Caught in a bad bromance.

Photographer: PETRAS MALUKAS/AFP/Getty Images

So What About Trump's Bromance With Putin and Russia?

Timothy L. O'Brien is the executive editor of Bloomberg Gadfly and Bloomberg View. He has been an editor and writer for the New York Times, the Wall Street Journal, HuffPost and Talk magazine. His books include "TrumpNation: The Art of Being The Donald."
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Several years ago during a lengthy deposition taken as part of a lawsuit Donald Trump filed against me, he explained why he didn't want to provide details about a possible hotel deal that he said he and his son, Donald Jr., were orchestrating in Russia.

"I wouldn't want you to go and tell anybody about it because it would possibly mess up the deal," he said. "And it's a big deal."

The terms of the deal seemed sweet. Trump said he'd get a 20-to-25 percent ownership stake in the hotel, plus management fees, without having to plunk down a dime. "I was going to invest nothing," he said.

Trump said that he didn't think Russia presented undue financial risks, and that he was committed to the country. "It's ridiculous that I wouldn't be investing in Russia," he said. "Russia is one of the hottest places in the world for investment."

My lawyers were deposing Trump in late 2007 to examine his claims that my biography, "TrumpNation," had damaged his business prospects in Russia and elsewhere. (Trump lost the case.)

"I would say that we will be in Moscow," the future GOP presidential nominee continued. "It will be one of the cities where we will be."

Today, Russia looms large once again in the Trump narrative.

Trump spent the past week unfurling a crazy quilt of descriptions of his relationship with Russia's president, Vladimir Putin, culminating in an interview aired Sunday on ABC's "This Week," during which he said several times that he has “no relationship" with Putin. He said he “never met” Putin and had “never spoken to him on the phone.”

Huh?

As NBC has pointed out, Trump told the network in an interview three years ago that he had "a relationship" with Putin. And as Talking Points Memo has noted, Trump told the National Press Club in 2014 that he had visited Moscow and had talked "indirectly and directly with President Putin, who could not have been nicer."

Trump has also gone out of his way to praise Putin for years, saying that the Russian leader was "highly respected within his own country and beyond"; that "Russia and the United States should be able to work well with each other towards defeating terrorism and restoring world peace," and that "I would probably get along with him very well." When Putin was criticized for allegedly ordering Russian journalists to be murdered, Trump defended him by saying "I think our country does plenty of killing also."

Trump's interview with ABC on Sunday came on the heels of a press conference in which he invited Russian hackers to poke into the e-mail accounts of his presidential rival, Hillary Clinton. (He walked back the suggestion a day later, saying he was just "being sarcastic.") Trump has also toyed publicly with breaching the NATO alliance by abandoning Eastern European countries neighboring Russia.

All of this back and forth about Putin, Russia and hackers has prompted speculation about the actual depth of Trump's Russian interests. That, in turn, has prompted Trump to say that he has no business in Russia:

Donald J. Trump @realDonaldTrump
For the record, I have ZERO investments in Russia.
Twitter: Donald J. Trump on Twitter

Despite such statements -- and Trump's belated denial of a bromance with Putin -- the U.S. media remains in full conspiracy-theory mode. In recent days, the press has made much of Trump's ties to Russia, suggesting that the candidate is quietly working with Putin to further his international business interests.

Unlikely.

Conspiracy theories need a theory, and if there's one thing that's been missing for decades from Trumplandia, it's a theory. In life, business and politics, Trump operates by the seat of his pants. In years of covering him, I've yet to see him demonstrate the discipline needed to engineer a sophisticated, consistent, long-term strategy.

It's also useful in moments like this to remember that Trump is not a blue-chip, Fortune 500 business titan. His business is built around reality TV stardom, licensing, and lucrative stakes in a handful of buildings and golf courses. Despite decades of talk about grand Russian plans, Trump has never built anything in the country. He once staged a beauty contest there and unsuccessfully begged Putin to attend. That's it.

Trump does have a history with Russia, though it's one that has been opportunistic, improvisational and largely fruitless.

The Republican candidate made his initial trip to the country in the summer of 1987, when it was still under communist rule. He went at the invitation of Yuri Dubinin, the Russian ambassador to the U.S. at the time, traveling with his first wife, Ivana, and the couple's two assistants. The group looked at about a half-dozen possible hotel sites in Moscow, mostly around Red Square. Trump said he stayed in Lenin's former room, Suite 107, at the National Hotel.

