Massachusetts socialist Rep. Ayanna Pressley, who once camped out on the Capitol steps demanding taxpayer-funded rent relief, owns a million dollar mansion in Martha’s Vineyard and has seen her net worth balloon to millions since joining Congress, recent financial disclosures reveal.
Now, Pressley and her husband, convicted felon Conan Harris, are facing calls for them to give up their property they said was on land stolen from American Indians.
The two raked in up to $350,000 from a property sale and rental income last year, including from their property in Edgartown on Martha’s Vineyard, according to her 2024 annual financial disclosure. The far-Left Democrat congresswoman disclosed as much as $8 million in assets, making her a millionaire for the first time and joining fellow “Squad” member Rep. Ilhan Omar in the millionaire’s club.
“Ayanna Pressley is a hypocrite who preaches socialism while pocketing millions,” Republican National Committee spokeswoman Kiersten Pels told the New York Post.
The windfall represents a massive jump from the $15,000 Pressley declared in rental income back in 2020, when she owned just one property—the couple’s gated home in the Hyde Park neighborhood of Boston that they converted into a multi-family building.
Pressley’s real estate fortune comes despite her long history of attacking landlords, demanding rent cancellation, and claims that all Americans live on “stolen land.”
In 2020, Pressley joined fellow Squad members Omar, Alexandria Ocasio-Cortez and Rashida Tlaib in reintroducing the “Rent and Mortgage Cancellation Act,” which would have instituted a nationwide cancellation of rents and primary home mortgage payments during the coronavirus pandemic.
“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,” Pressley wrote on social media in August 2020.
Pressley should now be described as “Rep. Ayanna Pressley, D-Martha’s Vineyard,” Boston Herald columnist Howie Carr wrote.
“For that is indeed where she and her jailbird husband now own a million-dollar mansion, in Edgartown, according to her latest Congressional financial disclosure statements,” Carr added. “They have also become landlords, a class she always used to demonize.”
“She’s always denouncing the round-ups of violent illegal aliens by federal authorities. Yet I seem to remember that when a horde of these illegals showed up on the island in 2022, they were hustled off the island at gunpoint by the National Guard within 48 hours,” Carr wrote.
Pressley’s husband, Conan Harris, served 10 years in prison for drug trafficking. In January 2019, shortly after Pressley became a member of the U.S. House of Representatives, Harris resigned from his position as a senior public safety adviser at Boston City Hall to form his own consulting firm, Conan Harris & Associates.
When asked about the couple’s Martha’s Vineyard property, Pressley’s camp told the Boston Herald that “conflating (Conan’s) income and property with hers is misleading. Mr. Harris was a long-term government employee and continues to do meaningful work in the community. The Congresswoman is a steadfast champion for economic justice and opportunity for every family. Her record speaks for itself.”
MassGOP Executive Director John Milligan said there is “nothing more ironic than a Squad member landlord with luxury property income.”
“Her out of touch policies are only matched by her exorbitant income,” Milligan said.
Pressley was also recently criticized on social media after posting about so-called Indigenous Peoples’ Day, with critics pointing out she owns property she claims is “all on stolen land.”
“Happy Indigenous People’s Day! We are all on stolen land. And while Republicans try to whitewash American history, we acknowledge our country’s role in inflicting trauma on our Indigenous neighbors,” Pressley wrote on October 13.
“You should consider giving back your stolen land then—starting with your $1.1M house on Martha’s Vineyard,” conservative activist Greg Price responded.
Pressley represents Massachusetts’ 7th Congressional District, which includes the northern three-quarters of Boston, most of Cambridge, and several surrounding communities. She was first elected to Congress in 2018 and is a member of the progressive “Squad.”