Analysis: For Trump, results have often revealed the art of no deal

Read the original at Toronto Star ↗
Cite

Weissert, W. (2026, October 18). Analysis: For Trump, results have often revealed the art of no deal. Toronto Star. https://www.thestar.com/news/analysis-for-trump-results-have-often-revealed-the-art-of-no-deal/article_2acc0483-2a53-57c8-ba61-77bf46b1b238.html

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Toronto Star · collected 2026-10-18 · by Will Weissert

Quick Summary

An analysis from the Associated Press examines former President Donald Trump's reputation as a master dealmaker, highlighting discrepancies between his boasts and actual achievements both in office and in his private business career. The piece points out failed negotiations such as those with Iran and Russia, where promises of successful outcomes did not materialize. In the corporate world, Trump often exaggerated success while underpaying or withholding payments from contractors who worked for him. Overall, critics argue that Trump's dealmaking prowess is overstated, noting mixed results and overpromising.
Written locally by qwen2.5:14b on 2026-10-18, using this article's own text rather than the other coverage of the same event (that is the story summary below).

AI analysis runs on qwen2.5:14b, locally

Story summary

Summary unavailable.

Written for “Trump's Deal Results Analysis” on 2026-10-18, grounded in this article and the 0 other(s) covering the same event.
Why this leaning score
The model judged this article politically coded and scored it -0.65, but 2 quote(s) could not be found in the article and the other 2 are attributed speech rather than the article's own narration, so the score is not published.
Written under an earlier scoring contract, which gave a paragraph rather than checkable quotes. Re-analysing this article replaces it.
Leaning score withheld for article 88809: no verified evidence · logged 2026-10-18

Story

📰 Trump's Deal Results Analysis
Politics · 1 article(s) covering the same event.

Compared with similar articles

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How this article was measured signals, leaning charts, publisher record, byline, topics and claims

Signals How these are calculated →

Claims extracted
73
sentences that state something as happening or true
Uncertain
14%
10 of 73 hedged ("reportedly", "may", "according to")
Leaning
withheld
no quote in the article backed the model's score
Publisher signals
63/100
Toronto Star's corrections and hedging, across everything collected from it. Not a measure of accuracy.
Outlets on this story
1
Politics
Same framing elsewhere
1
articles that frame the event the way this one does
Analyzed 2026-10-18 · how these are computed

How this is being covered How these are calculated →

Article leaning vs. publisher reliability
Source leaning vs. consistency

Publisher

Toronto Star · 8033 article(s) · 22 correction(s) detected
Running correction rate · 22 correction(s)
2026-10-07
Correction
2026-09-24
Correction

Who wrote this

Will Weissert
15 article(s) here · 1 carrying a prediction
🔮 WASHINGTON (AP) — Trump Tower had just opened and “The Art of the Deal” three years from publication when 38-year-old Donald Trump suggested he could negotiate Russian arms control better than Ronald Reagan.
🔮 Democratic Virginia Rep. Don Beyer noted on social media shortly after the announcement of the sanctions being suspended that he and others had “warned” Trump might make such a move.
🔮 Trump said Russia will immediately supply more than 300,000 tons of diesel, followed by an additional 500,000 tons in November and 1 million tons “immediately thereafter”.
🔮 The visits come as the Republican president works to bolster his party in Nov. 3 elections that will determine control of Congress, and they follow stops earlier this week in Ohio and Alaska.
🔮 WASHINGTON (AP) — The midterm elections might look ominous for President Donald Trump, but there are places where his Republican Party could turn the tables on Democrats if it can peel off a few key wins in key congressional races.
🔮 SAN ANTONIO (AP) — President Donald Trump announced Wednesday night that he would award the Presidential Medal of Freedom to fireballer Roger Clemens, calling the seven-time Cy Young winner “maybe the greatest pitcher of all time.”
🔮 It’d be awfully hard,” Trump said Wednesday, when asked if Hurricane Isaias — and a forecast track which has parts of Alabama, Mississippi and Florida bracing for significant impacts — might alter his plans.
🔮 WASHINGTON (AP) — President Donald Trump said Monday that he will stop using taxpayer funds for television advertisements glorifying himself that sparked a major backlash, and instead tap his super PAC to cover costs going forward.
🔮 When asked by Time magazine last week what he would miss most about the White House after he leaves, Trump said, “This beautiful room that nobody should be allowed to rip down.
🔮 When asked by Time magazine last week what he would miss most about the White House after he leaves, Trump said, “This beautiful room that nobody should be allowed to rip down.
Also by Will Weissert
Trump puts new Russia sanctions passed by Congress on hold
2026-10-17 · The Sydney Morning Herald
Nothing else under this byline is closely related to this article, so these are simply their most recent.
All 15 articles by Will Weissert →

Topics

New York Republican Russian The Washington Post WASHINGTON

Subjects

Trump PERSON · 14× Alaska GPE · 1× Donald Trump PERSON · 1× Florida GPE · 1× New York GPE · 1× Republican NORP · 1× Ronald Reagan PERSON · 1× Russian NORP · 1× The Washington Post ORG · 1× WASHINGTON GPE · 1×

Narrative

That image of wealth and success helped launch his first presidential run “because people feel like, ‘Well, if he’s the president some of that success and wealth is gonna rub off on me,’” said Joel Penney, a professor at Montclair State University who studies the intersection of pop culture and politics.
framing: assertive · carried by 1 article(s) · first seen 2026-10-18
🔮 WASHINGTON (AP) — Trump Tower had just opened and “The Art of the Deal” three years from publication when 38-year-old Donald Trump suggested he could negotiate Russian arms control better than Ronald Reagan.
2026-10-18 · Toronto Star
Analysis: For Trump, results have often revealed the art of no deal · assertive framing

