CORRECTION: This article has been updated to reflect Florida’s expansive definition of an individual campaign donor, which can include an individual and that person’s businesses, so Trump’s contributions may have conformed to the law. An earlier version suggested the contributions may have exceeded the legal limit.

Donald Trump used his various companies to donate 10 times the individual limit to Charlie Crist’s 2006 gubernatorial campaign, a Huffington Post review of state campaign finance records shows.

The donations were all made on the same day through companies Trump owns. All told, Trump made nine contributions of $500 to Crist’s campaign on Aug. 25, 2005, for a total of $4,500. At the time, the maximum allowable donation in Florida from an individual or corporation was $500, a sum that Trump had already given Crist’s campaign as a personal donation in June of that year. Crist was attorney general of Florida at the time.

HuffPost first reported on three of the nine companies last month, and has since identified an additional six Trump companies that made contributions that appeared to exceed the individual limit. While Trump’s donations to Crist were legal under Florida law, it still raised eyebrows among good government groups.

“It’s pretty clear in this case that Trump was secretly buying influence without regard to the rules,” said Brendan Fischer, associate counsel at the nonprofit Campaign Legal Center.

Florida law defines “person” to include an individual, corporation, association, joint venture or company, so a person and that person’s entities each can contribute $500. Trump’s contributions masked his total giving, but don’t appear to violate state campaign finance laws in effect at the time.

The donations reveal the previously unknown scale of Trump’s giving to attorneys general in Florida, a state where Trump has a variety of business interests and a long record of legal problems. They also show that Trump’s apparent disregard for the spirit of campaign finance disclosure extends to long before 2013, when his charitable foundation made a now-infamous $25,000 donation to the campaign of Florida Attorney General Pam Bondi.

According to Fischer, Trump may have violated disclosure requirements, “which exist so that voters can see who is supporting a candidate.”

The newly discovered companies include Indian Hills Development; the Mar-A-Lago Club, Trump’s private club in Palm Beach; TIHT Commercial LLC, a holding company Trump registered at a non-existent office on Eighth Avenue in New York; 845 UN Limited Partnership, a company Trump used to develop a building in Manhattan in the 1990s; 220 Management Company, a holding company Trump operated for a building his father, Fred Trump, owned; and Trump International Golf Club LLC, a Trump golf course in West Palm Beach, 15 minutes from Mar-A-Lago.

All but one of the companies appear on Trump’s financial disclosure form, an accounting of a candidate’s financial interests that is mandated by the Office of Government Ethics. At the time Trump made the donations, he had a number of major projects underway in Florida whose success or failure relied on a friendly state government.

Christina Wilkie/HuffPost Donald Trump's campaign donations to Charlie Crist all appeared to come from separate companies. This list represents a number of them as they appeared in Florida state campaign finance databases.

In 2004, a year before the donations, Trump had signed a secret deal with developers to license his name to the Trump Tower Tampa, a luxury high-rise. Three years after the deal, in 2007, the developers abandoned the plans and declared bankruptcy — but not before Trump and his partners had collected millions of dollars in down payments from people who thought they were buying a dream home in Florida. The tower was never built.

As Trump was busy promoting the Tampa tower as “so spectacular that it will redefine both Tampa’s skyline and the market’s expectations of luxury,” he was also starting a new business venture, the Trump Institute, with Mike and Irene Milin. At the time, the Milins were already well known to state attorneys general for operating a series of get-rich-quick seminars across the country, and in 2001, Florida’s then-Attorney General Bob Butterworth forced the Milins and their company, National Grants Conferences, to sign an “Assurance of Voluntary Compliance,” a legal document assuring the state they would end their illegal marketing practices.

In 2005, the Milins and Donald Trump teamed up to create the Trump Institute, a live version of the online real estate classes that Trump and his team had been offering for a few months. Trump was optimistic that the new live-action seminars could sell a lot more of Trump’s brand to people through his licensing agreement with the Milins.

Eventually, the Trump Institute declared bankruptcy, and Trump’s own spin-off, Trump University, folded and was later sued by thousands of former students who allege fraudulent marketing.

A spokeswoman for the Trump campaign declined to respond to questions from HuffPost Monday about the donations. Crist, a former Republican, has since become a Democrat and backed Trump’s rival, former secretary of state Hillary Clinton.

According to Fischer at the Campaign Legal Center, the fact that Trump gave so much money so far ahead of Crist’s actual 2006 election “suggests that Trump wanted something more immediate from Crist as attorney general, rather than necessarily backing Crist’s gubernatorial run.”

Moreover, it does not appear that Trump was nearly as interested in the election of Crist’s successors in 2006 as he had been in supporting Crist’s burgeoning campaign for governor in 2005.

According to campaign finance records, Trump donated an equal amount to each of the two candidates vying to succeed Crist in 2006, Bill McCollum and Skip Campbell, effectively hedging his bets on the outcome of the race.

Trump has never made a secret of his willingness to leverage donations to political campaigns in order to further his business interests. During the Republican presidential primary, he bragged about how he used campaign contributions to sway politicians to back his interests. “When they call, I give. And you know what? When I need something from them two years later, three years later, I call them, they are there for me,” Trump said.

According to Fischer, “the reasons for buying influence in Florida are pretty clear in this instance. It’s clear that Trump had plenty of reasons to try to evade campaign regulations.”

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.