How Trump’s New York negotiating style landed him on the brink of impeachment

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President Donald Trump. | Spencer Platt/Getty Images

President Donald Trump has always viewed life through the prism of his next real estate deal, betting he can just bulldoze opponents into giving him what he wants. But Washington doesn’t work that way.

Now, as he battles an impeachment inquiry that sprang from his alleged attempt to bully a foreign leader, those who know Trump say it’s in large measure because he never made the switch from the brash, no-holds-barred New York businessman portrayed in “The Art of the Deal” to the president of a country governed by laws and norms of behavior.

“He’s used to getting what he wants and he’s a tough street guy,” said Billy Procida, a former vice president for the Trump Organization. “He’s been dealing with subcontractors his whole life. You know what it’s like to deal with subcontractors? They’re all terrorists. They all want more money for the job and then you’ve got to fight them and say, ‘OK, quid pro quo, I’m going to give you this, you do that, I’ll give you this, you do that, if you don’t do this, I’m going to do that.’”

The disjuncture between the table-pounding imperatives of New York real estate and the delicacies of international diplomacy helps explain, these people say, why Trump is having trouble understanding why his “perfect” phone call with Volodymyr Zelensky, the president of Ukraine, may have crossed a line.

“He does nothing without a quid pro quo,” said a former White House official. “Nothing. Whatever deal has got to be to his advantage.”

“He treats a lot of conversations and a lot of negotiations, including with foreign leaders, along those lines,” said another former White House official. “‘What is it that you want? Here’s what we want.’ How can we find a way to reach some kind of deal or accommodation where we both get what we want but in particular where I, representing the U.S., get what I want.”

These ex-officials weren’t at all surprised, therefore, to learn that Trump had asked Zelensky to do him a “favor” while nudging him to launch investigations of his political adversaries — a 30-minute conversation whose interpretation is at the heart of Democrats’ impeachment drive.

House leaders, led by Speaker Nancy Pelosi, have charged that Trump’s chat with Zelensky is evidence enough of “bribery” and “extortion” — their characterization of what the president said was a “perfect” phone call, and his Republican allies say is just the normal give-and-take of foreign affairs.

What’s more, Trump’s defenders say, his upfront negotiating style has its advantages.

“He’s very direct from the beginning about what he wants,” said a former administration official. “You’re not wondering about what he wants or what the end goal is. … [T]hen he’ll hammer at it, so it’s clear that the person understands it and then that every time he speaks to that person, it will be repeated until whatever goal is achieved.”

Trump’s win-at-any cost mentality has those who have worked or dealt with Trump guessing that the known occasions when he pressed for Ukraine to investigate his rivals — the July 25 call with Zelensky and several with his ambassador to the European Union, Gordon Sondland — aren’t the only times he did so.

“He would just never take no for an answer if he wanted something,” said Barbara Res, a former vice president for the Trump Organization. She expects him to try to horse-trade with Senate Republicans and threaten to torpedo their reelection efforts if they show signs of disloyalty during the impeachment inquiry.

Asked for comment, White House deputy press secretary Hogan Gidley said, “President Trump’s ‘style’ is exactly what provided lethal aid to Ukraine so it could protect itself from Russian aggression, while the so-called ‘no drama’ Obama ‘style’ only gave Ukraine blankets and pillows — leaving our international ally dangerously vulnerable.”

Trump’s never-say-die mentality

At times during his business career, Trump’s sheer persistence paid off — even on some of his worst deals.

Take his doomed gambling ventures: While most businessmen would have pulled out and quit, Trump persevered and personally made millions of dollars for the better part of two decades after all three of his casinos in Atlantic City had filed for bankruptcy in the early 1990s.

Trump, who has often cast his predecessors as weak leaders who got steamrolled by China, staked his claim to the presidency on that kind of ability to play a weak hand well. “I do deals. That’s what I do. I do really good at deals,” he told CNN in September 2015 as his fledgling campaign was just starting to get a serious look.

His past colleagues also see a pattern in Trump’s real estate days that has repeated itself throughout his time in office: He becomes obsessed with trying to do any deal quickly, and likes to assess how much he has to give in order to get something.

“A lot of it is using leverage to negotiate, seeking to bully and apply pressure and force concessions, and you see it in negotiations with foreign countries, especially with China and trade,” said one former White House official.

Trump has yet to consummate a trade deal with China, though there are signs that Beijing’s growing impatience with the on-again, off-again negotiations has led to concessions.

And the president’s defenders say his approach is responsible for some major wins, from browbeating NATO countries to increase their defense spending to negotiating the United States-Mexico-Canada Agreement, his revised trade deal with Canada and Mexico.

