The Trump Family's Biggest Controversies In Florida

Donald Trump is no stranger to reports of controversy and impropriety. Even before throwing his MAGA hat into the political arena, the Manhattan property magnate was a tabloid fixture and Page Six frequent flyer. Not surprisingly, the scandals increased in scale and volume as his political star rose. And as the Trump family began spending less time in the Big Apple and more in the Sunshine State, contretemps and controversies migrated with them.

The Trumps live large in Wall Street South. Ivanka Trump and Jared Kushner enjoy a life of leisure that mere mortals can only dream about. Eric and Lara Trump's Florida home really puts the P in palatial sprawling mansion. And, not to be outdone, Donald Trump Jr. and Kimberly Guilfoyle kick back in a $9.7 million pad 20 miles down the road from daddy dearest.

Meanwhile, as with many things in Trump World, the truth about Donald and Melania Trump's life at Mar-a-Lago is a little hazy. The official line is that everything is peachy within their "Winter White House." However, now and then, a story surfaces that allows for a peek behind the orange curtain, revealing that something is rotten in the state of Alligator. From the ups and downs of Donald and Ron DeSantis' relationship to swastika boat parades to raids that go bump in the night, we're checking out the Trump family's biggest controversies in Florida.

Nothing screams fun family day out on the water like swastika flags fluttering gently in the afternoon breeze. Or not. Still, that was the scene that Jupiter, Florida, residents were met with during the Donald Trump Boat Parade in October 2024. An onlooker posted pics on X, formerly Twitter, showing three masked (and two face-baring) men bobbing along in a speedboat with swastika and Trump flags attached to either side of the stern. Meanwhile, a video shows the vessel getting water-bombed by the speedboat it's following. Before the drenching, the passengers can be heard chanting, "Sieg Heil! Hail Trump!"

Cool. pic.twitter.com/4T7chITaVA

— Lord Matthew Kobilan (@MatthewKobilan) October 14, 2024

According to comments, swastikas weren't limited to just the Jupiter region of the state. "We got them in Orlando," a different Floridian claimed. One devout MAGA supporter was there for it. "In that case I am moving to Orlando!" they vowed. Meanwhile, a second claimed it was a false flag operation. "If you are wearing a mask you are not MAGA. These are either Feds or antifa masquerading as Trump supporters. If you are dumb enough to fall for this bs then ... " they insisted.

Donald Trump's national press secretary also played the blame game. "Kamala's supporters are reaching all-time lows. Social media posts show that genuine Trump supporters identified these idiots as liberal activists trying to create fake news," Karoline Leavitt told Newsweek. "They clearly responded accordingly."

Donald Trump and Ron DeSantis' relationship has been a rollercoaster ride. Considering the popularity of MAGA in Florida, you'd think the former POTUS and the state governor would be besties. But, not so. In fact, Trump's thrown more insults DeSantis' way than he's had court appearances. Well, maybe not, but still.

In 2018, they were political besties. Trump fangirled over DeSantis and urged Floridians to vote him into the governor's mansion. "Such a fantastic win for Ron DeSantis and the people of the Great State of Florida. Ron will be a fantastic Governor. On to November!" Trump raved after his victory. However, it all went south after DeSantis emerged as a potential 2024 presidential candidate. Let the name-calling begin. "Ron DeSanctimonious," Trump called him in November 2022. In February 2023, the New York Times claimed Trump was toying with a new nickname. He denied the report — kind of — on Truth Social. "I will never call Ron DeSanctimonious' Meatball' Ron, as the Fake News is insisting I will," he wrote, insisting, "it would be totally inappropriate to use the word 'meatball' as a moniker for Ron!"

"I think it's so petty. I think it's so juvenile ... and honestly, I think that his conduct, which he's been doing for years now, I think that's one of the reasons he's not in the White House now," DeSantis said of Trump's name calling and mocking in a June 2023 interview with Jack Heath.

Speculation has been rife regarding the relationship between Donald Trump Jr. and Kimberly Guilfoyle. There hasn't been even a whisper of a wedding date since they got engaged on New Year's Eve 2020, and things have appeared chilly between the two of late. Reports of trouble in paradise have been further fueled by Don Jr.'s alleged affair with Florida socialite Bettina Anderson.

Gossip surged through West Palm Beach after photos of Don Jr. and Anderson getting cozy over an intimate lunch at the Royal Poinciana Plaza's The Honor Bar surfaced online. "She seemed totally smitten with Don — and he with her," an onlooker told the Daily Mail. "They looked totally relaxed; she wearing a white shirt tied off to show her midriff and wide-leg pants, he in shorts and a t-shirt." The diner said it was clear the two were more than just friends.

Another diner claimed Anderson couldn't keep her hands off of Don Jr. "I guess they're not trying to hide it. They've been seen together all over Palm Beach," a third onlooker said.

Usually, when Eric and Donald Trump Jr. go on safari, it involves a bunch of high-caliber weapons and ends with the slaughter of wild animals. However, safari nights at Mar-a-Lago were a totally different jam. Instead, they involved VIPs, elites, problematic billionaires, and politicians.

The Miami Herald revealed in September 2019 that Republican party fundraiser Li "Cindy" Yang had shilled Trump tourism opportunities to Chinese businessmen. They could kick back and network with Donald Trump and his gang if they splashed the cash. Yang sold the Mar-a-Lago galas online, offering packages from $1,000 for seats only to $10,000 for a two-night stay, with spa and golf course access thrown in. There was a black tie with leopard print dress code, and the gaudy gold ballrooms were decked out with paper cutouts of African game.

Safari nights sprung up in the wake of Donald's "very nice people on both sides" Charlottesville white supremacist comments. The usual Palm Beach social crowd jumped ship and canceled future engagements, paving the way for Yang and her wheeling-dealing clients. It was a controversial arrangement, to say the least. "This is the first time I've heard of sitting presidents and their homes being put on tour," June Teufel Dreyer, a University of Miami professor of political science, told The Herald. "I think it's definitely new for China. I don't think this was done for Ronald Reagan or even somebody who was very nice to the Chinese like Barack Obama."

One of the Trump family's biggest controversies in Florida was the Mar-a-Lago raid. Donald Trump has never been one to abide by the rule book, so few should have been surprised that he flew close to the legal flame during his presidency. However, unfortunately for 45, he flew way too close, resulting in the Feds knocking down his door in August 2022.

The FBI was looking for classified documents that Trump took to Mar-a-Lago with him after vacating the White House in January 2021. After the National Archives and Records Administration discovered that a bunch of potentially sensitive classified docs from Trump's presidency were missing, they demanded he hand them over. After multiple requests, his attorneys complied — partially. In May 2021, they gave up 15 boxes. In June 2022, they handed over 38 more docs. However, after concluding the total still fell short, the Feds were summoned. They found more than 100 additional papers during their raid. "My beautiful home, Mar-A-Lago in Palm Beach, Florida, is currently under siege, raided, and occupied by a large group of FBI agents," Trump announced in a statement (via CNN).

In June 2023, Trump was indicted on 37 felony counts relating to the mishandling of classified documents, obstructing justice, and making false statements. However, a Florida judge dismissed the case in July 2024 after ruling the appointment of Special Prosecutor Jack Smith was unconstitutional.