Squad's Ayanna Pressley labeled 'hypocrite' as she rakes in $350K from property sales and rental income

WASHINGTON, DC: Rep Ayanna Pressley, the Massachusetts Democrat who once camped out on the Capitol steps demanding taxpayer-funded rent relief, is now cashing in as a landlord.

Pressley and her husband, management consultant Conan Harris, reported as much as $350,000 in profit last year from property sales and rental income, according to her 2024 annual financial disclosure reviewed by the New York Post.

After years of presenting herself as a working-class champion, Pressley is now sitting on as much as $8 million in assets, marking the first time she has declared more than $1 million. That puts her in the millionaire’s club alongside fellow Squad member Rep Ilhan Omar (D-MN).

Republicans wasted no time blasting her image.

“Ayanna Pressley is a hypocrite who preaches socialism while pocketing millions,” RNC 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.”

Ayanna Pressley’s path from $15k in rental income to multimillion-dollar holdings

Ayanna Pressley’s financial rise has been dramatic compared to just a few years ago. In 2020, she disclosed only $15,000 in rental income, all tied to her Hyde Park home in Boston, which she and Harris had converted into a multi-family rental to make extra cash.

By 2024, that side hustle had grown into a real estate portfolio. The couple now owns four Massachusetts rental properties, including a $1.1 million three-bedroom home in Edgartown on Martha’s Vineyard — the same zip code where the Obamas and Martha Stewart own homes.

They also own a two-unit rental property in Mattapan, a predominantly Black, low-income Boston neighborhood that brought in between $50,000 and $100,000 in rent last year, records show.

On top of that, the couple briefly owned a $492,500 condo in Fort Lauderdale. They sold it last year for a $67,000 profit.

This is in addition to Pressley’s $174,000 congressional salary for representing Massachusetts’s 7th District.

Conan Harris expands family wealth beyond Ayanna Pressley’s real estate income

Ayanna Pressley’s income wasn’t limited to real estate. She also reported between $100,000 and $1 million in revenue from her husband’s consulting firm, Conan Harris & Associates.

Harris, 48, spent 10 years in prison for drug trafficking before later serving as deputy director of public safety at Boston City Hall. He launched the firm in 2019, the same year Pressley entered Congress.

The business quickly became lucrative. While last year’s disclosure offered only a broad estimate, earlier filings show Harris was already earning more than $300,000 annually by 2021.

Pressley’s team insists none of this undermines her values.

“The Congresswoman and her husband met later in life and keep their finances separate,” a Pressley spokesperson said. “Like many families, they have navigated significant economic hardship, including medical debt, incarceration, and predatory student debt. The Congresswoman is a steadfast champion for economic justice and opportunity for every family. Her record speaks for itself.”

Ayanna Pressley and Ilhan Omar see fortunes rise

Ayanna Pressley is not the only Squad member growing her wealth.

Omar revealed in her 2024 disclosure that she holds between $6 million and $30 million in financial assets

That revelation came just months after Omar dismissed speculation about her millionaire status as “disinformation.”