In the late 1990s, Trump tried to build a multimillion-dollar casino with the Seminole Tribe of Florida, according to CNN. In 1998, he held a fundraiser that raised $50,000 to the Florida Republican Party, which led to Bush's election as governor, in addition to numerous fundraisers in 1997.
Bush held fast on his policy, noting in 1999 that three Florida referendums voted down casinos, whether on Native American property or otherwise.
Trump hired Mallory Horne, a powerful state politician — he was a former president of the state senate, and a former speaker of Florida's house — to lobby for the casinos he wanted. By the end of 1998, after Bush was elected, he had given up.