The Truth About Trump the “Dealmaker”

Most of us who have watched his career over the years know this already, but apparently, a lot of people are under the impression Donald Trump is just one hell of a dealmaker. This is absurd.

First of all, he is not running a business, so even if he was skilled as a business dealmaker, that would not be at all helpful when running government. But look closely at his temperament, and what you find is someone who is extremely stupid and gullible, as well as petulant and incapable of compromise. How can anyone make a deal if they are completely strident and unable to compromise? The answer is, of course, they can’t.

If you think of Donald Trump as a great dealmaker, you’re not paying attention to how he’s handling the wall “negotiations” and the shutdown. Of course, it should have been obvious before then.

No one who is a “master negotiator” has to go into bankruptcy six times.

No one who is a “master negotiator” has to go overseas for investment money because no one in the United States will invest in him or lend him money.

No one who is a “master negotiator” has to make deals with the Russian government in order to win a presidential election.

Face it; when a “business genius” has debts that are greater than his assets (a requirement for bankruptcy – again, that happened six times!), something has gone wrong with his dealmaking. It is possible to be a good businessperson and fail at a venture, but Trump portrays himself as one of the “great dealmakers of all time,” even as his business failures piled up one after the other. Seriously, list them all;

  • Trump Steaks: failure
  • Trump Air: failure
  • Trump Mortgage: massive failure
  • Trump Vodka; failure
  • Trump Casinos: spectacular failure at making money from GAMBLING. Seriously, how does a “master dealmaker” not make money when people are quite literally giving it to you for nothing?
  • Trump: the game: failure
  • Trump Magazine: failure
  • Trump Travel ( huge failure
  • Trump Communications: never got off the ground
  • Trump Tower Tampa: he only sold his name to put on it, but the builders went under after taking hundreds of down payments on million-dollar condos and they sued Trump, who settled claims at pennies on the dollar.
  • Trump University: this crooked enterprise not only didn’t make him any money, but it ended up costing him a cool $25 million after the court ruled it a crooked enterprise. There are several relatively sketchy “educational” enterprises out there that escape scrutiny. It seems a “master negotiator” would be able to avoid scrutiny, as well.
  • Trump Foundation: Again, a “master businessman” should be able to figure out a way to use his foundation to mostly do good for people and occasionally dip into the fund when needed. Trump basically used his foundation as a slush fund. (A “master dealmaker” shouldn’t even need a slush fund, am I right?)

Does this look like the record of a master businessman and negotiator?

And that’s before he became an occupant of the White House. Now, he is screwing up on a much higher and more consequential level. Everything he does betrays him as a phenomenally shitty “dealmaker.” Consider his efforts to negotiate a treaty with North Korea, in which he got nothing in return for giving Kim Jong Un everything he asked for. The “agreement” he signed essentially that Kim and North Korea would someday discuss ending their nuclear program and someday discuss a treaty with South Korea, without actually agreeing to anything. As such, virtually every American intelligence agencies who monitor North Korea has said their nuclear program has expanded, despite Trump’s assurance that he and Kim are best buddies now. His trade wars with our allies and largest trading partners, including Europe, Mexico, Canada, and China, have done far more damage to the United States than anyone else, and his rationale for the tariffs demonstrate a complete lack of understanding of the very concepts of tariffs and trade, which would seem rot be an essential element of trade dealmaking. Almost weekly, he Tweets out exaggerated trade deficit numbers and insists that the country is “losing” that amount in trade. This is a complete misunderstanding of a core concept that any trade negotiator has to know. Millions of Americans MAKE money from the trade deficit because Asians and Africans can make things cheaper than we can. A lot of companies, including Walmart, Apple, and Home Depot, are making tons of money from the trade deficit. And wasn’t he recently bragging about the “miraculous” 4.1% GDP growth just before his trade war? How would that be possible, if our trade deficits were “losses”?

He claims to have “renegotiated” NAFTA into something he calls the USMCA, which most economists say is identical to everything that was part of NAFTA and the TPP, with nothing new added. His lame attempts to destroy the Affordable Care Act have been ham-handed and ridiculous, and thankfully, all have failed miserably and have shown him to be a terrible negotiator.

We also have his constant failures in the area of immigration. He lost his first several tries for a Muslim ban before finally passing one that didn’t completely blow up the Constitution. His “zero tolerance” policy essentially blocked thousands of qualified asylum applicants and separated children from their families, which indicates someone without the patience or the skill to go through just enough hoops to make sure the right thing is done. And now we have a government shutdown over $5.7 billion for a border wall. And though he is trying to blame Senate Democrats for this, the fact of the matter is, this is all about Trump and his inability to negotiate anything. Keep in mind, when he was trying to make a DACA deal in 2017, he had a deal that gave him a free-and-clear $25 billion for a wall. Now, thanks to his dealmaking skills, he is holding about 800,000 government workers and those who rely on their services hostage for one-fifth of that amount. Does this sound like a really good dealmaker to you?

Everything Trump does, he does with a sledgehammer. Many people think he has an elaborate plan to take over the country and the economy, or even to hand the democracy over to Trump and Putin, but the reality is, everything that is happening along those lines is the direct result of his inability to make a deal. He is certainly beholden to Putin and Russia for something; probably hundreds of millions or even billions of dollars in loans to keep the Trump Organization afloat.

