The venue was created through a joint venture between the City of San Jose, Public Works Administration and local property owners Mr. and Mrs. T.S. Montgomery, who donated the property. The building was designed by Binder & Curtis, in the Spanish Colonial/California Mission Revival style. The venue's naming rights were given to City National Bank in December 2013, with its original name being restored in May 2019. The "Montgomery Theater" is attached to the east side of the building. Seating 486, it is the primary home of the CMT San Jose. The west wing was a convention hall called "Parkside Hall". It opened on September 22, 1977, as the "San Jose Convention Center". It served as the city's main convention center until a new facility of the same name opened across the street in 1989. The building was demolished in 2009. A $25 million renovation of the venue was begun in 2009. A state-of-the-art sound and video system was installed, the building's floor was refurbished, an exterior lighting system was activated, and the loading dock was upgraded. Key improvements planned included a top-line interior lighting system, seating upgrades to replace the decades-old plastic molded chairs, more restrooms, and a new concessions program.
Many of the most popular entertainers and public figures have appeared at the venue creating memorable historic events since its opening in 1936. Barbra Streisand appeared there during her first concert tour in 1963. Bob Dylan and the Hawks played a famous show there on December 12, 1965 and Allen Ginsberg made a tape of it now held by the Stanford University Libraries. Earlier that year the Rolling Stones played a concert there that was attended by Ken Kesey and his Merry Pranksters who electrified a party afterward reportedly attended by Stones members. Richard Nixon made national headlines during an anti-war demonstration at the San Jose Civic. It has presented major sporting events including boxing matches with champions such as Jack Dempsey and Joe Louis. The Civic hosted the final day of the GENESIS 3Super Smash Bros. tournament in January 2016. It was the venue for the trampoline events of the inaugural World Games I in 1981.