Donald Trump has hired lobbyists to advance his gambling interests in Florida, to boost his chances of building a massive convention hall in Long Island and to keep a hotel on track in downtown Chicago.

But for a man who runs a massive real estate operation, claims a personal net worth of $10 billion and has business dealings across the globe, Mr. Trump has been surprisingly circumspect when it comes to paying for influence.

Indeed, checks of states where the billionaire businessman and GOP presidential nominee has interests show only a few hundred thousand dollars, spread out across the states and years, spent on lobbyists by the Trump Organization. His last payment to a lobbyist at the federal level was 15 years ago.

By contrast, other big-name billionaires with companies named after them regularly shell out $1 million dollars a year.

Mr. Trump has, however, been an active player in donating to politicians, and regularly brags about splashing cash to both sides of the aisle in order to get what he wants.

And he’s also a master of the personal charismatic appeal — in essence becoming his own best lobbyist.

“It is very common for the CEO and executive to lobby personally on behalf of a variety of issues,” said Josh Stewart, deputy communications director for the Sunlight Foundation. “So it isn’t surprising that someone like Trump would forgo lobbyists and use his star power and checkbook to get influence and access.”

Mr. Stewart also said the political glad-handing is often harder to track given the patchwork of disclosure regulations regarding face-to-face meetings on the state, as well as the local, level, where looser lobbying regulations tend to exist.

“So there is a certain problem with disclosure where there may not be an actual paper trail,” he said.

Ironically, it’s that sort of influence-peddling that Mr. Trump says he’s running against in his presidential campaign, arguing that corporations and wealthy individuals have distorted the economy and left average Americans behind.

“I have joined the political arena so that the powerful can no longer beat up on people that cannot defend themselves,” Mr. Trump said at the Republican National Convention. “Nobody knows the system better than me, which is why I alone can fix it.”

In the states

Mr. Trump’s biggest lobbying investments have been in Florida, where he owns, among other properties, the Mar-a-Lago club in Palm Beach and the Trump National Doral, and he has been interested in loosening gambling restrictions for quite some time.

In 1998 Trump Hotels and Casino Resorts gave $50,000 to the Republican Party of Florida, and Mr. Trump followed that up in 2010 with a $10,000 donation to the state party and giving $125,000 to the Let’s Get to Work electioneering communication organization supporting Florida Gov. Rick Scott, a Republican, between 2012 and 2013.

In 2014 Mr. Trump also doled out $100,000 to the Republican Party of Florida, and his daughter, Ivanka, contributed $25,000 to the state GOP, as well as $500 to state attorney general Pam Bondi, a Republican.

Around the same time, Mr. Trump hired Brian Ballard, a powerful Florida lobbyist who was part of Mitt Romney’s national fundraising team in 2012 and Sen. John McCain’s in 2008.

“If Miami doesn’t do casinos, that would be a terrible mistake,” Mr. Trump told the Miami Herald at the time. “Taxes would be able to be reduced substantially, and Miami is the only place that Las Vegas is really concerned about — in the United States.”

From July 1, 2013, to June 31, 2015, Mr. Ballard’s law firm collected upwards of $580,000 to lobby the state legislature and executive branch on behalf of the Trump Organization, according to the state filings.

Mr. Ballard, who is now part of the joint fundraising operation between Mr. Trump and the Republican National Committee, said Mr. Trump’s lobbying investment is “within the middle range” for a real estate developer.

“It would be malpractice on his part not to have his interest represented,” Mr. Ballard said. “You would not want him as president if he did not protect his economic interest when he has so much at stake.”

Mr. Ballard also said Mr. Trump has cultivated strong relationships with state leaders.

“He is on a first-name basis with the past two House speakers, with the governor and the attorney general,” he said. “I don’t know one elected official who did not meet him and was not impressed, and that is not the same with every client.”

And he likened Mr. Trump’s appeal to that of former English footballer David Beckham, who has hired his firm to help him pave the way for a soccer team in the Miami area.

“He is second to David Beckham in celebrity appeal,” he said. “Whether you like him or don’t like him, he draws attention.”

But the lobbying efforts have so far fallen short in Florida, where the debate over gambling has been gummed up at the state level.

Mr. Trump has a limited lobbying record in his home state of New York — though he and his allies did get fined $250,000 in 2000 for failing to disclose that he bankrolled newspaper ads against casino gambling it the Catskills, fearful they could hurt his casino interests in Atlantic City.

More successful was Mr. Trump’s foray into Illinois, where he was seeking to pave the way for a hotel in downtown Chicago.

Between 2003 and 2008 he was represented by Advanced Practical Solutions and DLA Piper Rudnick, according to the Illinois Secretary of State’s lobbying database, as he sought to build a hotel and condo building in Chicago.

Around that same time, he was again more active on the campaign donation front, including $12,500 to the Cook County Democratic Party, $5,000 to a Chicago City Council member supportive of his project and $7,000 to then-Gov. Rod Blagojevich.

He also contributed $50,000 to future Chicago Mayor Rahm Emanuel during the final months of the 2010 campaign.

The donation came back to haunt Mr. Emanuel after the “TRUMP” sign started going up on the Trump Tower in Chicago, angering city residents and local columnists who called it “urban acne.” Mr. Emanuel’s critics wondered whether the Democrat was being silent because of Mr. Trump’s financial assistance, but Mr. Trump emerged unscathed.

“My guess is there is nothing illegal because of the nature of the local ordinances involving contributions from people with contracts, but it does raise conflict-of-interest issues,” said Kent Redfield, a professor at the University of Illinois at Springfield who runs the Sunshine Project, which aims to bring transparency to campaign finance.

“It is more an issue for the mayor than it is for Trump, because clearly Trump has said, when I give money to people, I expect things, which is not helpful to Emanuel, obviously,” he said.

Taking on the lobbyists

Given his history, Mr. Trump’s critics find it hard to believe he will be able to change the culture of Washington if he wins the November election.

“The Trump pitch on this is ‘I have been — by the standard I am annunciating now — unprincipled my entire life, but at 70 years old, you can count on me changing all of my attitudes and behaviors if you honor me with your vote,’” said Mac Stipanovich, a GOP strategist and Florida lobbyist. “The percentages of that being true are very low.”

With 25 years under his belt in the lobbying business, Mr. Stipanovich said his beef with Mr. Trump is not his push to protect his interest, but “saying things that [are] inconsistent with what he does.”

The Trump campaign dismissed the criticism.

“He has often acknowledged he was part of the broken system, albeit on the other side, knows it better than anyone and will therefore be able to fix it,” said Hope Hicks, a Trump spokesman.

Mr. Ballard, meanwhile, said he believes Mr. Trump’s efforts to reel in influence-peddling will be aimed chiefly at the federal government.

That’s an area where Mr. Trump has been surprisingly absent.

Data from the Center for Responsive Politics shows his last federal lobbyist payment was in 2001, when he paid $20,000. His biggest payment in their records was 1998, when he paid two firms $290,000.

By contrast, Bloomberg LP, the firm controlled by Michael Bloomberg, spent $400,000 on federal lobbyists in 2015, and Dell computers, founded by Michael Dell, regularly spends more than $2 million.

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