TALLAHASSEE, Fla. — Billionaire Jeff Greene is jumping into Florida's crowded Democratic primary for governor less than three months before the election.

While a late entry into the race, Greene has enough money to shake up an election where about half the voters are undecided. He filed his paperwork to run Friday, but didn't immediately make a public announcement about the run.

It's not the first political run for Palm Beach real estate tycoon, who lost a U.S. Senate primary eight years ago despite spending $30 million of his own money.

Greene ran for Senate in 2010 and lost by a landslide to then-U.S. Rep. Kendrick Meek despite far outspending the congressman. His campaign was dogged by distractions, including reports that former boxer and convicted rapist Mike Tyson was the best man, and Hollywood Madam Heidi Fleiss was his house guest for a year. There were also news reports about parties on his yacht, which once made a stop in Cuba while the U.S. had a travel ban to the island.

After he lost, he sued what's now the Tampa Bay Times accusing the newspaper of libel during its coverage of the campaign. The newspaper settled the lawsuit in 2016.

Forbes magazine lists Greene as being worth $3.8 billion, with 3,500 apartments in Los Angeles, 2,500 units in Florida, three buildings in Manhattan and five homes.

Greene didn't immediately return a voicemail seeking comment on his campaign.

Two years ago, Greene opened a private school in Palm Beach serving pre-school through grade 6. It has an enrollment of 85 and is expanding to grades 7 and 8 this year.

Greene won't be the only candidate spending millions of their own money on the race. Former Miami Beach Mayor Philip Levine has already spent about $8 million and Orlando businessman Chris King has spent about $2.3 million on the race.

Other Democrats running are former U.S. Rep. Gwen Graham and Tallahassee Mayor Andrew Gillum.

Republicans running include Agriculture Commissioner Adam Putnam and U.S. Rep. Ron DeSantis.

Republican Gov. Rick Scott can't seek re-election because of term limits. Instead, Scott is challenging Democratic Sen. Bill Nelson.