The 4-story Hotel Olive opened in 1912 at the corner of Washington and Franklin Streets across Franklin from the Tampa Times building. It featured a restaurant that catered to the downtown business crowd. In 1925, a 10-story annex was added, and the old 4- 4-story structure was renovated. A veritable skyscraper at the time, it was to house 275 guests and give the hotel 162 rooms. It opened in 1926. In 1930, the building was renamed the Hotel Thomas Jefferson. The popular Chinese restaurant Mikado Yen, known for its Chop Suey, was replaced by a coffee shop. The building experienced another extensive renovation in 1959. Tampa businessman and developer James W. Walters bought the entire block from Florida Ave to Franklin Street in 1961 to build a 600-seat convention center, but that never came to fruition.

The hotel closed in 1967, and in 1969, plans were made to demolish it. In 1978, GTE Realty announced their intent to construct a $128.5-million, 4-block complex on the site comprised of a 38-story Tampa City Center, 17-story, 540-room Hyatt Regency Hotel, 1600-space Fort Brooke parking garage, and central courtyard with shops called the Galleria. Former governor Bob Graham joined the opening ceremonies of the complex, including the parking garage where the Olive Hotel once stood, in April of 1982.   

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