Ayanna Pressley’s Millionaire Glow-Up Drips with Hypocrisy – Twitchy

Ilhan Omar isn’t the only ‘Squad’ member getting rich very quickly. Ayanna Pressley has found her very own path to massive wealth.

Squad’s Ayanna Pressley reaps windfall as Boston landlord, joining Omar in millionaire club: ‘hypocrite’ https://t.co/s5V6BE2SEH pic.twitter.com/bOBpUQIbIp

— New York Post (@nypost) September 6, 2025

Lefty Rep. Ayanna Pressley – who once camped out on the Capitol steps for taxpayer-funded rent relief — reaped a windfall as a Boston landlord last year, The Post has learned.

Pressley (D-Mass) and her ex-con hubby, management consultant Conan Harris raked in up to a staggering $350,000 in profit last year from a property sale and rental income that includes a decidedly capitalist pad on Martha’s Vineyard, Pressley’s 2024 annual financial disclosure reveals. 

Financial disclosures show Pressley — who disclosed as much as $8 million in assets, the first time she’s declared over $1 million — now joins Squad comrade Rep. Ilhan Omar (D-Mich.) in the millionaire’s club, a far cry from the working-class warrior image she tries to project.

“Ayanna Pressley is a hypocrite who preaches socialism while pocketing millions,” Republican National Committee spokeswoman Kiersten Pels told The Post.

Wow, she even has real estate on Martha’s Vineyard now! Nice work if you can get it.

Omar, Bernie, AOC, Mamdani, Pressley, Pocahontas: The most progressive politicians in America, who spend all day criticizing millionaires, are ALL millionaires many times over. (they fly private jets, go on luxury trips, have private security, own multiple homes, drive expensive…

— 🇺🇸 Red Pill Czar 🇺🇸 (@RedPillCzar) September 6, 2025

Recommended

pic.twitter.com/Eh8Rj43wfV

— DarkPoolFeline (@PoolFeline) September 6, 2025

Bless their hearts. 

@AyannaPressley

Every day Americans are struggling while Democrats are getting richer by the day.

Forget all the talk about billionaires. The conversation should be about millionaires. Millionaires who make $200,000 per year in Congress.

President Trump, these people need to…

— Mackinaw Patriot 🇺🇸♥️ (@MackinawPatriot) September 6, 2025

They rail on and on about millionaires, yet they belong to that club. 

How does a man who spent 10 years in prison get a job as deputy director of public safety w/city of Boston City then start his own business raking in up to a million dollars? People I know who go to prison for a very short time can barely get a minimum wage job!

— Lori Prockish (@lori_prockish) September 6, 2025

Crazy how that works!

Hahaha. Seems like all the so called socialists are actual millionaires. Her Bernie and Omar are a bunch of frauds.

— HansVon (@hansvon55) September 6, 2025

They were only mad about ‘millionaires’ until they become millionaires themselves. 

Hahaha. Seems like all the so called socialists are actual millionaires. Her Bernie and Omar are a bunch of frauds.

— HansVon (@hansvon55) September 6, 2025

Typical commies. 

That’s it! Since I’m dead broke and work over 40 hours a week, I’ve decided to run for Congress. I need some a slice of the pie!!! pic.twitter.com/k3p5TZMwXd

— HardParm (@HardParm69) September 6, 2025

Seems like the only way to get rich lately. 

Champagne socialists

— Elvis Knevil (@ElvisKnevil) September 6, 2025

That’s the perfect description.

Editor’s Note: The mainstream media continues to deflect, gaslight, spin, and lie about President Trump, his administration, and conservatives.

Help us continue to expose their left-wing bias by reading news you can trust. Join Twitchy VIP and use promo code FIGHT to get 60% off your membership.