brick, terracotta trim, decorative moldings and keystones with flat arches, galvanized iron cornice; two-part vertical composition in an E-plan; Renaissance/Baroque ornamentation; alterations: security gate, remodeled ground level, vestibule. Original owner: Andrew A. Louderback, poultry, game and distilling (Louderback lived in a house on this site until 1906). Architects: Meyer and O’Brien. 1907.

A spacious lobby with a red marble fireplace, a mezzanine-level gallery, and grand stairways to a former dining room together indicate that the Cadillac was designed to attract tourists as well as permanent residents. Owned and operated since 1977 by Leroy and Kathy Looper’s Reality House West, the hotel was the first nonprofit-owned SRO in California and was the model for supportive housing as a means to reduce homelessness in the United States.

Source: San Francisco History Center, S.F. Public Library

Cadillac Hotel, 1907.

In 1924 Billy Newman leased the hotel dining room and converted it to a boxing gymnasium. For sixty years Newman’s Gym was the training ground for hundreds of local boxers and numerous world heavyweight champions, including Sonny Liston, George Foreman, and Gerry Cooney. Nineteen-year-old Cassius Clay (the future Muhammad Ali) was Billy Newman’s guest at the gym for several days in 1960, when he was stranded at the San Francisco Airport on his way home from the Rome Olympics with a gold medal and no cash. Legendary jazz artist Miles Davis would often spar at Newman’s when he was in town for a gig. According to gym director Don Stewart, Davis was a very capable boxer who would say to his sparring partners, “Don’t hit me in the face. I’ve got to play tonight.” The oldest boxing gym in America moved in 1984 from the Cadillac to 136 Leavenworth, where it continued to operate until the passing of Don Stewart in 1995.


Miles Davis at Newman’s Gym, 1971. (Photo by Jim Marshall)

Jerry Garcia lived at the Cadillac in 1961. His appointment with destiny came several years later, when a newly-formed band named the Warlocks (Garcia, Ron “Pigpen” McKernan, Bob Weir, Bill Kreutzmann, and Phil Lesh) dropped acid with Ken Kesey and changed their name to the Grateful Dead.


Postcard, circa 1907.

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