Michael Calderone is Media Editor at TheWrap, overseeing coverage of the industry, and with an emphasis on the intersection of media and politics. He was most recently an editor at Vanity Fair and has reported on the media for Politico, HuffPost, and The New York Observer. He has also taught journalism courses at Princeton University and New York University.
Experience:
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The Media Front: All the News That’s Fit to Predict
In this edition: CNN, CNBC, Dow Jones, CBS, the Washington Post, the California Post, Politico, Kalshi, Polymarket and more
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Columns
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Washington Post Demands Return of Reporter’s Materials From ‘Outrageous’ FBI Seizure
“Anything less would license future newsroom raids and normalize censorship by search warrant,” the Post says
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CBS Finally Airs Shelved ‘60 Minutes’ ‘Inside CECOT’ Report Despite Trump Admin No-Show | Analysis
CBS News chief Bari Weiss didn’t get Trump officials on camera as desired, but U.S. viewers witnessed the plight of Venezuelan men sent to a hellish El Salvador mega-prison
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Columns
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Inside Media’s Risky Bet on Explosive Prediction Markets | Analysis
Through partnerships with Kalshi and Polymarket, newsrooms are harnessing real-time odds to inform coverage — even as prediction platforms face intensifying scrutiny and fuel dystopian fears
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Journalism
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The FBI’s Search of a Washington Post Reporter’s Home Crosses a Dangerous Line | Analysis
Journalists and First Amendment experts express alarm over the government’s action, which one suggests is “meant to intimidate” the press
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Columns
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ICE Shooting Video, White House Spin, and the World We’re In
The Media Front newsletter aims to cut through the outrage and misleading narratives, and interrogate how power, politics and technology converge to shape the media today
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Journalism
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Tony Dokoupil Charts a Trump-Friendly Course for the ‘CBS Evening News’ | Analysis
From amplifying the White House’s January 6 spin to saluting Marco Rubio, the newly minted anchor is signaling a less adversarial tone out of the gate
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Columns
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After a Rocky Year, Newsrooms Push Deeper Into AI
Editorial missteps, staff resistance and public skepticism haven’t slowed experimentation as news outlets wrestle with how to embrace AI without eroding trust
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Journalism
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Donald Trump Watched Venezuela Strike In Real-Time Like ‘a Television Show’ | Video
In a Fox News interview, Trump recalled witnessing the attack from Mar-a-Lago and dismissed criticism that the strike was “unjustified” and “illegal”
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Donald Trump Says Venezuela’s Leader Has Been Captured in US Strike
The stunning military action follows months of US pressure on Nicolás Maduro’s government
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How Journalists Survived — and Even Thrived — as Trump’s War Against Media Escalated in 2025 | Analysis
Billion-dollar lawsuits and new press restrictions didn’t stop journalists from holding power to account as they navigated an unprecedented tsunami of news this year
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Columns
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Bari Weiss Is Eroding Fragile Trust at CBS News | Analysis
Weiss may be a TV news novice, but she isn’t politically naive. Her mishandling of a “60 Minutes” investigation is, at best, clumsy, and at worst, cover for the Trump administration
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Columns
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CBS News Insider on Bari Weiss’ ‘60 Minutes’ Fumble: ‘Series of Unfortunate Events’ | Exclusive
Behind-the-scenes concerns about a lack of a voice from the Trump administration played out while the piece was already being promoted publicly
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‘60 Minutes’ Abruptly Pulls Segment on Trump Deportees Sent to El Salvador Megaprison
Correspondent Sharyn Alfonsi decries the move as “political,” and warned the broadcast was handing the administration a “kill switch”
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Donald Trump’s CNN Grudge Looms Over Warner Bros. Discovery Deal | Analysis
The president has inserted his desire for a revamped CNN into the center of the Paramount-Neflix battle
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Columns
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