Donald Trump knows he's in serious trouble

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60. MaddowBlog-Trump's self-declared reputation as a world-class dealmaker continues to collapse

As Iran backed away from the negotiating table, one longtime observer raised an underappreciated point: “Trump is perhaps the world’s worst negotiator.”

As Iran backs away from the negotiating table, it seems like a good time to highlight an underappreciated fact:

Trump is a spectacularly bad negotiator and dealmaker - and has been for years - Republican hype notwithstanding.
www.ms.now/rachel-maddo...

— Steve Benen (@stevebenen.com) 2026-06-02T18:05:39.412Z

https://www.ms.now/rachel-maddow-show/maddowblog/trump-deals-iran-negotiations-really-dont-care-very-boring

Nearly two weeks after Donald Trump boasted that a “peace” agreement with Iran had been “largely negotiated,” and the world could expect to learn more about the breakthrough deal “shortly,” officials from Tehran effectively walked away from the negotiating table. The American president with a notoriously short attention span told CNBC, “I really don’t care. I couldn’t care less,” adding that he thought the protracted talks had become “very boring.”....

It led Joe Cirincione, the vice chair of the Center for International Policy and a longtime expert on nuclear policy, to highlight an underappreciated observation: “Trump is perhaps the world’s worst negotiator.”....

But has anyone seen any evidence at all that Trump has had any success as a political dealmaker? The hype is certainly obvious and ubiquitous — I could retire if I had a dollar for every Republican who has referred to the president’s ghostwritten “Art of the Deal” — but proof that bolsters the partisan assumptions is elusive.

As The Atlantic’s David Graham explained last week:

Donald Trump’s reputation and political career were built on his dealmaking prowess, yet the president keeps demonstrating that he is a terrible negotiator.

Repeatedly over the past nine years, Trump has gotten rolled by counterparts during high-stakes exchanges. North Korea, Russia, Russia again, China, and China again have gotten the better of the United States. Trump has had to slink back to Washington without much to show except empty talk about friendship with whatever dictator has just run circles around him. He’s had some success in brokering agreements when acting as a third party (though not nearly as much as he pretends) but much less luck when his own government is a participant.

Unfortunately, the problem isn’t limited to foreign affairs and international diplomacy. As a candidate in 2016, Trump told Fox News, “The problem with Washington, they don’t make deals; it’s all gridlock. And then you have a president that signs executive orders because he can’t get anything done. I’ll get everybody together.”.....

But the evidence of Trump actually succeeding on this front does not exist. There were literally zero instances in which he successfully brought Democratic and Republican leaders together and negotiated a major legislative breakthrough during his first term. Indeed, after a few years in the White House, Trump largely gave up on even trying to make deals with Congress, and in his second term, we’ve seen more of the same.

The Washington Post reported in August 2020, “The president who pitched himself to voters as the consummate negotiator and ultimate dealmaker has repeatedly found his strategies flummoxed by the complexities and pressures of Washington lawmaking.” In a related Post column, Jackson Diehl explained, in reference to Trump, “He’s not up to serious negotiation. He can’t be expected to seriously weigh costs and benefits, or make complex trade-offs. He’s good at bluster, hype and showy gestures, but little else. In short, he may be the worst presidential deal maker in modern history.”

trump is a horrible negotiator and gets bored too quickly to make a deal.