Marty Latz

Opinion contributor

President Donald Trump’s weak negotiation skills have now led to the longest government shutdown in U.S. history. And his negotiation strategies — including his proposal Saturday to link wall funding to temporary legal status for "Dreamers" — are making it far less likely that it will end with a deal that accomplishes his goal of funding a border wall.

How did this happen to a self-proclaimed master deal-maker who was elected partially on the notion that he was, as described by his campaign manager Corey Lewandowski, “the greatest deal-maker our country’s ever seen”?

It didn’t happen overnight. Despite his best-selling negotiation book, "The Art of the Deal," and his NBC hit series, "The Apprentice," both of which portrayed him as a great negotiator, his business negotiation skills and strategies never lived up to the hype.

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I’ve been studying and teaching negotiation for 25 years, and I have analyzed more than 100 Trump business deals to evaluate whether his skills and strategies align with the experts’ proven research.

Here’s the real deal: Trump negotiated some great deals early in his career, including Trump Tower and the redevelopment of the Commodore Hotel (now the Grand Hyatt).

He negotiated these in part by using proven techniques, including extensive preparation, aggressive goals, a comprehensive understanding of leverage, and highly adversarial tactics that can work well in zero-sum competitive New York real estate negotiations with counterparts with whom you don’t care about a future relationship.

But then Trump became a celebrity in the mid-1980s and stopped using many of these techniques. This led to multiple poor negotiations in which he overpaid by tens of millions for various assets, including the Eastern Air Shuttle and the Plaza Hotel.

These disastrous negotiations in part led to his multiple business bankruptcies. In 1990, an independent financial analyst found Trump owed $3.2 billion, more than $800 million of which was personally guaranteed, and had a net worth of minus $294 million.

Bottom line: Trump was never a great business negotiator.

Trump started using these same ineffective negotiation strategies immediately upon his inauguration, and they caused major problems, as presidential negotiations require vastly different strategies to be effective.

What was his first big presidential negotiation — and a precursor to his current inability to negotiate wall funding from Congress? A canceled negotiation summit with then-Mexican President Enrique Peña Nieto on Jan. 31, 2017.

Trump blew Mexico summit in first month

This was Trump’s first opportunity as president to develop a constructive relationship with a partner that he needed to strengthen border security — his prime goal with a wall.

Yet Trump made numerous negotiation missteps here, foremost among them scheduling the signing of two executive orders on immigration (including one on constructing the wall) the same day his team first met with Mexican officials in the White House and just days before his summit.

This inflamed already high tensions between the two countries and, when combined with a Trump Twitter threat aimed at the Mexican president, led Nieto to cancel.

These moves reflected incompetent negotiation planning. Harvard’s Negotiation Briefings described the executive orders mistake as “a failure to coordinate a unified strategy within his administration.”

Coordinating large numbers of parties and issues is a major difference between Trump’s business and presidential negotiations. Such skills were just not in Trump’s negotiation tool kit.

Using Twitter to engage in high-stakes complex diplomacy through what appeared to be a wholly instinctive use of the limited characters of Twitter, seemingly without any review by his foreign policy experts, also proved highly counterproductive and damaging.

Four missed chances to negotiate wall money

Since then, Trump has failed to negotiate wall funding on at least four occasions, with these same missteps frequently reoccurring. Successfully negotiating any of these deals would have prevented the current shutdown:

►The United States had strong leverage in its “new NAFTA” negotiations with Mexico. Trump could have introduced wall funding there. Nothing wall-related is in this deal.

►Wall funding has consistently appeared as part of Trump’s negotiations with Congress over the Dreamers, undocumented immigrants brought here illegally as kids, since 2017 — when Republicans enjoyed House and Senate majorities. Trump failed to get wall funding or even a deal here.

►Trump had two years to negotiate comprehensive immigration reform with a Republican Congress that might have included wall funding. This never happened.

►Trump even could have negotiated some wall funding last month as part of a last-minute deal to prevent a shutdown before the Democrats took over the House. Though he might have had to make significant concessions given his weakening leverage, expert negotiators often compromise to accomplish their main goals.

Founding Father and President James Madison, a brilliant negotiator, engineered significant compromises during our Constitutional Convention. So did President John F. Kennedy in negotiating the end of the Cuban missile crisis. President Ronald Reagan also made concessions to Democrats to get his deals done.

Will Trump similarly compromise to end this shutdown? Perhaps. He would certainly point to his recent proposal as a significant move.

But his “new” proposal has been previously rejected by the Democrats. And its public nature made it appear more like a public relations gambit to change public opinion about who to blame for the shutdown and less like a real concession.

Public negotiating doesn't work in politics

In fact, one of Trump’s major mistakes has been to insist upon largely negotiating this in public and via Twitter. This has made it exponentially more difficult for anyone to compromise.

After all, any movement off their repeated public statements of inflexibility would likely be viewed as weak to their counterparts and constituents. None of the parties can afford this in their first negotiation in their current roles.

Trump also made any resolution more difficult with his changing positions and undermining his own negotiators and Senate Republican allies.

Of course, House Speaker Nancy Pelosi and Senate Democratic leader Chuck Schumer have also dug in their heels. But they have stronger leverage than Trump with a Democratic House newly empowered in part due to their opposition to his wall.

Democrats also enjoy strong leverage as the polls show the public mostly blaming Trump for the shutdown (Trump saying he would be "proud" to shut down the government weakened his leverage).

Trump’s repeated failure to negotiate wall funding for two years largely caused this shutdown. His recent missteps have extended it. Hundreds of thousands of government workers and contractors are now paying the price for his weak negotiation skills and ineffective strategies.

Marty Latz is the founder of Latz Negotiation, a national negotiation training and consulting company. His most recent book is "The Real Trump Deal: An Eye-Opening Look at How He Really Negotiates." Follow him on Twitter: @MartyLatz