Claims (73 extracted, 10 hedged)

WASHINGTON (AP) — Trump Tower had just opened and “The Art of the Deal” three years from publication when 38-year-old Donald Trump suggested he could negotiate Russian arms control better than Ronald Reagan. uncertain
he → open → Reagan
“It would take an hour-and-a-half to learn everything there is to learn about missiles,” Trump told The Washington Post in 1984. asserted
Trump → take → 1984
“You either have it, or you don’t,” he said. asserted
he → have → it
Before there was much talk of being a personal brand, Trump had landed on his: the consummate, swashbuckling, never-lose negotiator. asserted
Trump → be → his
It was an image he cultivated in the New York tabloids and later on reality TV, repeating it so often that, to his supporters, perception became reality. asserted
perception → cultivate → supporters
Now, as he zigzags the country for Republican candidates, from Florida to Alaska, Trump is exhorting voters to again embrace him as an unqualified success in a midterm election that has become a referendum on his presidency and his record as a dealmaker. asserted
that → zigzag → dealmaker
An examination of Trump’s dealmaking, both in his time in the White House and in the private sector, shows decidedly mixed results. asserted
examination → show → results
“He’s not as good at this as he thinks he is,” said Christopher Preble, senior fellow and director of the Reimagining U.S. Grand Strategy program at the Stimson Center, an international security think tank. asserted
Preble → ’ → Center
As president, Trump’s boasts of deals have not materialized He insisted that Iran would be defeated in mere weeks. asserted
Iran → materialize → weeks
He later brokered what he called a “great” ceasefire, though it quickly fizzled. asserted
it → broker → what
Trump repeatedly has said Tehran is desperate to make a deal to end fighting. asserted
Tehran → say → fighting
That also proved untrue. asserted
That → prove → ?
He promised to negotiate an end to Russia’s war in Ukraine in a day. asserted
He → promise → day
He announced an agreement that he said meant Moscow and Kyiv would not attack each other’s energy infrastructure. asserted
Moscow → announce → infrastructure
That pause never happened, even as the president insisted it would hold. asserted
it → happen → ?
“I said, ‘You agreed,’” Trump said in defending his assertions. asserted
Trump → say → assertions
“That’s why.” asserted
That → ’ → ?
Trump promised he would use the threat of tariffs to negotiate the best trade deals ever, only to offer unilateral duties nearly the whole world over. asserted
he → promise → duties
Those import taxes have raised domestic prices and sparked trade wars with America’s close friends, including Canada. asserted
taxes → raise → Canada
The levies brought in more than $83 billion this year through September, much of it paid for by American consumers and still far less federal revenue than Trump suggested. uncertain
Trump → bring → consumers
Even on less consequential matters, Trump’s deals have foundered. asserted
deals → founder → matters
He said he had a “guy who’s unbelievable at doing swimming pools” who could fix the Lincoln Memorial’s Reflecting Pool for a little more than $1 million. uncertain
who → say → million
Trump’s presidential efforts follow his business patterns The president’s public acts typically mirror a well-traveled private sector pattern. asserted
acts → follow → pattern
He frequently boasted about doing better in negotiations than he really had, then sought to cover expensive missteps by refusing to pay people working for him, often suing them. asserted
he → boast → them
His biggest successes came when he had maximum leverage. asserted
he → come → leverage
“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,’” Preble said. asserted
Preble → spin → much
“There’s a certain bit of tap dancing around those details that he just can’t do given what’s happening in the world today. asserted
what → ’ → world
Trump’s core narrative as master dealmaker had begun to fade until “The Apprentice” debuted in 2004. asserted
Apprentice → begin → 2004
Allowed to play a rich and powerful tycoon on television, Trump rebooted his dealmaker persona. asserted
Trump → allow → persona
That image of wealth and success helped launch his first presidential run “because people feel like, ‘Well, if he’s the president some of that success and wealth is gonna rub off on me,’” said Joel Penney, a professor at Montclair State University who studies the intersection of pop culture and politics. asserted
who → help → culture
But even now, as his approval ratings have sunk to near-historic lows, Trump still insists he is among the best dealmakers the world has known. asserted
world → sink → dealmakers
Tim O’Brien, author of “TrumpNation: The Art of Being The Donald,” said Trump may finally find out after Election Day on Nov. 3 “how much voters believe that he’s a competent manager and a great dealmaker.” uncertain
he → say → Nov.
Many of Trump’s business and presidential deals collapsed Marty Latz, a negotiation expert and author of “The Real Trump Deal: An Eye-opening Look At How He Really Negotiates,” said Trump the businessman saw every negotiation as a zero-sum game. asserted
Trump → collapse → game
“The reality is, he did negotiate some excellent deals, but also that he did fail spectacularly in a number of deals, and that he has never really successfully negotiated as president in a significant number of contexts,” Latz said. asserted
Latz → negotiate → contexts
Trump has long been guided by the notion that he can only win. asserted
he → guide → notion
“He could be a better negotiator if his ego didn’t get in the way,” said Barbara Res, a former executive vice president in charge of construction at the Trump Organization, who wrote “Tower of Lies: What My Eighteen Years of Working with Donald Trump Reveals about Him.” uncertain
Years → get → Him
“Any concession that should be made, he can’t make. asserted
he → make → concession
Then, with the other parts of it, nothing can continue. asserted
nothing → continue → it
He just has to win everything.” asserted
He → have → everything
Some Trump deals have succeeded or still might Top officials in the Trump administration go to great lengths to amplify the idea that he is a master negotiator. “I make one of those deals every day that no normal person would make,” the president said in May, defending having the U.S. take a stake in the Union Pacific-Norfolk Southern rail merger. uncertain
U.S. → succeed → merger
…and 33 more, not listed.
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