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TGIF: Free Rosie
President Donald Trump speaks in the Oval Office at the White House on September 2, 2025, in Washington, D.C. (Alex Wong via Getty Images)
The White House aims at Rosie O’Donnell. Everything counts as a tip when tips aren’t taxed. Tucker tries out a new 9/11-truth vibe. Check on the Democrats in your life. And much more.
By Nellie Bowles
09.05.25 — TGIF
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I’m writing to you on just another normal, quiet day. Nothing of note. Just my typical complaints, shouted from a mountaintop via bullhorn, that I am being canceled, and also silenced.

And one quick announcement. I know this is the one you’ve been waiting for. It’s true: We’re getting into the institutional subscription game. If you’d like to bring your company, school, or library full access to The Free Press, please send us a note here: Partnerships@TheFP.com.

→ Everything’s a tip now: It’s nice to begin with new scam ideas. The Trump Treasury Department has released a list of 68 jobs that could qualify for the new $25,000 “no tax on tips” deductions. Among them: digital content creators, home plumbers, recreational pilots, and private event planners. I really think the tips exception should be limited to strippers, since if the tip is attached to a thong and covered in sweat, you earned it. No need to march that duffel to your accountant. Otherwise, people should pay normal taxes (but those taxes should all be lower!), especially if you’re a recreational pilot because God knows you got that money from some freak in LA who wants you to take him to Vegas in a propeller plane. Recreational pilots do not need special tax breaks, but the truth is every single recreational pilot is a Trump voter (and oddly, also a TGIF reader), so a tax break they shall have.

Right now our whole tax code is designed to burden full-time wage earners. Like, if you have a job at a company, you’re a fool, I’m sorry to break it to you. Your tax burden is brutal. You can’t even write off the lease on your car? That you use to get to work in? And cry in the parking lot behind the wheel of? What kind of life is that? As Matt Zeitlen of the very smart eco-warrior site Heatmap News put it: “W-2 earners who rent and don’t have kids are holding up the entire sky.” It should not be thus! But thus it is. Our tax system is built to brutalize these people and make them work just a bit more (like, please check Slack on Sundays, Sean, the stability of the nation depends on it). Then the money collected as tax dollars is quickly funneled away. Also, read the great econ writer Noah Smith on why we are “the richest third-world country.”

But personally, I like “no tax on tips” expansion pack. See, I’m a digital content creator, baby. You don’t know this, but every $10 monthly subscription is delivered to me as cash, tucked into my extremely practical briefs.

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Nellie Bowles
Nellie Bowles is a co-founder for The Free Press and its head of strategy. She was previously a reporter at The New York Times, where she won the Gerald Loeb Award for investigative journalism and the Robert F. Kennedy Journalism Award. She started her career at her hometown paper, the San Francisco Chronicle.
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