Kevin D. Williamson, the national correspondent for The Dispatch (and previously a longtime writer at National Review), has been one of the most prominent conservative critics of Donald Trump since at least 2015, when he authored the book The Case Against Trump. His views on Trump have been consistently negative, portraying him as unfit for office due to character flaws, incompetence, authoritarian tendencies, laziness, and policy inconsistencies (e.g., labeling Trump a "socialist" in economic approach or a "poisonous buffoon").
Areas Where Williamson Has Been Proven Wrong
- Electoral Predictions and Viability:
- In 2016, Williamson was part of the "Never Trump" movement and dismissed Trump's chances of winning the GOP nomination or general election, viewing him as a fringe figure who would flame out. Trump won both, defying Williamson's (and many conservatives') expectations. Williamson later acknowledged this indirectly in writings, noting how Trump's appeal to working-class voters (which he had critiqued harshly in pieces like his 2016 National Review essay on "white ghetto" pathologies) proved politically potent.
- For the 2024 election, Williamson wrote extensively against Trump, calling him a "moral grotesque" who attempted a coup and arguing in October 2024 that neither candidate (Trump or Kamala Harris) was qualified but Trump's deficiencies were far worse. He implied Trump was unelectable among principled conservatives, yet Trump won decisively. In a post-election piece (December 2025), Williamson reflected on this, suggesting the "Trump movement" might already be in "death twitches," but early 2026 indicators (e.g., Trump's policy rollouts like tariffs) show sustained influence, contradicting that optimism.
- Underestimating Trump's Policy Durability and Appeal:
- Williamson has criticized Trump's economic policies as reactive, protectionist, and non-conservative (e.g., tariffs as "socialist" interventions). However, Trump's trade agenda (including 2025 expansions) has resonated with voters and boosted sectors like steel, as seen in recent economic data—areas where Williamson predicted broader failure or backlash. In a 2025 podcast appearance on Free the Economy, he doubled down on perils of populism but admitted neoliberalism's past successes (which Trump opposes) didn't prevent his rise.
- On foreign policy, Williamson warned Trump would weaken U.S. alliances (e.g., against China), but Trump's second term has seen aggressive stances on China via tariffs. Some alliances (e.g., with Europe) have held despite bluster, partially disproving dire predictions of isolationism.
Cmon man, he is an anti Trumper that has been wrong quite a bit on Trump.
According to him, Trump couldn't even win the WH. Whoops!