Earlier this month, the New York Post revealed that Massachusetts Democratic Rep. Ayanna Pressley has up to $8 million in assets, including a $1.1 million Martha’s Vineyard home.

More questions about "the Squad" member's finances emerged this week following reports that her ex-convict husband was handed a multi-million dollar deal by Boston's left-wing mayor. 

Pressley's husband was previously employed by Boston City Hall

According to Mass Daily News, Mayor Michelle Wu's Boston Planning and Development Agency (BPDA) awarded a contract to DREAM Development, of which Conan Harris is listed as a partner and investor.

The Daily Caller noted that Harris, who married Pressley in 2014, is a former gang member who spent over a decade in prison after being convicted on drug trafficking charges.

The website also pointed out that Harris previously served as deputy director of public safety at Boston City Hall before founding a management consulting firm the same year his wife entered Congress.

Harris is not the only former city employee to be affiliated with DREAM Development, as John Barros is also listed as an investor in the company.

As Barros's LinkedIn profile explains, he previously served as Boston's chief of economic development between 2014 and 2021.

Critics suggest that project greenlit "probably due to who the developer is"

One unnamed source who spoke with Mass Daily News suggested that the project is likely an effort by Wu and her allies to reward political friends.

He or she complained local government officials had "basically step by step crammed this down [on] the community who opposes it."

THIS STINKS....AN INVESTIGATION IS NEEDED....

Boston Mayor Wu Handed Multi-Million Dollar Deal To Ayanna Pressley’s Husband https://t.co/wjDk9Ij903 via @dailycaller

— BREAKING NEWZ Alert (@MustReadNewz) September 15, 2025

"And the BPDA and Zoning Board rubber-stamp it without addressing community concerns. Probably due to who the developer is," the source added.

For her part, Wu issued a statement hailing the plan to transform Boston Water and Sewer Commission (BWSC) Lots parking lots into 402 housing units.

"We look forward to partnering closely with Related Beal and DREAM Development"

"This critical designation moves us forward to turn parking lots into housing that addresses residents' needs," the mayor asserted.

"I'm grateful to our City teams for their cross-departmental collaboration to take stock of all of our City-owned properties and ensuring that our redevelopment efforts truly advance public land for public good," she continued.

"We look forward to partnering closely with Related Beal and DREAM Development to ensure the community's vision for this critical development is realized," Wu went on to add.