Trump’s dealmaking record scrutinised as he campaigns for midterms

Experts say Trump’s self‑portrayal as a master negotiator clashes with mixed outcomes from his presidency and business deals.

By Felo News Desk · Published Sun, 18 Oct 2026 18:03:57 GMT

What happened

Donald Trump is touring the country urging voters to back Republican candidates while promoting his reputation as a dealmaker, according to two outlets.

What the reports add

The Winnipeg Free Press notes that Trump first boasted in 1984 that he could negotiate Russian arms control better than Ronald Reagan, telling the Washington Post, “It would take an hour-and-a-half to learn everything there is to learn about missiles.”
Fortune reports that Trump’s trade tariffs have generated more than $83 billion in revenue through September, a figure paid largely by American consumers and far below the president’s own estimates.
Both pieces cite Christopher Preble, senior fellow and director of the Reimagining U.S. Grand Strategy program at the Stimson Center, who says Trump “is not as good at this as he thinks he is.”
Fortune adds that Trump’s approval ratings have sunk to near‑historic lows, a detail absent from the Winnipeg story.
The Winnipeg Free Press includes a quote from Montclair State University professor Joel Penney about how Trump’s “Apprentice” persona helped launch his first presidential run.
Fortune includes author Tim O’Brien’s warning that Trump may discover “how much voters believe that” after the November 3 election.

What was said

“You either have it, or you don’t,” Trump said in 1984, describing his dealmaking confidence.
— quoted in both outlets

“He’s not as good at this as he thinks he is.”
— Christopher Preble, senior fellow, Stimson Center, cited by both outlets

“I said, ‘You agreed,’”
— Donald Trump, defending his claim of a pause in Russian‑Ukrainian energy attacks, cited in both articles

“You can spin a real estate deal, as, ’Oh, you know, I got the better part of the deal because I bought it for this much and I sold it for this much,’”
— Christopher Preble, explaining Trump’s negotiation style, both outlets

“Because people feel like, ‘Well, if he’s the president some of that success and wealth is gonna rub off on me,’”
— Joel Penney, professor, Montclair State University, both outlets

“Trump may finally find out after Election Day on Nov. 3 how much voters believe that.”
— Tim O’Brien, author of *TrumpNation: The Art of Being The Donald*, Fortune

How it came about

Trump’s self‑styled dealmaker image began with the 1987 release of *The Art of the Deal* and was reinforced by his reality‑TV role on *The Apprentice* in 2004. The narrative has been revived during his current cross‑country tour, which spans from Florida to Alaska, framing the 2026 midterm elections as a referendum on his record of negotiations in both the White House and his business empire.

Key facts

Donald Trump claims he can negotiate better than past presidents, a claim first made in 1984. (winnipegfreepress.com)
Christopher Preble of the Stimson Center says Trump is not as good at negotiating as he believes. (winnipegfreepress.com)
Trump’s promises on Iran, a cease‑fire, and ending the Ukraine war have not materialised. (fortune.com)