From NBC’s Domenico Montanaro
Donald Trump has never won elective office -- for any position.

Yet, from time to time, he likes to fashion himself as someone who could be president. And in the most recent NBC/Wall Street Journal poll, Trump, in large part because of his name recognition, has rocketed to second place among Republicans and the top choice among Tea Party activists.

We’ve seen this movie before.

Trump has flirted with presidential bids twice previously -- in 1987 and 1999. Both times he didn’t actually up and run, but what did go up was the buzz surrounding him and sales of whatever The Donald was pushing at the time.

A cover profile of him from the now-defunct George magazine in its February-March 2000 issue, when he was toying with a presidential bid in the 2000 cycle, is instructive.

“Nonetheless once every decade or so Trump begins reminding folks that millions upon millions of them would like nothing better than to have him as their president, and up rockets his public image—and his income,” wrote Christopher Byron, the story’s author. “Up go the sales of whatever ghosted autobiography he happens to have in stores at the moment, up go the rental values of his apartments, in come more day-tripping gamblers lured to his Atlantic City casinos—in short, up goes the market price of the most valuable, and promotable, possession Trump has: his name.

“Then, like Kenny Rogers character who ‘knows when to hold ’em, and knows when to fold ’em,’ he simply places his cards facedown on the table, sweeps his winnings into his lap, and exits the quadrennial poker game without ever showing his hand—namely, the obligatory audited personal financial statement, required of serious candidates, that would reveal how modestly wealthy, relatively speaking, he really is.”

In 1987, per George:

“[W]hen Trump’s book leaped onto the best-seller list for the next 48 weeks, Trump’s campaign for the presidency faded away until nothing remained but the smile of a Cheshire cat.”

And Trump in the profile all but admitted it was about the money.

“I’m the only one who makes money when he runs,” Trump said. “I got a fortune for the book I came out with. Also, I’m the highest-paid speaker out there. I’m making 12 speeches a year at $100,000 each.”

Trump said on NBC’s Today show this morning that he would welcome filing the required financial disclosure. But the George profile highlights the smoke and mirrors of Trump’s wealth. Of his ostentatious home in Palm Beach, FL, once owned by cereal magnate Marjorie Merriweather Post:

“[T]o save it from seizure by creditors as his business empire crumbled, he turned it into a kind of real-life Love Boat for status-hungry businessmen you’ve never heard of. Trump sells memberships to the place for $100,000 a pop, which is not a bad way to pay the bills.”

And:

“His ownership of the Plaza Hotel was stripped from him, he lost his mansion in Greenwich, Connecticut, and he even wound up having to turn his treasured Mar-a-Lago [the Palm Beach home] into a spa open to the paying public.”

How would this square in Iowa?
It’s well known that Newt Gingrich’s biggest hurdle with social conservatives is his multiple marriages. But Trump, not only has had his share of marriages, few of his competitors’ exes were as scantily clad. For example, in the George piece, there was “the arrival, midway through the meeting, of a half-naked fashion model wrapped in a towel about the size of a dinner napkin, who approaches the two of us and joins the discussion.”

That woman was then-Melania Knauss, whom “Trump paraded around as his potential first lady.” They broke up, per the story, but she is now Trump's wife. He touted her as a “supermodel,” when “in reality,” she was “represented by a modeling agency owned by Trump.” Knauss’ rate doubled, and “20 percent of her modeling fees go to Trump, who also collects another 20 percent from agencies and publishing companies that hire her.” He “pocked 30 percent” of his second wife, Marla Maples’, brief stint as a Broadway actress.

He’s certainly not likely to win over women, not just with his prior marriages or his management of their modeling and acting careers, but then there's this quote in George about a woman who appeared in his house en route to the spa: “That bitch had some nerve, the way she treated Ron Perelman.”

(The woman was Patricia Duff, described by New York magazine as a political activist, who was Perelman’s third wife. Their marriage dissolved in a messy divorce.)

If that’s not enough, of course, Trump’s most well known for his involvement as a casino owner -- “the source of most of the cash and calamity in his life over the past 20 years."

Or his owning “a 282-foot yacht that had previously belonged to Saudi Arabian arms dealer Adnan Khashoggi.”

Or his general self-absorption, penchant for exaggeration, and self-aggrandizement, including a wall of magazine cover devoted to himself in his New York office, and even an oil painting of himself that sits in the Palm Beach home, which George described this way:

“[T]he Trumpster is tricked out in a white tennis sweater, with his mop of sandy hair tousled as if he’d just come in from a love game, set, match with Rudy Valle.”

Or his “various properties” that “slid into bankruptcy, and he was forced to sell his yacht as well as his airline….” He defended the bankruptcies on MSNBC’s Daily Rundown: “I never went bankrupt,” Trump said, trying to draw a distinction between personal bankruptcy and putting a company into Chapter 11. “Many of the biggest people in this country, many times have filed Chapter 11s on various companies in order to reduce debts.” He added, “I’ve done an unbelievable job” and used the laws of the country to help his companies.

The George story points out:

“[T]he siren song of the slot machines and craps tables was also the reason for his collapse into a prepackaged bankruptcy reorganization—from which he emerged as only a minority owner in a business he once owned outright. The fiasco in Atlantic City also led to the bank-directed reorganization of his real estate holdings, reducing him to little more than a manager of buildings he once owned.”

The line of using the laws is an old one, according to the George story, which pointed out his private plane was “registered in the offshore tax-haven domicile of Bermuda.” Trump responded: “I play by the rules, and the rules say I can keep a plane in Bermuda, so I do.”

Trump says his wealth is really wrapped up in real estate. But a Trump executive, quoted in the George story, via the book “Lost Tycoon,” said:

“It was all a shell game. We never had any unencumbered cash. We were always creating new partnerships and corporate entities to shift the money around. We were always robbing Peter to pay Paul.”

Case in point, in order to make it easier to borrow money, George wrote:

“Trump had his organization prepare a bogus net worth statement that pegged his net worth to $3.7 billion by wildly inflating the value of his assets, and then circulated it to the press. The ploy helped convince Fortune to proclaim him an authentic billionaire that autumn, and that in turn helped him secure the financing to buy the Eastern Airlines Shuttle and, thereafter, the Taj Mahal.”

For the record, Forbes, George wrote, said his net worth was likely $1.6 billion when the profile was written, but “much of his wealth s not from his own wheeling and dealing, but simply represents the Queens, New York, apartment buildings he inherited from his father, Fred.”

The conventional wisdom is that Trump would benefit financially from yet another flirtation with running for president. But as public-relations guru Jack O’Dwyer warned in the George piece:

“Publicity is like a football. You never know which way it’s going to bounce next. One false move and he could have the whole country laughing at him.”

Considering Trump’s doubling down -- to use a casino term -- on birtherism, it’s a very real possibility this time around that the third time won’t be the charm.