Dealmaking requires people who are capable of understanding what every party to an agreement wants out of the negotiation. That means being able to fully understand every small detail; is there anything about Donald Trump that suggests he can absorb details on anything? Is there anything about him that indicates an ability to consider any other party’s wants or needs? A good negotiator can’t have ADD, and they have to be able to set reasonable goals and demonstrate an ability to be flexible and the aforementioned patience; several qualities that not only have not been demonstrated by Donny, but which he seems incapable of demonstrating.

Governing requires two qualities to be successful. The first one is the ability to compromise, which is not a weapon in Donny’s arsenal in any way. It also requires a desire to enact policy that helps the people he works for. Trump can’t do that. For one thing, after two years in the job, he still has no concept of what the job of a president entails. He truly seems to believe he’s the “Boss of America,” and that everyone works for him. Look at the degree to which he envies authoritarians. He truly wishes he was one of them. Even though he is obviously owned by Putin, he truly envies the Russian president and wants to be him. There is a reason why the Trump Organization has always been privately held; Donny is used to working without scrutiny and he likes doing “business” that way. And since he thinks the United States government is a “business,” the scrutiny he gets enrages him.

As for policy, forget it. Trump suffers from a complete inability to maintain interest in anything for more than few minutes, and that may be generous. Whereas the last two Democratic presidents could be described as a bit too “wonky” in many ways, Trump lacks any sense of the detail that would be necessary to develop policy. When he first came into office, you’ll recall his penchant for issuing one “executive order” after another. The reason he does this less so now is because he finally realized that the term “executive order” did not mean he was giving orders to everyone in the country and everyone was required to follow those orders.

This inability to craft or enact actual policy and his lack of understanding of the nuance of the job – or any kind of nuance in anything, really – places any “dealmaker” at a disadvantage because the people he intends to make deals with have at least some knowledge of the subject matter and they have an idea of what they want. Think about it; every time Trump has “made a deal” with Democrats in Congress, he’s reneged on it. And he has done so because someone told him he wasn’t getting what he wanted. If you’re a Manhattan real estate mogul, and you’re buying a condo building in, say, Tampa, but your only frame of reference is Manhattan, you’re not likely to be a success. Likewise, if you are in government and you are trying to enact policies regarding immigration, you have to know what is going on. And if you’re going to shut down the government in order to get money for, say, a border wall, you’d better know exactly what that money will be paying for. As of right now, Donald Trump just wants his way, like a toddler who demands his juice. He doesn’t care about the juice, really; he only cares that mommy gives it to him. Right now, Trump is demanding $5.6 million of our taxpayer dollars – money the government doesn’t even have, thanks to the GOP Tax Scam from 2017 – and he can’t even decide whether he wants a concrete wall or a steel barrier with openings. There is no rhyme or reason or a plan or anything in place; the giant orange toddler just wants his way.

If you still think of Donald Trump as a master dealmaker, you simply haven’t been paying attention. This is a man-baby with no ability to fashion any kind of long-term strategy on anything. He can’t even deal with his constituency, which is primarily made up of simple-minded people who just want their way, just like him. He appreciates his “base,” but he’s also scared to death of them and he is absolutely incapable of creating a strategy for placating them. Ohh, sure, there are the Trump cultists, but their numbers are shrinking, and will continue to shrink because there is nothing he can do to keep them. Consider this shutdown. When his “base” misses a check or two, especially the tax refund they’ve come to rely on every spring to buy the kids some new clothes or to take the family on a small vacation in the summer, another bunch of them will peel off. His party already suffered massive losses in November, at the federal and state level, and most of the candidates he endorsed lost. This is not someone capable of even making a deal with people who want to love the hell out of him. Again, this is not someone capable of making deals because he’s too childish and small to get one done.

The current shutdown over as relatively small amount of money earmarked for a wall that will likely never be built is a sign that the “master negotiator” sucks at the trait his cultish followers used as a rationale for voting for someone with no government experience. This is his shutdown and his alone. More importantly, his willingness to burn everything down to get what he (and almost no one else) wants is evidence that he is incapable of negotiation in good faith and it explains a lot about when his life in business was such a failure.

People who have to blow things up to get what they want are horrible negotiators because no one wants to deal with them. There are reasons why Trump couldn’t get a loan from an American bank, and why many contractors would not work for him. The reason the Saudis and Russians were buying up all his condos was because Americans didn’t want them. Contractors and workers often worked without pay and many contractors who did considerable work for him had to sue to get a fraction of what he was owed.

And you think this guy’s a great “dealmaker”? Well, come over here because I have this bridge to sell you…

Also published on Medium.

About Milt Shook

A writer with more than 45 years in the political game (and let's face it, it is a game). I am a liberal because facts have a liberal bias, and I really like facts. If you like facts, you'll like this blog. If not, you'll have a hard time.


The Truth About Trump the “Dealmaker” — 1 Comment

  1. One of the things that created the myth of Donald Trump as a great businessman was the show “The Apprentice.” There’s a great piece in the New Yorker on how the producer made Trump look good – even though he wasn’t. I kept trying to warn people back in 2016 that, aside from Trump being a lousy businessman for all the reasons you’ve stated, running a business is not the same as running a government.

    It’s even worse when you’re talking about coming from a privately held business instead of a publicly held one. Someone like him would have been canned years ago in a publicly-held one, where he would have had to answer to a board and stockholders. I’ve run two different businesses as a sole owner, and sure, it was great that I didn’t have to answer to anyone, or wait for permissions. However, I’ve also been an officer or on the board of various organizations, and in all of those, I had not just limits, I had to get permission and approval for things. It’s a different mentality, and it’s pretty obvious he can’t grasp it.