Years before he cozied up to Florida Attorney General Pam Bondi, Donald Trump attempted to make similar inroads into the state’s top law enforcement office.

On Oct. 3, 2006, the real estate mogul cut a $500 check to Walter “Skip” Campbell, the Democrat running for attorney general, according to campaign finance reports. Twenty-five days later, he reversed course, writing a $500 check to Campbell’s Republican opponent, Bill McCollum. As the election neared and McCollum’s prospects brightened, Trump gave a $1,000 check to the pro-McCollum group Citizens Speaking Out Committee, Inc.

Three years later, when McCollum was making a run for governor, Trump was once again there to help. In January 2010, he held a $500-per-head fundraiser for McCollum’s gubernatorial campaign at his posh resort, Mar-a-Lago.

The Huffington Post A fundraiser that Donald Trump hosted for Bill McCollum in 2010.

The money that Trump gave McCollum was dwarfed by the $25,000 his foundation contributed to Bondi before she opted not to join a lawsuit against Trump University. But it still illustrates a side of Trump that has complicated his run for the presidency. His contention that Democratic nominee Hillary Clinton engages in pay-to-play politics has been undermined by his own history of deploying his vast financial resources and celebrity to influence politicians. This was especially true in Florida.

“I would consider Trump to be a fairly significant player in politics,” said Ron Book, a longtime Florida lobbyist. “Any notion that Trump didn’t directly communicate with a broad array of Florida political figures over the last decade would just be misleading the public.”

By the time Trump hosted McCollum at Mar-a-Lago, his university and a seminar program to which he’d lent his name ― The Trump Institute ― were earning reputations as fraudulent enterprises. And numerous complainants were asking the attorney general’s office, which McCollum headed, to help them recuperate money.

McCollum told The Huffington Post that he was personally unaware of the complaints, saying the cases were likely handled by consumer protection officials. But the issue wasn’t exactly hidden from public view. In May 2010, the New York Daily News reported that McCollum’s office was looking into the complaints. His office ultimately never took legal action, passing the matter along to Bondi.

McCollum said he never talked to Trump about the seminars, nor did Trump ever press him for legislative or business favors at Mar-a-Lago or when the two met separately at Trump Tower in New York. The meetings, instead, were geared toward building a fairly common type of political relationship: McCollum wanted financial support and Trump, he imagined, wanted access.

“I was aware of the fact that he was a businessman and prominent,” McCollum said, noting that he had to run against a wealthy self-funder in current Florida Gov. Rick Scott (R). “It didn’t make him a special target for me. But it would show me as a candidate that he had the means to contribute and was known to make contributions. So I hoped he would contribute to me.”

“I’m not surprised that he contributed to both sides, to [Walter] ‘Skip’ [Campbell] and me both in that ‘06 race,” McCollum went on. “A lot of people do that. Especially businesspeople who didn’t have a particular passion for one political party or another. They were hoping to get an audience.”

Michele Eve Sandberg/Corbis via Getty Images Donald Trump and Florida Attorney General Pam Bondi attend the Palm Beach Lincoln Day Dinner at Mar-a-Lago, Palm Beach, Florida.

As his business empire expanded through Florida, Trump pursued an audience and favors in many venues. In addition to backing multiple attorneys general, he donated to state senators, governors (Jeb!), lieutenant governors, and House members. He used affiliated companies to skirt donation limits. And his contributions occasionally followed Florida politicians outside the state. When Bondi took over as chair of the Republican Attorneys General Association in 2014, for example, Trump made a $5,000 donation to the group.

Trump often operated at the intersection of business and government. Starting in 2013, he began employing a high-powered lobbyist in the state. And around that same time, he turned Mar-a-Lago into a fundraising base, hosting events for Republicans in its ballrooms year after year. By 2016, he was bragging about how much money he’d brought in for local party hacks.

“Nobody would have believed this five or six years ago,” Trump said in his speech before Palm Beach County Republicans. “We started, what, five years ago? And we were sort of on the poverty level at that point, right? We weren’t like this … My hand is falling off. I’m taking picture after picture after picture. Hundreds and hundreds of pictures. I was just telling Pam [Bondi] they’re getting $25,000 a picture and I’m getting nothing, right? This wasn’t like that five years ago, was it?”

Trump hasn’t shied away from his history of political donations. On the presidential campaign trail, he’s openly conceded that he gave to politicians for the purpose of currying favor. What’s underappreciated, however, is the extent of the favors he tried to curry.

In Florida, Trump wasn’t just trying to fend off investigations into his for-profit university. He was invested in building golf courses and constructing buildings; securing tax breaks and defying landscaping regulations around the properties he owned.

