Amid growing frustration surrounding the Chicago school system’s deteriorating finances, Chicago Public Schools CEO Forrest Claypool will face a symbolic “no confidence” vote by teachers beginning Monday.

The school district and City Hall are scrambling to find $129 million to keep schools open until the end of the year and also pay a $716 million pension bill in June. Exacerbating their woes are major delays in state payments owed to CPS. The state owes the school district as much as $467 million.

The vote by Chicago Teachers Union members is only the second of its kind in recent memory. The last time was in 2012, just before an historic strike. Union members voted in favor of the resignation of then-CEO Jean-Claude Brizard, but that ballot also asked teachers several questions about the school district’s contract proposals.

The current CTU leadership, in power since 2010, is known for its aggressive and outspoken advocacy. They voted in February to call for Claypool’s resignation. But next week’s vote will go far beyond CTU’s most involved inner circle.

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All 27,000 rank-and-file teachers and other members will be eligible to vote in schools Monday through Wednesday, a significant investment of time and money for the union. The CTU said it will deliver the results to City Hall on May 23.

To make their case to members, union leaders cite a long list of complaints against Claypool and district leadership. These include a “refusal to take the actions needed to properly fund and protect CPS,” imposing unpaid furloughs on teachers, and Claypool’s threats to end the year early as the district’s cash dwindled. CTU President Karen Lewis has been highly critical of CPS’ unsuccessful civil rights suit against the state over inequitable funding, calling it “ridiculous.” The suit was tossed out last month, less than three months after it was filed.

The union also is critical of privatization efforts, special education cuts and teacher layoffs. It also argues that outspoken teachers have been targeted for punishment.

Claypool, who has been CEO for nearly two years, said in response that “instead of creating a sideshow, the CTU should be fighting alongside us in the courts and in Springfield” for fair funding.

“Unlike Karen Lewis and [Gov.] Bruce Rauner,” Claypool added, “I don’t believe that fighting for the civil rights of 400,000 school children is ‘ridiculous.‘” This highlights a deep point of contention between the union and Claypool, who aggressively pushed the lawsuit as a way to force the governor into handing over more cash for CPS.

Mayor Rahm Emanuel added that Claypool “has handled a difficult job incredibly well,” he said in a statement Friday. The mayor said Claypool has his “complete confidence.”

That show of public support comes as sources tell WBEZ of rising tensions between CPS’ leadership and Emanuel’s office over how to pay to keep schools open till the end of year.

Two planned briefings for alderman on how the city and CPS will come up with the cash and keep schools open have been cancelled in recent days. It’s unclear when plans will actually be made and when they’ll be revealed.

Kate Grossman is a senior editor at WBEZ. Follow her at @WBEZeducation.