Caitlin Flanagan vs. transgender people

Caitlin Flanagan is an American writer, anti-feminist, and anti-transgender activist.

Background

Caitlin Flanagan was born on November 14, 1961 to Jean (Parker) Flanagan and Thomas Flanagan (1923–2002). Flanagan has one sibling, Ellen Flanagan Klavan, who married anti-trans writer Andrew Klavan. Caitlin Flanagan grew up in a devout Catholic household.

Flanagan’s parent Thomas was a writer and professor who taught at University of California, Berkeley. The family moved to New York after Thomas took a position at Stony Brook University.

Flanagan has written about an attempted sexual assault by a high school classmate that occurred in 1978, which led Flanagan to attempt suicide the following year.

Flanagan attended University of Virginia, earning a bachelor’s degree and a master’s degree.

Before becoming a writer, Flanagan was an English teacher and college counselor at Harvard-Westlake school. Flanagan has written for The Atlantic since 1999 and is a former staff writer for The New Yorker.

In 2006, Susan J. Douglas wrote:

Valerie Lawson, author of Out of the Sky She Came, reportedly the definitive biography of Mary Poppins creator Pamela Travers, found much of her research presented as original reporting in a New Yorker article by Caitlin Flanagan. Flanagan interviewed Lawson for the piece, yet her book was never mentioned. The January/February 2006 Columbia Journalism Review reprinted the entire e-mail exchange between Lawson and New Yorker editors over the borrowing.

Flanagan is married to Rob Hudnut. They have twin children, Patrick and Conor. Flanagan has written about living with breast cancer.

Anti-feminism

Flanagan is known for writing with a “relentless antifeminist determinism,” according to Laurie Abraham at Elle. In a 2004 Atlantic essay titled “How Serfdom Saved the Women’s Movement,” Flanagan wrote, “When a mother works, something is lost.”

In naming Flanagan their “first Douchebag All-Star” in 2010, Andi Zeisler of Bitch Media wrote:

It’s in this spirit that we give a nod today to the lifetime douchechievements of Mrs. Caitlin Flanagan: author, columnist, wife, mother, professional scold, and 24-karat-gold douchebag. Flanagan has been honing her tirelessly contrarian standpoints on motherhood, work, abortion, teen girls, sexuality, adultery, and education in the pages of such august publications as The New Yorker and the Atlantic Monthly for almost a decade, and in that time has churned out dozens of stupendously specious, haughty, and intellectually dishonest (and sometimes plagiarized!) reviews and opinion pieces that offer little more than a window on the author’s self-focused worldview.

No douchebag can get it done all alone, of course, and Flanagan has had plenty of help. Obviously, there’s her nannies, her housekeeper, her “personal organizer,” her gardener, and her other household help. More important, there are the many prominent newspapers, magazines, and journals that have hired her to chum the waters of opinion with her irresistible antifeminist comment bait. After all, when you’re a journal of opinion that’s only got one spot for “women’s issues,” why give it to someone who cares about actual women, rather than one who deals only with straw ones? So give it up for Flanagan.

Anti-transgender activism

Flanagan was a signatory on the 2018 Harper’s Letter signed by a disproportionate number of anti-trans activists.

Flanagan is a frequent guest on Real Time with Bill Maher.

Flanagan is closely linked to Bari Weiss, appearing on a Free Press podcast with Suzy Weiss, holding a position at the “anti-woke” University of Austin, and logrolling for Weiss in The Atlantic. Flanagan was a regular guest on The Femsplainers with Danielle Crittenden and Christina Hoff Sommers.

Praising Irreversible Damage by Abigail Shrier, Flanagan posted in 2020: “I hugely recommend this book to parents of teenage girls. It goes beyond issues of trans identity to the whole landscape of adolescent girlhood in our times. It helps parents make thoughtful decisions with their daughters. It is not anti-trans; it’s pro girls.”

In 2022, Flanagan posted in defense of J.K. Rowling: “An article that tries to damn @jk_rowling with her own quotes. There is nothing hateful. Eventually, she will be proven right, and the high cost she’s paid for sticking to her beliefs will be seen as the choice of a principled person.”

In 2025, Flanagan posted about the Trump Administration’s attacks on “gender ideology,” writing, “It was the co-opting of feminism as an ideology naturally aligned with trans rights that produced this moment. Feminism protects the rights of women and girls.”

References

Serano, Julia (August 19 2015). Op-ed: The Truth About Political Correctness. The Advocate https://www.advocate.com/commentary/2015/08/19/op-ed-truth-about-political-correctness

Serano, Julia (August 18, 2015). That Joke Isn’t Funny Anymore (and it’s not because of “political correctness”). Medium https://juliaserano.medium.com/that-joke-isn-t-funny-anymore-and-it-s-not-because-of-political-correctness-469b92312536

Zeisler, Andi (May 19, 2010). Douchebag Decree: Caitlin Flanagan, our first Douchebag All-Star! Bitch Media https://www.bitchmedia.org/post/douchebag-decree-caitlin-flanagan-our-first-douchebag-all-star [archive]

Calderone, Michael (November 27, 2006). Off the Record. https://observer.com/2006/11/off-the-record-2/

