MassGOP blasts Rep. Ayanna Pressley over landlord income

Flint McColgan, Boston Herald on Sep 7, 2025

By clicking submit, I authorize Arcamax and its affiliates to: (1) use, sell, and share my information for marketing purposes, including cross-context behavioral advertising, as described in our Privacy Policy , (2) add to information that I provide with other information like interests inferred from web page views, or data lawfully obtained from data brokers, such as past purchase or location data, or publicly available data, (3) contact me or enable others to contact me by email or other means with offers for different types of goods and services, and (4) retain my information while I am engaging with marketing messages that I receive and for a reasonable amount of time thereafter. I understand I can opt out at any time through an email that I receive, or by clicking here

Boston U.S. Rep. Ayanna Pressley, famous for camping out on the Capitol steps for taxpayer-funded rent relief, earned a hefty profit as a landlord, according to a New York Post analysis.

The fourth-term congresswoman disclosed as much as $8 million in assets in her 2024 financial disclosure, which includes $350,000 from a property sale and rent checks, a Post analysis of her 2024 financial disclosure found.

The perceived hypocrisy of Pressley’s political statements compared to those sources of her income didn’t sit right to some observers.

“Congresswoman Pressley is continuing the long Democratic Party tradition of enriching herself while purporting to do good,” MassGOP Executive Director John Milligan told the Herald Saturday. “There’s nothing more ironic than a Squad member landlord with luxury property income. Her out-of-touch policies are only matched by her exorbitant income.”

Republican National Committee spokeswoman Kierstan Pels told the Post something similar: “Ayanna Pressley is a hypocrite who preaches socialism while pocketing millions.”

The massive spike in rental income — which includes a spot in Edgartown in Martha’s Vineyard where the Obamas and Martha Stewart have homes — is a far cry from the $15,000 in rental income she and her husband, Conan Harris, reaped in 2020, according to contemporary Herald reporting.

That year, she and others — including fellow “Squad” members Rep. Ilhan Omar, D-Minn., Rep. Alexandria Ocasio-Cortez, D-N.Y., and Rep. Rashida Tlaib, D-Mich — re-introduced the “Rent and Mortgage Cancellation Act.”

The bill would have instituted a “nationwide cancellation of rents and primary home mortgage payments through the duration” of the coronavirus pandemic.”

Pressley described the need for the bill in a tweet: “We must cancel rent, extend eviction and foreclosure moratoriums, provide rental assistance, and offer legal representation for those at risk of eviction.”

But she did not respond to questions at the time on whether she and her husband canceled rent during the pandemic, according to reporting at the time.

Pressley represents the 7th Congressional District, which covers most of Boston, other than downtown and South Boston — which is Congressman Stephen Lynch’s district — and surrounding areas to the immediate north and west of Boston. Before being elected to Congress in 2018 she served on the Boston City Council for eight years.

_____