Squad’s Ayanna Pressley lives like an elite while selling struggle to Boston

Saturday, September 6, 2025
4 min read
MDN Staff
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Squad’s Ayanna Pressley lives like an elite while selling struggle to Boston

Ayanna Pressley exposed as $8M landlord aristocrat in New York Post bombshell

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BOSTON — Ayanna Pressley has perfected the image of the fiery progressive crusader. But her financial disclosures — first reported by the New York Post — tell a different story: the congresswoman now sits on assets that could soar as high as $8 million, with profits rolling in from property deals and real estate holdings stretching from Mattapan to Martha’s Vineyard.

Pressley, who preaches about taxing the wealthy and rails against landlords, reported up to $350,000 in real estate profits last year alone. A Florida condo sale padded her bottom line, while her Massachusetts portfolio cements her as part of the very class she claims to battle.

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Ayanna Pressley, once the self-styled voice of the working class, now sits atop a fortune that could reach $8 million — with holdings stretching from Mattapan to Martha’s Vineyard.
Ayanna Pressley, once the self-styled voice of the working class, now sits atop a fortune that could reach $8 million — with holdings stretching from Mattapan to Martha’s Vineyard.

Far from the working-class champion she markets to voters, Pressley increasingly resembles a modern-day aristocrat — insulated, flush with wealth, and untouchable at the ballot box. For years, she has coasted through re-elections without a serious challenger, a political dynasty propped up more by branding than results.

Her district, meanwhile, faces sky-high rents, rising crime, and crumbling schools. Yet the congresswoman’s answer has been little more than slogans and hearings, even as her own fortune grows.

The contrast is glaring: a politician who built her brand on class warfare now enjoys the spoils of the very system she condemns — a radical in rhetoric, but in reality, a landlord-millionaire with the comfort of privilege and power.

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