NEW YORK — The head of one of the nation’s largest teachers unions is facing a serious leadership challenge — a threat that could make it harder for him to play a decisive role in what’s likely to be New York City’s most heated Democratic mayoral primary in years.

As president of the nearly 200,000-member United Federation of Teachers, Michael Mulgrew has been a player in city politics since 2009. He’s helmed the union comfortably for most of that time, but is now in the midst of what’s arguably the most competitive reelection of his tenure.

The state of play was different in 2021. During that year’s mayoral race, Mulgrew was safely ensconced in his perch and used a super PAC partly funded by the union to shell out nearly $4 million to boost the mayoral campaign of then-Comptroller Scott Stringer.

Whether Mulgrew can weather the storm as head of the UFT this year is an open question though, and where the union lands on supporting a mayor also remains unclear. However it plays out, the UFT’s endorsement could move the needle in the upcoming Democratic primary.

David Bloomfield, an education professor at Brooklyn College and the CUNY Graduate Center, contended that Mulgrew’s reelection prospects aren’t tied to his ability to deliver votes. But he said discontent among members could deter educators from following his lead.

“The resources they bring can have an influence, but I think delivering the teacher vote is more difficult than ever because of rank-and-file dissatisfaction with his leadership,” Bloomfield said in an interview, adding that UFT’s endorsement could help candidates but is “by no means predictive of the outcome.”

The union will be counting the ballots from the end of May to the first week of June. And the timing of the union’s endorsement in the June 24 mayoral primary could depend on whether Mulgrew is reelected.

The Democratic primary for mayor is also expected to be hard fought.

The incumbent, Mayor Eric Adams, is facing federal corruption charges, sagging poll numbers and the dilemma of having to explain to voters his growing rapport with President Donald Trump, whose Department of Justice recently dropped corruption charges against him. Former Gov. Andrew Cuomo, who is dominating early polls and was the locus of several high-profile scandals during his tenure in Albany, appears poised to enter the race this weekend. And five other serious declared candidates — including Stringer and the current comptroller, Brad Lander — are also vying for the job.

City Council Speaker Adrienne Adams, who is not related to the mayor, is weighing a bid as well.

The city’s most powerful unions will play a role in the final outcome. Exactly what it will be is still taking shape.

The Hotel and Gaming Trades Council is, for the time being at least, in Adams’ corner. The New York City District Council of Carpenters appears poised to endorse Cuomo. 1199 SEIU, the nation’s largest health care union, has not yet announced its endorsement. And 32BJ SEIU and District Council 37 — both of which endorsed Eric Adams in 2021 — are privately encouraging Adrienne Adams to run for mayor.

“If there’s a candidate that appeals to education or appeals to his members … he may weigh in on the mayor’s race even though his race isn’t over,” someone familiar with Mulgrew’s thinking, who requested anonymity to discuss a sensitive matter, told POLITICO.

Who the UFT ends up backing is also an unknown — as is Mulgrew’s future as its head.

He lost support from retired teachers upset about his role in the city’s push to move them onto a privatized Medicare Advantage plan and has alienated working teachers angry over new curricula and what they view as inadequate pay raises.

Those issues are also at the root of educators’ frustrations with Adams.

“They haven’t been huge fans of the way that Adams has run the school system,” said Peter Allen-Lamphere, a member of the Movement of Rank and File Educators, an opposition caucus. “Usually they back the incumbent because the incumbent is likely to win and their main political orientation is backing the winner. … It’s not clear at all that Adams is the favorite in this race.”

Allen-Lamphere also pointed out that the union’s ability to mobilize its membership in general has been steadily declining for years.

Tough reelection race ahead

Mulgrew’s Unity caucus has controlled the union since the 1960s. Since Mulgrew was elected to his first full term in 2010, he has won the majority of the vote.

Rank-and-file groups have attempted to wrest power from UFT leadership throughout the union’s 65-year history, but have had limited success. They have won some divisions — groups that represent different schools by grade level — but none have succeeded in ousting an incumbent president.

In 2022, a shift in attitude toward union leadership started to take shape when Mulgrew won reelection by his smallest margin yet. Opposition caucuses teamed up, frustrated over his approach to pandemic-era school policies and his push for Medicare Advantage.

Tensions peaked in June when dissident retired teachers ousted his caucus in the Retired Teachers chapter election. The union caps retiree votes at 23,500 in the union election, but it’s usually a reliable voting bloc for Mulgrew.

“Everybody saw the results of the last election,” Jonathan Halabi, assistant secretary for the Retired Teachers chapter, said. “Everybody knows that the retirees shifting really would change how elections happen, and everybody is nervous or excited because nobody knows if that’s a permanent change, a one-time change [or] a gradual change.”

Since then, Mulgrew withdrew his support for Medicare Advantage and advocated for changes to the city’s math and reading curricula. He’s now seeking to bypass collective bargaining to boost the pay of teacher aides who support students with disabilities.

The opposition movement has begun to take shape too. Olivia Swisher, a Brooklyn chapter leader, and Amy Arundell — a former borough official the union reassigned after she allegedly criticized a resolution against Hamas’ attacks in Israel — are challenging Mulgrew on separate slates.

