Constructed by Timothy Regan in 1868–69, the Regan Building was the first brick building on the Carthage Square and the first "skyscraper" in southwest Missouri.  The first floor housed three businesses, the second floor contained offices, and the third floor, known as Regan's Hall, served as a major community gathering place.

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One of the building's earliest tenants was a billiard saloon, a controversial business at the time because many billiard halls also served alcohol which was seen as detrimental to the character of young men in the city.  In response, the city enacted regulations requiring licensing fees and restricting access by minors.

 

Regan's Hall became one of Carthage's premier event venues, hosting lectures, dances, church services, festivals, and political gatherings. Among its notable events was a speech by suffragist Susan B. Anthony, titled "Good Women and Bad Men," delivered on January 4, 1876.

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A fire in 1907 destroyed the building's interior, though the front and side walls were saved and incorporated into the reconstruction.  After ownership changed, major renovations in 1915 included an expansion to Lyon Street and the removal of the third floor.  The structure was renamed the Center Building because of its central location within the block.

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Additional fires in 1936 and 1954 led to further rebuilding efforts.  The 1954 fire destroyed the Tiger Theatre, Murray-Duncan Drug Store, and Jaffe's Shoe Store, while damaging neighboring businesses.  Although the drug and shoe stores were rebuilt, the theater was not.

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Over the years, the building housed a wide variety of businesses and organizations, including the Minerva Candy Company, Murray-Duncan Drugs, the Vera Cochran School of Dancing, the American Red Cross, and numerous professional offices.  The building's original iron corner pillars remain visible today as a reminder of its long and resilient history.