Nothing came of the trip. Ed Koch -- New York City's mayor at the time, and a longtime Trump nemesis -- used the episode to bait the developer: "How bright do you have to be to know that in Moscow you can't own property? How bright?"

Trump told Playboy magazine in a 1990 interview (when he was on the cusp of personal bankruptcy) that the reason his Russian deals faltered was because the country was "out of control and the leadership knows it." But Trump also praised the Russians for being "much tougher and smarter than our representatives."

In 1996, Trump (while still sorting through a string of corporate bankruptcies) made another Russian foray, announcing that he would erect a version of Trump Tower in Moscow. It didn't get built.

Several months later he entered the bidding to renovate two major Moscow hotels, traveling to the city to promote the projects. At the same time in New York, Trump was touting the idea of building a giant statue of Christopher Columbus on the banks of the Hudson River -- a project he said was being co-sponsored by the Russian government. None of this came to pass.

Trump then re-upped several years ago, saying he was plunging back into Russia with plans to build high-end residences around the country. Those never got built either.

Trump did build one successful project with Russian and other Eastern European partners -- but it was in New York. Working with a team that included the Bayrock Group -- a small firm based in Trump Tower and controlled by Tevfik Arik, a former Soviet official, and employing Felix Sater, a Russian with a sordid past -- Trump launched the Trump SoHo in 2010. Although the hotel bears Trump's name, the actual owners only gave Trump an 18 percent stake in it -- plus a licensing fee for his name and a management contract to run the hotel. (Trump later settled a lawsuit alleging that he and his children hyped sales figures for the project to the media and prospective condo buyers; the Trumps denied any wrongdoing.)

Donald Trump, Jr., who traveled to Russia on his father's behalf during this period, spoke publicly about the money flowing into the Trump Organization from Russia. "Russians make up a pretty disproportionate cross-section of a lot of our assets; say in Dubai, and certainly with our project in SoHo and anywhere in New York," he told attendees at a New York real estate conference in 2008. "We see a lot of money pouring in from Russia."

But when the Trumps talk about money "pouring in" to their relatively modest business from places like Russia, they're talking about wealthy homebuyers looking for the security of an overseas asset, a pied-à-terre, or a place to hide ill-gotten gains -- a phenomenon familiar to all high-end developers and to all global locales such as New York and London. Sure, some Kremlin money may be mixed up in all of that. But is it a pipeline funneling so much cash back and forth between the U.S. and Russia that it gives Trump special traction in Moscow? Nyet.

Despite a lack of any tangible signs of success in Russia itself, Trump has kept an eye on the country -- largely, I think, because it's an easy place to raise cash if you're a certain kind of free-wheeling, financially needy developer who doesn't like to ask a lot of questions of his business partners.

In late 2013, a state-controlled Russian news agency quoted Trump as saying that he had resurrected the idea of building a Trump Tower lookalike in Moscow and that he was "in talks with several Russian companies" about the project. It hasn't been built. Trump also staged his Miss Universe beauty pageant in Moscow that year, and pined on Twitter for one prominent guest to join the festivities:

Donald J. Trump @realDonaldTrump
Do you think Putin will be going to The Miss Universe Pageant in November in Moscow - if so, will he become my new best friend?
Twitter: Donald J. Trump on Twitter

During one of the GOP debates last fall, Trump repeated a tale about how, once upon a time, he and Putin had become well-acquainted "stablemates" after appearing on a segment of "60 Minutes" together. As it turns out, he had no opportunity to get to know Putin during the show because the two men were filmed continents apart.

Financial disclosure forms Trump filed with the federal government earlier this year don't appear to show any current Russian holdings (although the filings did list licensing, hotel, golf and other business operations in the former Soviet republics of Azerbaijan and Georgia.)

Trump could settle some of the speculation around his financial ties to Russia by releasing his tax returns. Thus far, he's balked.

In the meantime, the real danger in this political season isn't that Donald Trump knows Vladimir Putin well (which he doesn't), or even that he has dark ties to Russia. It's that Trump is running his foreign policy shop in the same way he ran his business in Russia over the years: as improv. Putin, on the other hand, is playing the great game.

This column does not necessarily reflect the opinion of the editorial board or Bloomberg LP and its owners.

To contact the author of this story:
Timothy L. O'Brien at tobrien46@bloomberg.net

To contact the editor responsible for this story:
David Shipley at davidshipley@bloomberg.net