Soon after completing the hotel, Smith ran into financial difficulties and sold the hotel, including all fixtures, furnishings, linen, and all other chattel, for $325,000 to oil and railroad tycoon Henry Flagler. Upon purchasing the hotel, Henry Flagler renamed the Casa Monica the Cordova Hotel. Flagler, a founder, with John D. Rockefeller, of the Standard Oil Company, already owned two hotels in St. Augustine, the Ponce de Leon Hotel (now Flagler College) and the Hotel Alcazar (now City Hall and the Lightner Museum). From 1888 to 1902, the hotel featured parties, balls, fairs and charity events.