Staff Reports
Boston’s political swamp just got murkier—and it stinks to high heaven. In a city supposedly run by progressive champions of fairness and transparency, Boston Mayor Michelle Wu has handed a multi-million-dollar housing project to none other than the husband of Congresswoman Ayanna Pressley. That’s right—the same Ayanna Pressley who parades around as a working-class hero, speaking out of both sides of her mouth while her family cashes in on massive deals cooked up behind closed doors.
Here’s the dirty truth: Pressley’s husband, Conan Harris, a man with a criminal past involving drug trafficking, is a partner and investor in DREAM Development, the firm awarded a $250 million contract to build 400 affordable housing units on city-owned land. This project was rubber-stamped by city bureaucrats who ignored locals’ protests and pushed the deal through like a hot potato—likely because the developer is connected to influential Democrats. It’s the same tired tale liberals spinning as “progress,” but really it’s just another example of backroom political favors lining their own pockets.
EXCLUSIVE: City of Boston hands Ayanna Pressley’s husband a multimillion dollar contract to build luxury megaproject—set to make a fortunehttps://t.co/81nmfczaVK
— Mass Daily News (@MassDailyNews) September 15, 2025
Meanwhile, the hardworking people of Boston—taxpayers and community members—get sidelined while insiders feast. Harris, once a longtime drug felon, now enjoys the perks of deep political connections, having previously worked in city hall and founded his consulting firm the same year Pressley took office. Add to the mix John Barros, a former Boston economic development chief, also involved in the deal. This isn’t some surprise partnership; it’s a revolving door of cronyism and corruption dressed up as “economic development.”
What’s especially galling is the bold-faced hypocrisy from the left. Pressley paints herself as a fighter for the disenfranchised, yet her family’s financial disclosures tell a different story. Between their luxury properties, including a $1.1 million Martha’s Vineyard home, and rental income pulling in hundreds of thousands, it’s clear the squad leader lives very comfortably—even as she claims to champion the working class. This luxury lifestyle is bankrolled by deals like the one her husband just landed, all while everyday Boston residents continue to suffer under skyrocketing rents and crumbling infrastructure.
Mayor Wu’s enthusiastic praise of this deal as a “public good” is the ultimate insult. For the people stuck in neighborhoods where this project will rise, it feels like a slap in the face. They know this isn’t about community vision; it’s about lining the pockets of the political elite while ignoring real local concerns. This is the same administration that’s cozying up to foreign interests and ignoring the will of the people who actually live in these communities.
If Boston’s leadership thinks Americans are too naive to notice this blatant nepotism and crony capitalism, they are sorely mistaken. These are the same politicians who claim to be “for the people” but prove time and again they’re only for themselves and their allies. When will voters learn that the left’s “progressive” agenda is just code for enriching their friends while leaving the rest of us in the dust? Boston’s deal with Pressley’s husband is just one more reason to say enough is enough.
