Why Do Big City Democrats Keep Electing Socialists?

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May 4, 2026

Kate Andrews, Washington Post opinion journalist who covers politics and public policy, joins to dissect why socialist-leaning mayors win in big cities. Short takes on union roots, tax fights, and whether weak alternatives or voter preferences drive outcomes. Also touches on U.S. moves around the Strait of Hormuz and what royal visits reveal about political theater.

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INSIGHT

Head Taxes Dress Up As Corporate Levies

Head taxes are crafted to appear corporate rather than individual to dodge political pushback.
Katherine Mangu-Ward explains these are technically corporate levies keyed to employee pay, but functionally punish high earners.

INSIGHT

Cities Sell A Package Not Just Tax Rates

Taxes matter on the margin but are rarely the primary reason people choose cities; quality and amenities often outweigh tax differences.
Nick Gillespie recounts personal moves and argues cities charge a premium for what they offer beyond tax rates.

INSIGHT

Resilient Cities Can Normalize Socialism

Even if socialist mayors don't collapse cities, their visibility can normalize socialist policies nationally.
Kate Andrews worries New York surviving a light-touch socialism could make voters think socialism 'isn't so bad.'

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This week, editors Peter Suderman, Katherine Mangu-Ward, and Nick Gillespie are joined by special guest Kate Andrews, opinion journalist for The Washington Post, to discuss how big city governance is playing out in Democratic cities. They examine why candidates with strong ties to organized labor and socialist policy agendas, such as New York Mayor Zohran Mamdani and Seattle Mayor Katie Wilson, keep winning in major cities, even as affordability worsens and residents leave. The panel also considers whether these outcomes reflect voter preferences, weak alternatives, or a broader failure of reform-oriented factions on the left.

Next, the panel turns to Iran, where President Donald Trump has announced "Project Freedom," a plan for the U.S. Navy to escort ships through the Strait of Hormuz amid ongoing tensions and uncertainty over the conflict's trajectory. They discuss the economic stakes, the political fallout, and what the lack of a clear resolution suggests about the long-term direction of U.S. foreign policy. The conversation then shifts to King Charles' visit to the United States and what it reveals about political culture, symbolism, and leadership on both sides of the Atlantic. Finally, a listener asks why voters continue to reward pandering politicians and whether meaningful change is possible within the current electoral system.

0:00—Why big city Democrats keep electing socialists
23:01—The Strait of Hormuz and "Project Freedom"
36:35—Listener question on voter behavior
45:34—King Charles visits the U.S.
53:03—Gillespie's interview with Justice Neil Gorsuch
57:08—Weekly cultural recommendations

Mentioned in the podcast:

"Seattle's Socialist Mayor Laughs at Wealthy Residents Leaving To Escape High Taxes," by J.D. Tuccille
"Project Freedom," by Liz Wolfe
"Justice Neil Gorsuch: 'Aspirations for Power Need To Be Checked'," by Nick Gillespie
"Prison Doesn't Work the Way You Think," by Billy Binion
"Is The Devil Wears Prada 2 the Great Millennial Journalism Movie?" by Peter Suderman

The post Why Do Big City Democrats Keep Electing Socialists? appeared first on Reason.com.