Thomas O’Brien, real estate developer and CEO of HYM Investment group, will announce his bid to unseat Boston Mayor Michelle Wu next week, according to multiple news reports.
O’Brien, 61, joins a growing pool that, so far, includes the former CEO of the Boston chapter of the Boys & Girls Club Josh Kraft, and local activist Domingos DaRosa.
His announcement comes as Mayor Wu rides a wave of national attention garnered after delivering a defensive testimony on Boston’s sanctuary city policies before a congressional panel and a similarly defensive State of the City address. Wu is scheduled to officially kickoff her re-election bid next month.
Even though incumbent mayors have historically enjoyed easy re-elections in Boston, Wu’s first fight to hold the seat represents a new test to that assumption as the city’s first non-white and first woman elected mayor.
O’Brien may represent an arguably more formidable challenge to Wu than the other declared opponents since his livelihood is tied to an industry that the mayor has publicly struggled against in recent months. His work is also seen by some as directly impacting one of Boston’s biggest problems – housing affordability.
The company he runs is currently leading a 10,000-unit Suffolk Downs housing development in the East Boston-Revere area, and a multi-use development in Nubian Square set to feature affordable housing, a life sciences training center and a new museum.
He is, according to the Boston Globe, already polling on issues like residential property taxes and Boston Public Schools – two major issues the mayor will have to address as the campaign season gets underway.
Wu tried multiple times to spare residents a property tax hike by increasing the city levy on commercial properties for three years. After quarreling, then compromising with prominent leaders in the commercial real estate industry, her legislation was blocked from formal consideration by a South Boston state senator who racked up thousands of dollars from real estate-related entities in the final months of 2024.
Now, despite having no previous experience holding elected office, O’Brien is poised to capture support from a key constituency that usually aligns with incumbents in hopes of securing a favorable rapport with power.
O’Brien is also a former director of the Boston Redevelopment Authority – and worked under Mayor Thomas Menino to help devise South Boston’s luxury neighborhood, the Seaport – an experience that may hurt him with long-time residents who deeply disliked how that agency operated .
All mayoral candidates will face each other in a September primary election. From there, the top two will advance to a campaign sprint until the November general election.
