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REPORT: Far Left Massachusetts ‘Squad’ Member Ayanna Pressley is a Millionaire Just Like Her Pal Ilhan Omar

by September 7, 2025
September 7, 2025

Rep. Ayanna Pressley/Image: Video screenshot

Last week, it was revealed that far left, anti-capitalist Rep. Ilhan Omar of Minnesota is sitting on millions.

Now it turns out, her fellow ‘Squad’ member Ayanna Pressley of Massachusetts is also a millionaire. Pressley has apparently made her fortune in real estate, which is especially funny because she joined other Democrats in leading a movement against landlords just a few years ago.

According to the report, Pressley also owns a property on Martha’s Vineyard, which should surprise no one. Democrats are obsessed with the Vineyard, for some reason.

From the New York Post:

Squad’s Ayanna Pressley reaps windfall as Boston landlord, joining Omar in millionaire club: ‘hypocrite’

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.

“She tells everyday Americans they must be forced to defund the police and live with sky-high crime in their communities while indulging in private security. Pressley is a fraud – just like the rest of the Squad.”

Here are some tweets from Pressley back in 2020, berating landlords.

America needs us to cancel rent. https://t.co/74EvaooJ05

— Congresswoman Ayanna Pressley (@RepPressley) August 10, 2020

Keeping families housed is a matter of public health.

We must cancel rent, extend eviction and foreclosure moratoriums, provide rental assistance, and offer legal representation for those at risk of eviction. This is a public health emergency.https://t.co/jmHEmfVjVa

— Congresswoman Ayanna Pressley (@RepPressley) December 1, 2020

Isn’t it fascinating how almost all of the so-called Democratic Socialists are extraordinarily wealthy?

The post REPORT: Far Left Massachusetts ‘Squad’ Member Ayanna Pressley is a Millionaire Just Like Her Pal Ilhan Omar appeared first on The Gateway Pundit.

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