Nellie Bowles of The Free Press punctures pretension left and right

As resident jester at the maverick journalism outlet The Free Press, Nellie Bowles scours the news for the absurd and hypocritical, and then skewers the best of the worst in her column, TGIF.

For instance, when Joe Biden warned in his farewell address that billionaires wield too much power, Ms. Bowles scoffed that he only meant Republican plutocrats. “Me, I’m balanced,” she wrote. “I love all our oligarchs, on both sides. ... I want our political battles to be fought on warring yachts off the coast of Croatia.”

The lampooning, along with her book, “Morning After the Revolution” – which argues that progressive politics and mainstream journalists “went berserk” in the early 2020s – have turned Ms. Bowles into a darling among conservatives and disenchanted Democrats.

“If I had to read just one thing all week to both amuse me and inform me without predictable bias, I’d pick Nellie’s TGIF column – so smart, so funny,” says comedian Bill Maher, who has hosted her on his HBO talk show.

But Ms. Bowles’ political views defy easy categorization. “My personal politics are totally chaotic,” she tells the Monitor. “Best described as strong opinions, loosely held. But that’s why I’m a journalist and now mostly a satirist. If I had good political answers to the conundrums of the day, I’d be off doing that.”

For most of her 36 years, Ms. Bowles was a “happy liberal,” a sixth-generation San Franciscan whose beliefs were as synonymous with the city as fog and cable cars. In fifth grade, she stapled photos of factory farm animals to her backpack to protest the campus cafeteria’s meat dishes.

At her high school, an elite boarding academy near Santa Barbara, she led the gay-straight alliance. With a penchant for steel-toed Doc Martens and rainbow stickers, she was initially the only out-of-the-closet student. As a child, “I completely ignored dolls unless it was to decapitate them,” she says in her book.

Ms. Bowles didn’t intend to be a journalist. Hoping to write popular science books, she majored in psychology and comparative literature at Columbia University. The summer before her senior year, she trekked to Montreal to help with a study of hypnosis as a substitute for pain medicine.

She soon realized, however, that “I was very bad at science research.” Still wanting to write, she cajoled her way into an internship at the San Francisco Chronicle and “On Day 1, I knew this was my career,” she says.

Seven years later, in 2017, she snagged the brass ring, joining the San Francisco bureau of The New York Times to cover tech and culture. But a cup of Goldfish crackers and a sojourn in Seattle helped turn her dream job to disillusionment.

Things began crystallizing in 2020, around the time that protesters transformed six blocks of Seattle into a cop-free zone. Amid conflicting accounts on whether the takeover created Camelot or chaos, Ms. Bowles wanted to report on merchants suing the city for withdrawing police and fire protection from the neighborhood. Several Times colleagues questioned her motives, cautioning that such an article would put her “on the wrong side of history,” she recalls.

“For me,” she says, journalism is about “following your curiosity,” not censoring facts that undermine pet political causes. She went ahead with the story, which ended up on the newspaper’s front page.

Ms. Bowles’ love life also raised hackles. Two years earlier, during a trip to New York, she had rendezvoused over fish-shaped crackers with Bari Weiss, a Times opinion editor and writer, to discuss a news tip. “I fell in love immediately,” Ms. Bowles says. A relationship ensued and blossomed into romance.

Some co-workers were aghast. Although Ms. Weiss leans left on a number of issues, her conservative stances on others made her “a perennial political piñata, with just about everyone taking a whack,” as a magazine put it. Citing bullying by colleagues, Ms. Weiss quit the paper shortly before Ms. Bowles’ Seattle story was published. Ms. Weiss’ resignation letter, which also alleged a betrayal of journalistic standards, went viral. As the uproar unfolded, Ms. Bowles suggested they “get out of Dodge,” telling Ms. Weiss, “There’s this place called California and it’s sunny, it’s beautiful, and people are so nice ... and politics is like the 10th thing they care about.” So the couple moved to Los Angeles, got married, and began plotting their future.

When Ms. Weiss envisioned launching a big media company, Ms. Bowles thought the idea was “delusional,” but nevertheless opened an account for her on Substack, a publishing platform popular with exiled journalists. Debuting in January 2021, it took off swiftly, she says.

Meanwhile, Ms. Bowles went on leave from the Times and began her book, which was “more or less a list of stories I wanted to write for The New York Times, but knew I couldn’t.” The topics included a “Toxic Trends of Whiteness” class, a homeless encampment “run by BMW-driving socialists,” and the hollowness of land acknowledgments. (You’re not giving the land back to Native Americans, she sniffs; it’s more like, “Let’s remember that people were slaughtered here on the soil under this beautiful Craftsman house, and then let’s continue on and have dessert.”)

Less than a year into the project, Ms. Bowles quit the paper and joined her wife’s venture as the flagship columnist. The Free Press has since racked up investors, expanded staff, and branched into podcasts and live events. Boasting over a million subscribers (145,000 are paying), it’s a bright spot in today’s mediasphere.

With TGIF, Ms. Bowles is sort of a modern-day Mort Sahl, a political comedian of the 1950s and ’60s. But instead of walking onstage with a newspaper and riffing on headlines like Mr. Sahl, she walks on a treadmill beneath her shoulder-high computer screen while hunting for material to satirize. She test-drives her “rants” over dinner, and finalizes the roundup each Thursday.

Although most of her foils are progressives, she’s not averse to roasting conservative kahunas, including Elon Musk (“Normally you have to kill people to get that powerful”) and President Donald Trump, whose inauguration meme coins are “like tiny Ponzi schemes; the price goes up as long as people keep buying.”

Ms. Bowles acknowledges missing the in-depth reporting that marked her newspaper career, but with a 2-year-old daughter and infant son, such stories are harder to pull off.

“Once the kids are in school, I’ll go back to feature writing,” she says.

Then again, TGIF typically attracts three times as many eyeballs as her Times articles, she notes. “It’s so much fun.”