Summary

• Pressley went from claiming negative net worth to declaring up to $8 million in assets — her first time crossing the millionaire threshold
• She owns a $1.1 million Martha's Vineyard vacation home where the Obamas and Martha Stewart are neighbors
• Her ex-con husband's consulting firm has pulled in up to $1 million per year since she joined Congress in 2019
• The couple collects up to $350,000 annually in rent from multiple Massachusetts properties
• She spent tens of thousands on private security while pushing to defund the police
• Her husband stands to profit from a luxury megadeal on public land that MDN first exposed

She built her brand fighting for the little guy. Now she owns a vacation home where the Obamas summer, collects rent from the working class, and her ex-con husband's consulting firm pulls in up to a million a year. Welcome to the Squad.

Rep. Ayanna Pressley has gone from claiming negative net worth to declaring up to $8 million in assets — the first time she's crossed the million-dollar threshold. Her portfolio includes a $1.1 million Martha's Vineyard vacation home, multiple rental properties across Massachusetts generating up to $350,000 a year, and a stake in a massive luxury development on public land.

Not bad for someone who camped out on the Capitol steps demanding taxpayer-funded rent relief.

The Consulting Goldmine

Pressley's husband, Conan Harris, spent a decade in federal prison on drug trafficking charges. After his release, he worked his way into Boston's political establishment, eventually landing a job as deputy director of public safety at Boston City Hall.

Then came 2019 — the year Pressley was sworn into Congress as a freshman lawmaker. That same year, Harris left City Hall and founded Conan Harris & Associates, a management consulting firm.

The timing was remarkable. So was the money.

By 2021, the firm was pulling in upwards of $300,000 annually. By 2024, Pressley's financial disclosure showed the firm generating between $100,000 and $1,000,000 in income.

Who are Harris's clients? The disclosure doesn't say. But his wife votes on federal policy affecting every industry in America.

From Prison to Penthouses

The real estate portfolio tells its own story.

In 2020, Pressley declared just $15,000 in rental income from a single property — the couple's gated Hyde Park home, converted to a multi-family building.

Four years later? The Pressley-Harris household owns:

• A $1.1 million vacation home in Edgartown on Martha's Vineyard — neighbors include the Obamas and Martha Stewart
• A two-unit rental property in Mattapan that generated $50,000-$100,000 in rent last year
• Multiple additional rental properties across Massachusetts
• A Fort Lauderdale condo they flipped for a quick $67,000 profit after owning it just over a year

Total declared assets: up to $8 million. Total rental income last year: up to $350,000.

The BWSC Megadeal

But the biggest payday may still be coming.

Mass Daily News first reported that Conan Harris is listed as a Partner & Investor in DREAM Development — the firm selected by Boston's planning agency to co-develop a 400-unit luxury megaproject on former Boston Water & Sewer Commission parking lots.

The project is worth hundreds of millions of dollars. As a Partner & Investor, Harris shares in the upside.

Mayor Michelle Wu praised the deal as "public land for public good." Critics see it differently.

"They basically step by step crammed this down the community who opposes it," one insider told Mass Daily News. "And the BPDA and Zoning Board rubber stamp it without addressing community concerns. Probably due to who the developer is."

The project is advancing through Boston's approval process. When complete, the Pressley household stands to profit from luxury housing built on land that once belonged to the public.

Defund the Police, Fund My Security

Pressley's policy positions make the wealth even harder to square.

She's been a vocal supporter of the "defund the police" movement. She once demanded that health workers — not cops — handle 911 calls and crime scenes.

Meanwhile, she's spent tens of thousands of dollars on private security — paid for by campaign funds.

The message: police protection for me, social workers for thee.

The Pattern

Pressley isn't the only Squad member whose finances have raised eyebrows.

Rep. Ilhan Omar (D-Minn.) recently declared between $6 million and $30 million in assets — despite previously denying she was a millionaire.

Rep. Alexandria Ocasio-Cortez, who famously claimed she couldn't afford a Washington apartment before her first paycheck, now owns property and has built a substantial portfolio.

The pattern is consistent: preach class warfare, practice capitalism.

The Bottom Line

Ayanna Pressley went from negative net worth to an $8 million real estate empire in the span of a few congressional terms.

Her husband went from federal prison to a consulting firm that generates up to $1 million a year — founded the same year his wife joined Congress.

The couple owns a Martha's Vineyard vacation home, collects rent from multiple properties, and stands to profit from a luxury megadeal on public land.

And she's still out there railing against landlords and wealth inequality.

The numbers don't lie.