Boston’s usually sleepy City Council midterms have taken a rare turn in the last few weeks: Two of Mayor Wu’s senior City Hall staffers have pivoted to the campaign trail, becoming candidates challenging incumbent councillors. Add in a longtime Wu supporter running without opposition for an open City Council seat, and as many as three current or former Wu employees could soon be serving on the 13-member body.

Boston mayors have regularly intervened in local elections, from City Council and the State House to state-wide and congressional races. But the old rules are getting tossed, and this year’s council races could become a referendum on her tenure as mayor.

The senior staffers are Henry Santana, who is currently serving as the director of the Office of Civic Organizing and previously was a staff employee of former Councillor Kenzie Bok, and Enrique Pepen, who heads up the neighborhood services office and worked on former US Rep. Joe Kennedy’s 2020 US Senate campaign.

Santana is running at-large, essentially against incumbent Erin Murphy, who was the fourth place finisher in 2021 and is seen as the weakest at-large incumbent.

Pepen is running in District 5, the Hyde Park, Roslindale, and parts of Mattapan district once represented by Thomas Menino and currently home to Roslindale resident Wu herself, against incumbent Ricardo Arroyo.

The third Wu-connected candidate running for City Council is Sharon Durkan. Her biography is significantly different from the other two Wu candidates. She is not in City Hall, and both her resume and the race she is in bear a lot more resemblance to races that past mayors intervened in. Durkan served as a fundraising consultant for Wu’s campaign committee and managed her inauguration committee.

A look back at races that Marty Walsh and Tom Menino got involved in during their tenures highlights how Wu’s approach appears to differ from her predecessors. In 2011, Menino helped Ayanna Pressley win her at-large re-election campaign and aided John O’Toole in his unsuccessful campaign for the open District 3 seat. Pressley was considered the weakest incumbent that year after finishing 4th in 2009 and Menino wanted to prevent Michael Flaherty, his 2009 mayoral opponent, from getting back on the Council. Frank Baker, who held off O’Toole, had the support of then-state Rep. Marty Walsh, and Walsh was widely seen as a future mayoral contender.

In 2015, Mayor Walsh backed Joseph Ruggerio, who lost to Adrian Madaro in the special election for East Boston’s state representative seat. Ruggerio had worked for Walsh’s 2013 mayoral campaign, and his family, which owns a funeral home in East Boston, were prominent Walsh supporters in that neighborhood. Mayor Walsh again endorsed in a race for an open seat in East Boston in 2017, when he backed Stephen Passacantilli, his aide and the scion of a neighborhood political dynasty who lost to Lydia Edwards for the District 1 City Council seat.

So out of these four examples, only one mayor-backed candidate was a winner.

This year could be different, mainly because Santana and Pepen are running against incumbents. Boston politics are known to be cut-throat, but it’s not typical for mayors to recruit candidates to run against incumbents.

The other difference is that Menino and Walsh backed campaign supporters and local allies with their own neighborhood and city-wide networks. Unlike Menino and Walsh’s candidates, Santana and Pepen are both younger and neither has local leadership experience like chairing a Democratic ward committee or leading one of the city’s powerful civic associations. Their status as senior staffers puts the administration much more directly on the ballot.

What that indicates for the future is up for debate. Do her senior staffers’ political campaigns indicate a political organization that is cannibalizing City Hall to challenge incumbents? Does the mayor have an ambition to stock the Council with allies? Or is this simply the personal choice of a few politically minded Boston residents who happen to be city employees? Whichever hypothesis is true, Mayor Wu and her supporters have a lot on the line this fall.

Gregory Maynard is a political consultant and former Boston resident.