It’s part of a growing movement aimed at ousting veteran union officials. George Gresham, the longtime leader of 1199SEIU, is facing an unprecedented challenge to his leadership as well.

“It makes sense to me that nationally, there are a lot of rank and filers who are throwing their hat in the race and trying to unseat these longtime powerholders,” Swisher said. “These longtime powerholders are very disconnected from the real working conditions of a rank and file member.”

But any effort to topple Mulgrew will likely be an uphill battle. He remains influential among legislators, many of whom are aligned with the teachers union.

In 2022, state lawmakers attached a class size-reduction mandate to a deal to let Adams retain control of the school system, in a win for Mulgrew, for whom the statute is a key priority. Two years later, he secured firmer commitments to ensure the city complies with the statute.

Recently, he convinced some city lawmakers to get on board with efforts to circumvent collective bargaining to give paraprofessionals a pay bump.

“He will have a fight, but I believe that most people in the UFT support the Unity caucus and support Mulgrew because they’ve seen his proven record of results,” said former City Council education chair Danny Dromm, who previously served on the Retired Teachers chapter’s executive board.

LeRoy Barr, UFT’s secretary and Unity’s chair, acknowledged frustrations among members. But he insisted members are sometimes unaware of the caucus’ track record, pointing to achievements such as pay raises in the most recent contract and improved pension benefits.

Their strategy rests on putting in the work to highlight that record, he said.

“We are listening to the members,” Barr said. “We are making sure that as we move forward, we protect their rights, we protect their health care and do all that we can to make sure that they have a good life while they’re working and a good life after they finish working.”

Endorsement in limbo

The UFT hasn’t endorsed a successful mayoral candidate since 1989, when it backed the city’s first Black mayor, the late David Dinkins. In 2013, the union endorsed Bill Thompson, who lost to then-Public Advocate Bill de Blasio.

Mulgrew backed Stringer in 2021, but Adams ultimately won the primary.

The union is planning to send out questionnaires next month to mayoral candidates who will then participate in a UFT forum.

A committee that oversees the union’s daily operations and the executive board recommend a candidate for endorsement, then the union-wide Delegate Assembly — chapter leaders and delegates — makes the final decision through a vote, according to the union. But rank-and-file union members believe that vote is a formality and that Mulgrew ultimately makes the decision.

If the union’s ultimate decision results in an endorsement of Cuomo, it would likely ruffle feathers.

He resigned in 2021 after being accused of sexual harassment, which he denies, and amid reports his administration tried to cover up nursing home deaths during the Covid pandemic. His past education agenda, which included an overhaul of the state’s teacher evaluation system, was unpopular among educators. And the union opposed his Tier VI plan, which raised the retirement age and reduced benefits for new state and local workers in an effort to decrease the amount the state spent on employee pensions.

Stringer, for his part, saw his 2021 mayoral campaign derailed by sexual misconduct allegations. Mulgrew stood by him, and the UFT’s parent union is among Stringer’s consulting and lobbying clients.

To win the union endorsement, Stringer would need to make a stronger showing in the polls, according to an individual familiar with Mulgrew’s thinking.

“He’s got a lot to think about before he endorses a mayoral candidate,” George Arzt, a political consultant, said, referring to Mulgrew. “If there is one person that stands out, I think he will go for them. If it’s Andrew, he’ll wait a little bit and go for Andrew.”

Mulgrew may be looking to tread carefully to avoid alienating more members, two former senior union officials and one rank-and-file leader told POLITICO.

“I don’t believe the membership of the UFT would approve of endorsing Adams because of the state of the public school system and the damaging decisions that have been made since he became mayor,” said Arundell, a former high-ranking union leader with extensive knowledge of the union’s endorsement process. “There is no way this membership will abide by endorsing Andrew Cuomo, the father of Tier VI.”

But two individuals familiar with Mulgrew’s thinking maintained the union’s elections have no impact on the process.

“With a split ticket, I don’t think he’s as concerned,” one of the individuals said. “If it was one on one, he’d be far more focused on that. With a split ticket, the math just isn’t there.”

Union officials declined to comment on Mulgrew’s plans, but denied that he has the final say.

“He gets the recommendations and he trusts us to ask those good questions and for our recommendations,” said Vincent Corletta, a member of UFT’s Queens political action committee, referring to the union’s endorsement process for races. “It’s always been me and my colleagues that are in the district talking to these politicians.”

The union’s endorsement remains highly sought-after, given its past record of contributing significant amounts of cash to political efforts.

Stringer — as well as state Sens. Jessica Ramos and Zellnor Myrie — told POLITICO they’re seeking the union’s endorsement. Michael Ceraso, deputy press secretary for Michael Blake, a former assemblymember, also said Blake wants UFT’s backing.

Lander, a left-leaning Democrat, said he would “love” to have teachers’ support. A City Hall spokesperson declined to comment on whether Adams has been in communication with Mulgrew.

Assemblymember Zohran Mamdani and attorney Jim Walden, who’s running as an independent, declined to comment. A spokesperson for Cuomo also declined comment.

“I see a very strong, powerful union, I see a very respected and accomplished labor leader and I expect that to continue,” Stringer said. “Whoever [is] the next mayor is gonna need an experienced leader to meet the educational challenges in the city.”

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