CHICAGO (AP) — An order barring the president of the police union from making public statements encouraging members to disobey the city’s COVID-19 vaccine mandate expired after a judge on Monday denied a request to extend it.

Earlier this month, Cook County Judge Cecilia Horan granted the city’s request for a temporary restraining order. After hearing arguments Monday, she issued a written ruling denying the city of Chicago's renewal and expansion request saying the situation had “materially changed.”

City attorneys wanted the order extended to include other union leaders in addition to Fraternal Order of Police President John Catanzara, accusing him of continuing to speak out or having other union officials do so in his place.

“Mr. Catanzara continues to make statements that if not cross the line, come right up to over and certainly his toes are crossing the line,” Mike Warner, an attorney for the city, said. “These statements are adding gasoline to the fire. They are urging his members to engage in an unlawful act.”

City employees have to be vaccinated by year's end with few exceptions or risk losing their jobs. Most departments complied with an initial deadline this month to report their status, but the police department has lagged behind in the escalating legal fight with the city.

The city argued the union’s actions amounted to encouraging a work stoppage while union attorneys said the matter is part of a unfair labor dispute and the vaccine mandate was ordered without union input.

Horan said that the situation since the first injunction had changed since the Oct. 15 deadline to submit vaccination had passed and “the threatened work stoppage has not come to pass.”

Catanzara has directed members to defy the city’s requirement and been outspoken in recent days on social media and in person. He spoke Monday to dozens of of protesters gathered outside Chicago’s City Hall and during a City Council meeting.

“This is not the way a government is supposed to run. It is not a queen on that throne. It is a mayor,” he said during the meeting, adding that there'd be “hundreds” of officers defying the order.

He asked aldermen to back the union and support a proposal requiring council approval for policies that govern disciplining city employees, saying those who didn't would see challengers in the 2023 municipal election.

Chicago police leaders, who call the vaccine mandate a matter of protecting officers and the public, have said less than two dozen officers haven't complied with the order to the point of risking their employment. The city's order allows for a temporary window of regular COVID-19 testing at the employee’s own expense until vaccines can be administered.

Police Superintendent David Brown said Monday that 23 department employees were placed on “no-pay status” for failing to comply with the order. About 70% of department employees have reported their vaccination status, of which 80% are fully vaccinated, numbers that have recently increased.

“We want to stay focused on protecting the people of Chicago. That includes the police officers of this department,” Brown said. “So we really see this as a life-saving effort for police officers ... Part of that means following through on the vaccine mandate.”

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Associated Press reporter Kathleen Foody contributed to this report.