Josh Kraft, son of the billionaire New England Patriots owner and head of the family’s philanthropic arm, is planning to announce a run for mayor of Boston, according to two sources close to Kraft,

The challenge would set-up a showdown with first-term Mayor Michelle Wu for this year’s election.

Kraft, president of the New England Patriots Foundation, is planning to officially announce his mayoral bid in early February, according to sources with knowledge of the decision, which was first reported by Politico. A spokesperson for Kraft declined to comment.

He is considering office space in Nubian Square as his campaign headquarters, although no decision has been made yet on a location, one of the people who has spoken with him said. He is connected to Roxbury through his position as board chair of the Urban League of Massachusetts, which is located in that neighborhood.

Kraft, who plans to run as a Democrat, has been considering a challenge to Mayor Michelle Wu for months, regularly appearing at events throughout the city.

As recently as last week, Kraft made an appearance at a Dorchester neighborhood meeting on the subject of bike lanes.

A poll testing how he would fare against the popular progressive mayor, given his father’s connection to President Donald Trump and his past contributions to Republican candidates, circulated this past summer, further enhancing speculation that he would jump into the race.

It was Boston City Councilor Ed Flynn’s decision earlier this month to pass on the mayor’s race, however, that provided more of a path forward for Kraft, albeit a difficult one. An incumbent mayor hasn’t lost in Boston since 1949.

Flynn, the son of former Mayor Ray Flynn, has been a vocal critic of Wu on many of her key priorities this year, including the city’s public-private plan to redevelop White Stadium for a professional women’s soccer team and her push to shift more of the city’s tax burden onto businesses, to provide relief to homeowners.

Those two political battles are among the areas that political observers see as vulnerabilities for the mayor that Kraft could seek to capitalize on during the campaign trail, along with school closures and the city’s affordable housing crisis. Wu gave birth to her third child last week and has said she is planning to run for reelection.

The city, for example, is proceeding this week with demolition at Franklin Park’s White Stadium amid a lawsuit from vocal critics that seeks to stop a project that is already costing taxpayers nearly $100 million, and counting. Wu has also struggled to push through her bid to raise commercial taxes over the objections of a struggling real estate sector.

Not helping Wu’s case on the tax shift front has been her rejection of calls to cut a city budget that grew by 8% this fiscal year. Mayor Thomas Menino proposed budget cuts alongside his push for similar tax relief legislation two decades ago.

Jacquetta Van Zandt, host of the Politics and Prosecco podcast, pointed to ongoing problems at Mass Cass, the longtime epicenter of the city’s opioid crisis, as a major issue that hasn’t been resolved under the Wu administration. She said she sees White Stadium as being among the mayor’s “biggest fumbles,” however, in terms of how Wu has dealt with communities of color during her first term.

“Michelle is a very smart woman and she absolutely ran a dynamic campaign last time, but over the past few years, there’s some kind of disconnect within her administration and communities of color, particularly the Black community,” Van Zandt told the Herald. “It’s more of messaging to the Black community and understanding that we’re not a monolith.

“The issues around White Stadium have been, in my opinion, one of the biggest fumbles,” Van Zandt added.

The issue lies more with the lack of transparency around the White Stadium process, “not necessarily” just that the project is happening, she said, adding that it highlights a larger problem with today’s lack of transparency in the city.

While it’s not new that the Black community has felt unheard by a city administration, past thinking was that having Wu, the first person of color and woman to be elected as mayor of Boston, would “reverse that, and it appears that she’s made it very clear that it’s just continue to continue that way.”

“I think that whomever runs, whether it’s Josh, whether it’s whomever, I think that they are going to have to prove that they are willing to listen, work and collaborate with the Black community,” Van Zandt said, adding that Kraft’s past experience as head of Boys and Girls Clubs of Boston may “play in his favor.”

Kraft spent roughly 30 years with the Boys and Girls Clubs of Boston, and more than a decade as Nicholas president and CEO prior to his full-time committment as president of his family’s philanthropic arm.

He would have to overcome the power of incumbency in a city that hasn’t ousted an incumbent mayor in roughly 75 years, however, which one political observer sees as being insurmountable.

Related Articles

Boston’s plan to plow through with White Stadium demolition draws community blowback

Boston City Council pay hiked to $120,000 as most skip ethics session

Boston City Council to probe home assessment variability amid property tax spikes

Boston City Council OKs $110M housing accelerator fund

Boston Mayor Wu’s 301 new hires: ‘Your Tax Dollars at Work’ database

Wu has $1.7 million in her campaign war chest, according to the Office of Campaign and Political Finance, already has endorsements from several labor unions including the two largest city worker unions, and has regularly touted Boston as the “safest major city in the country,” given its record-low homicide rate.

Kraft, the son of billionaire Patriots owner Robert Kraft, will spend some of his own money in the race, sources told the Herald, representing near unlimited funds. He’s also boosted by name recognition that many first-time candidates lack.

One political observer, Brian Jencunas, sees Wu’s incumbency as being insurmountable, however, and previously told the Herald that he views Kraft’s past connection to Republicans as a vulnerability in Boston, a “Democratic stronghold that becomes more progressive every year.”

“Boston is the safest big city in America and property values continue to skyrocket,” Jencunas said in a prior interview. “This is not the environment where an incumbent Boston mayor loses for the first time since 1949.”

Mayor Michelle Wu (Stuart Cahill/Boston Herald)