Story highlights

Trump has slammed Wall Street -- particularly hedge fund managers -- as a special-interest group corrupting the political system

Trump's attack lines on Wall Street are boosting his "outsider" image

Last week, he unveiled a tax plan that would make certain wealthy investors pay higher taxes

New York CNN  — 

Donald Trump is a member of New York’s ultra-elite, with a massive real-estate empire, a multibillion-dollar fortune and a coterie of high-powered friends that – he has boasted – includes celebrities, athletes and foreign leaders.

But there’s a segment of Manhattan’s upper crust that Trump conspicuously sneers at: Wall Street investors.

Since launching his White House campaign in June, the Republican frontrunner has slammed Wall Street – particularly hedge fund managers – as a special-interest group corrupting the political system. Last week, Trump unveiled a tax plan that would make certain wealthy investors pay higher taxes.

Politically, Trump’s attack lines on Wall Street are boosting his “outsider” image in an election cycle where the establishment candidates are struggling to dominate.

But it’s also personal. For the boisterous New Yorker, these attacks are shaped by Trump’s belief that his work in real estate — a career that’s brought him immense wealth and is funding his presidential bid – is superior to that of financiers he likes to refer to as the “Wall Street guys.”

RELATED: Donald Trump unveils plan to slash taxes for the poor – and the wealthy

Speaking at a high school homecoming in Urbandale, Iowa, last month, Trump urged the crowd of teenagers gathered around him to pursue professions they feel passionate about – just as he did.

“You know, the thing with real estate – you can grab it, you can touch it, you can hug it,” Trump said, grasping at the air with his fists. “You can say, ‘Oh, this building is so beautiful! It’s paying me all that rent!’”

The guys on Wall Street? “In all fairness, it’s just like, paper. It’s paper,” he said, this time shuffling the imaginary paper in front of him with little enthusiasm. “It goes across the desk. It can be great but it’s paper. It’s not the same thing to me.”

RELATED: Trump: TV ratings ‘collapse’ without me

But the candidate’s Wall Street-bashing also obscures the reality that his real-estate empire couldn’t exist without a financial and banking system run by the very people Trump seems to look down upon.

Cliff Asness, a founding principal at AQR Capital Management, slammed Trump’s diatribes as “populist canard.”

“One can’t help but wonder: Does Donald Trump actually still build things?” Asness wrote last month in the City Journal. “Or does he mostly just license his name to things – another form of paper pushing? Yes, I’m saying to The Donald, you didn’t build that Trump eau de toilette.”

Trump’s net worth consists of around $4.3 billion in wholly owned Trump properties and real estate, over $3 billion in real estate licensing deals and brands and some $300 million in cash and marketable securities, according to the Trump campaign’s estimates as of last year.

RELATED: Polls: Trump still tops in Iowa, New Hampshire

“He’s a high-finance guy too. And look, there’s nothing wrong with that,” said conservative economist Stephen Moore, a well-known figure in New York’s financial elite. “His book was ‘The Art of the Deal.’ The people who make these deals and put together these multibillion-dollar financial transactions – that’s an important part of how American capitalism works.”

The Trump campaign declined to comment for this story, but long-time associates of Trump say the candidate’s open hostility to Wall Street in part has to do with the pride Trump takes in his line of work – turning blueprints and visions into physical, permanent structures made out of concrete, stone and glass.

“He’s very proud of the fact that he’s a builder and that the things he builds are indelible,” said Roger Stone, a former adviser to Trump’s presidential campaign who has known the businessman for decades. “He knows all the Wall Street guys, gets along fine with them, but he is not the toast of Wall Street.”

Trump entered the construction world as a young man, long before his family name was widely featured on luxury hotels, high-rise apartment buildings and casino properties around the country.

In one of his many books, “Think Big,” Trump says he inherited a passion for construction from his father, a real-estate developer.

“In truth I am dazzled as much by my own creations as are the tourists and glamour hounds that flock to Trump Tower, The Trump Taj Mahal in Atlantic City, 40 Wall Street or any of my own properties,” he writes. “Creating extraordinarily beautiful buildings really excites me and drives me to overcome the greatest obstacles.”

Last week, Trump crystalized his animosity towards Wall Street in a newly unveiled tax plan that would abolish the carried interest loophole, a provision in the tax code that allows some investors to pay significantly lower taxes on certain profits.

RELATED: The Donald Trump hedge fund crackdown that wasn’t

Trump said closing the carried interest loophole was “psychologically” significant.

“When you have a hedge fund guy who’s making $200 million a year and … he’s paying a very low rate of taxes, it’s not fair,” he told CNN’s Erin Burnett last week. “It tells people a lot and it’s got to end.”