And he wasn’t above petty squabbling to get his way. Asked about Trump’s reputation, one Republican operative told HuffPost: “It’s very mixed. A lawsuit a day.”

Mar-a-Lago was the site of one such infamous fight. In October 2006, Trump and Palm Beach officials battled over the installation of a giant American flag on the property. As Politico reported in detail, the town fined Trump $250 a day for as long as the flag stood, saying it violated ordinances. Trump took the battle to Nancy Grace’s TV show before using his favorite weapon ― the lawsuit. He sued the city for $25 million.

Trump eventually dropped the case after the city agreed to drop its fines. He was allowed to have a slightly downsized flag and said he would donate $100,000 to veterans charities.

These kinds of squabbles weren’t an aberration. In Doral, a city of 50,000, trouble started when Trump bought a golf course in 2012. He whined about the condition of utility poles around the property and complained on Twitter: “In my opinion, one of the worst utility companies in the country is Florida Power and Light.”

In my opinion, one of the worst utility companies in the country is Florida Power and Light. — Donald J. Trump (@realDonaldTrump) October 8, 2013

Trump also went to war with homeowners who lived around the course. He thought their $500,000 homes were enough of a blight that in the process of renovations, he planted a dense wall of palm trees around the course. “What happens is when you are on, as an example, the first green on the golf course, you are staring at houses with laundry hanging out their window in some cases, he said at the time. “It’s not appropriate for the finest resort in the country.”

The neighbors, who prized the view of the famous course, complained to Doral officials, and Trump and Co. alleged that some trees had been damaged or chopped do. One resident claimed her backyard had become a dumping ground for golf course refuse that attracted rats.

But Trump was undeterred. He hired the law firm of a former U.S. Attorney for the state to individually sue eight residents.

And he didn’t stop there. In late October 2014, Trump gave a $5,000 check to a group called Citizens For a United Doral. The group was a small-time shop, taking in checks totaling all of $130,000. Its principal, Gustavo Garagorry, refused to answer questions about what he exactly did.

But Sasha Tirador, a political consultant with GR Strategies, the firm that was paid to do much of the group’s work, revealed that it was involved in one local race in particular: a city council contest between the incumbent, Bettina Rodriguez-Aguilera and a former councilman, Pete Cabrera.

Why would Trump be interested in this race? Rodriguez-Aguilera had not voted for a budget that would have included $2.5 million for the Miss Universe Pageant, which Trump ran at the time. But, in addition to that, she had sponsored a bill to help the 250 or so “angry residents at City Hall who lost scenic views of golf courses after billionaire Donald Trump planted giant areca palms between their yards and his golf courses,” according to the Miami Herald.

Cabrera won the election.

When contacted by HuffPost, Rodriguez-Aguilera was shocked to learn about Trump’s involvement with Citizens For a United Doral. “[Trump] had done a lot of negative things to our residents,” she explained, saying her opposition to him was just. “Those were the right things to do at that time.”

Marta Lavandier/ASSOCIATED PRESS Donald Trump at his golf course in Doral, Florida, on March 6, 2016.

Ultimately, Doral bureaucrats investigated the palm tree issue and found there were gopher-sized holes in the city’s landscaping ordinances. The trees were legal and the city eventually worked out a compromise with the golf course, which Cabrera helped negotiate.

“I think it’s safe to say he won no fans around his resort by ringing it with palm trees,” said Evan Owen, the communications manager for the city of Doral. “The city amended its landscaping code to prevent repetitions of this.”

The dispute over the palm trees wasn’t without fallout, though. Doral officials had been planning to give Trump a key to the city, but balked as his golf course renovations caused public backlash. Doral Mayor Luigi Boria, who had favored awarding a key, backtracked. “Trump doesn’t deserve my key” he said.

But by that point, Trump had enough clout to get his superficial recognition (he let it be known that he was “thinking about moving his whole corporate office to Doral”) ― and enough political support, too. The mayor reversed course again, a few days after the Miss Universe Pageant was hosted in Doral. The city council took up a motion to consider awarding the key, and the member who introduced it was none other than Cabrera.



Trump is “more than deserving of a key,” he said.

This past month, Cabrera helped beat back a measure that would have reassessed property taxes on Trump’s Doral golf course. Cabrera and the Trump campaign did not return a request for comment.

Editor’s note: Donald Trump regularly incites political violence and is a serial liar, rampant xenophobe, racist, misogynist and birther who has repeatedly pledged to ban all Muslims — 1.6 billion members of an entire religion — from entering the U.S.