Douglas, Susan J. (September 1, 2006). Plagiarists: Catch Your Own Clue. In These Times https://inthesetimes.com/article/plagiarists-catch-your-own-clue original url http://www.inthesetimes.com/article/2782

Lawrence, Jen (June 2006). Searching for Caitlin Flanagan. Literary Mama https://literarymama.com/articles/departments/2006/06/caitlin-flanagan

Cove. Michelle (April 21, 2006). What’s the deal with Caitlin Flanagan?! Jewish Women’s Archive https://jwa.org/blog/caitlinflanagan

Tucker, Judith Stadtman (April 2006). Like I said: Loving and loathing Caitlin Flanagan. The Mothers Movement Online http://www.mothersmovement.org/features/06/04/flanagan_1.html

McLeary, Paul (March 28, 2006). Jack, George, Don and Caitlin: U.S. News and TNR look at Bush’s “CEO administration,” while others reminisce about Jack Abramoff and dig in to the psychology of writer Caitlin Flanagan. Columbia Journalism Review https://www.cjr.org/behind_the_news/jack_george_don_and_caitlin.php

Hulbert, Ann (April 25, 2006). Mother’s Hypocritical Helper: Why Caitlin Flanagan drives her readers nuts. Slate https://slate.com/human-interest/2006/04/caitlin-flanagan-s-to-hell-with-all-that.html original url http://www.slate.com/id/2140544/

Abraham, Laurie (March 15, 2006). Who’s The Fairest Wife Of All? Modern woman Caitlin Flanagan thinks a mother’s place is in the home. Elle https://www.elle.com/culture/career-politics/a9228/whos-the-fairest-wife-of-all-19440/

Anti-trans coverage

American Enterprise Institute with Christopher J. Scalia, Thomas Chatterton Williams, and Caitlin Flanagan (November 16, 2023). The American Dream Lecture Series: Caitlin Flanagan on the Future of Free Speech. https://www.aei.org/wp-content/uploads/2023/10/231116-The-American-Dream-Lecture-Series-The-Future-of-Free-Speech-transcript.pdf?x91208

Paul, Pamela (February 16, 2023). In defense of J.K. Rowling. New York Times https://www.nytimes.com/2023/02/16/opinion/jk-rowling-transphobia.html

Lipsitz, Raina (January 30, 2012). Who’s Afraid of Caitlin Flanagan? The Atlantic https://www.theatlantic.com/entertainment/archive/2012/01/whos-afraid-of-caitlin-flanagan/252143/

Selected writing by Flanagan

Flanagan, Caitlin (October 7, 2025). Don’t Bet Against Bari Weiss: The new editor in chief of CBS News triumphs over her critics. The Atlantic https://www.theatlantic.com/ideas/archive/2025/10/bari-weiss-success/684480/

Flanagan, Caitlin (August 9, 2018). Why the Left Is So Afraid of Jordan Peterson? The Atlantic https://www.theatlantic.com/ideas/archive/2018/08/why-the-left-is-so-afraid-of-jordan-peterson/567110/

Flanagan, Caitlin (September 2015). That’s Not Funny! Today’s college students can’t seem to take a joke. The Atlantic https://www.theatlantic.com/magazine/archive/2015/09/thats-not-funny/399335/

Flanagan, Caitlin (December 12, 2005). Becoming Mary Poppins: P. L. Travers, Walt Disney, and the making of a myth. The New Yorker https://www.newyorker.com/magazine/2005/12/19/becoming-mary-poppins original url https://www.newyorker.com/fact/content/articles/051219fa_fact1 [archive]

Books

Flanagan, Caitlin (2023). On Thinking for Yourself: Instinct, Education, Dissension. Atlantic Editions, ISBN 978-1638931409

Flanagan, Caitlin (2012). Girl Land. Reagan Arthur Books, ISBN 978-0316065986

Flanagan, Caitlin (2006). To Hell with All That: Loving and Loathing Our Inner Housewife. Little, Brown and Company, ISBN 978-0316736879

Media

Making Sense with Sam Harris and Caitlin Flanagan (August 13, 2019). 165: Journey into Wokeness: A Conversation with Caitlin Flanagan. https://www.samharris.org/podcasts/making-sense-episodes/165-journey-wokeness

FIRE / So to Speak with Nico Perrino, Greg Lukianoff and Caitlin Flanagan (November 23, 2021). So to Speak podcast: Caitlin Flanagan and Greg Lukianoff. https://www.youtube.com/watch?v=X3JPgO3Krco https://www.thefire.org/news/so-speak-podcast-caitlin-flanagan-and-greg-lukianoff

The Free Press with Suzy Weiss and Caitlin Flanagan (August 13, 2024). Dear Caitlin Flanagan and Suzy Weiss: A Free Press Advice Special! https://www.thefp.com/p/dear-caitlin-flanagan-and-suzy-weiss-bf0

The Weekly Dish with Andrew Sullivan and Caitlin Flanagan (March 18, 2022). Transcript: Caitlin Flanagan On Cancer, Abortion, Other Christmas Cheer. https://andrewsullivan.substack.com/p/transcript-caitlin-flanagan-on-cancer