But Trump’s style has also clearly foundered with North Korea, which has continued to expand its missile and nuclear programs despite his alternating threats to incinerate Pyongyang or make it the next Singapore. His “deal of the century” between Israel and the Palestinians has yet to be unveiled, and Iranian leaders have so far resisted his entreaties to negotiate as well as his campaign of “maximum pressure.”

Then there is Washington, where the policy process often moves slowly and there are laws governing what officials can and can’t do and how regulations can be written.

Here, his operating style has caused problems.

As the head of an eponymous family business, Trump was accustomed to making almost every major decision. It’s been hard for him to adapt to the sprawling and sometimes willful federal bureaucracy, where decisions can get slow-rolled, altered or simply ignored as they filter their way down the organizational chart.

Officials have frequently boasted to reporters about how they’ve thwarted Trump’s whims, as with his orders to assassinate the president of Syria, or pull out of NATO, or build a border moat filled with snakes or alligators.

One of them — an anonymous senior official styling himself as the leader of a cadre of “adults in the room” within the administration —has even parlayed a New York Times op-ed touting his “resistance” into a book on the same subject.

Some foreign leaders — notably Japan’s Shinzo Abe — have learned to adapt to Trump by reading “The Art of the Deal,” which lays out his favorite negotiating and strategy tactics.

But others have learned, to their chagrin, that it can be surprisingly easy to persuade Trump to adopt their positions — only to discover later that his commands don’t always get executed.

After Trump tweeted in August that he had ordered U.S. companies look for an alternative to manufacturing goods in China, for instance, staffers told reporters that Trump hadn’t issued any official order, explaining that the president was only warning companies to pull back from China.

And his now-infamous decision to pull U.S. troops out of Syria during a phone call with Turkey’s president led to weeks of chaos, angry outburst from Republican senators, charges of betrayal by America’s Kurdish allies, and ultimately — military officials have hardly been shy about bragging — a partial reversal.

“He may say, ‘Yes, yes I agree’ and the day after when you go back to the White House, nobody has heard about it,” said Gérard Araud, who dealt with Trump when he was the French ambassador to the U.S. and is now SVP at communications firm Richard Attias and Associates. “There’s no instructions down to the bureaucracy to implement what the president says.”

Some have raised a different issue they found frustrating about working with Trump: The president doesn’t see the value of actually preparing for negotiations, which makes it hard for his foreign interlocutors to get traction on their priorities.

That accords with the testimony of Lt. Col. Alexander Vindman, the National Security Council official responsible for Ukraine policy. Vindman told House impeachment investigators that Trump ignored his briefing materials ahead of the call with Zelensky.

“He believes that everything should be solved at his level,” said one former official. “He doesn’t enter into the details.”

Some Trump allies defend his negotiating style as one perfectly suited to driving a hard bargain with foreign countries and leaders of the opposite party.

“People who are sissies and people who can’t take tough people say, ‘Oh he’s relentless,’ but you know who wins? The tough people win, the sissies lose,” said John Catsimatidis, a New York billionaire businessman who has known Trump for 35 years.

“I don’t think any negotiator would be a good one if they were just giving things away without getting things in return,” one former White House official said.

It’s exactly that mindset, however, that seems to have gotten Trump into trouble with the Zelensky call by linking cooperation with Ukraine to investigating the Bidens — and led top aides like former national security adviser John Bolton to call it a “drug deal.”

“There’s always an ask,” a former White House official explained when asked whether Trump had pulled a Zelensky-type move on other foreign leaders. “‘You do this’ and more than a suggestion that something will happen. … He very seldom listened without coming up with a ‘This is what I need you to do and I’m willing to give this to you if you do it.’”

Three people who know Trump or have dealt with him called him “transactional,” with one Middle Eastern ambassador to Washington saying that Trump’s negotiating style has filtered down to senior staffers who are “always bargaining” with their foreign counterparts.

Sometimes Trump’s wheeling and dealing with foreign counterparts takes familiar forms, albeit of the kind of corporate championing that is normally left to ambassadors and secretaries of commerce.

Trump has placed a particular emphasis on urging countries to sign lucrative contracts with flagship American companies such as Chevron and Boeing — deals he can then take credit for brokering, according to the Middle Eastern ambassador.

When Trump was a businessman in New York, many of his fellow real estate tycoons learned to avoid him at all costs, viewing him as erratic — an assessment that would doubtless ring true to other world leaders.

“No good comes from being too close to him,” said a New York real estate businessman who has dealt with Trump. “Because he’s so unpredictable and so opportunistic, it’s like having a gun that you never know if you point at it if it’s going to fire back at your own face so the strategy as far as I’m concerned is don’t engage. There’s no reason to engage.”

“He is entirely opportunistic, entirely inconsistent,” this person said. “There’s no predictability except his own unpredictability.”

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