Milwaukee’s city attorney is under scrutiny after the police officers’ union criticized the office’s decision to reach settlements in police misconduct cases.

In a letter to city officials, Milwaukee Police Association President Alex Ayala pointed to costly settlements City Attorney Evan Goyke’s office approved and the union says raise questions over the office’s legal defense of police officers.

The targets of the criticisms include an assistant city attorney who missed a deadline in a case that ended in a $185,000 settlement and the office’s decision not to fight another case that ended in a $2.5 million settlement.

“It is not clear to us whether the City Attorney’s Office currently has a litigator with sufficient expertise or competence to actually litigate complex civil rights cases through jury trial,” Ayala’s letter to Goyke reads.

In a statement, Goyke defended his office’s work and said his office “remains committed to lawful, ethical and professional service, careful stewardship of taxpayer resources, and ensuring that the City of Milwaukee acts within the bounds of the law.”

“As an elected office, the City Attorney is accountable to the voters and has a professional obligation to provide independent, objective legal advice to City officials and departments,” he said. “Our attorneys make decisions based on the law, the facts and their ethical duties. We are charged with providing our clients with the highest level of legal service, and I am confident we meet that standard.”

In the statement, Goyke, in turn, voiced his disappointment that the MPA and its attorneys did not engage directly with him.

“I know them, we’ve met previously and I’ve offered a direct line to me if issues arise,” he said. “It’s unfortunate they’ve ignored that invitation and engaged in a political game instead.”

Since Goyke started a four-year term as city attorney in April 2024, his office has agreed to large settlements in the cases for Danny Wilber and Keishon Thomas. Both are among the city’s most expensive settlements ever.

Wilber’s was for $6.96 million and is the second largest ever. It was not mentioned by the police union. It came after the man spent almost 18 years in prison and was released after a court deemed his court hearing was unfair.

The settlement in Thomas’ case, however, was one of three cases the police union pointed to.

Thomas was a 20-year-old Milwaukee man who in 2022 died of a drug overdose while in police custody for about 16 hours. On Dec. 2, a $2.5 million settlement was approved in that case.

It came after Thomas spent 16 hours in police custody before dying. Officers were convicted of criminal charges in the incident and faced department discipline for their inaction. Officers failed to check on Thomas’ condition and did not send him to the hospital even after he told officers he ingested drugs.

The Thomas case was resolved quickly as it seemed likely the city would lose a verdict, Goyke’s statement said. Engaging in a lengthy litigation would “only delay the outcome, risk incurring greater costs, and withholding settlement from the children of a man that died while in the City’s care,” the statement said.

The other case mentioned was that of Sedric Smith, whom the city settled with for $180,000. That came after his lawsuit said he was stabbed by a man police failed to remove a knife from.

That occurred in 2024 when Smith was working as a hospital security guard, according to court records. It came after Smith and other security restrained a man who had become threatening toward him.

When police arrived, they called an ambulance for the man and did not take away a knife in his belongings, according to the court records. The man was taken to the hospital Smith worked at and later stabbed him.

Smith filed a lawsuit in February, and an assistant city attorney missed a response deadline in the case. U.S. District Judge J.P. Stadtmueller, who was overseeing the case, was critical of the missed deadlines.

In a court filing, Assistant City Attorney Naomi Sanders cited staffing shortages, a hefty caseload and a staffer failing to submit deadlines to her calendar as among the issues she was facing.

The case was headed to a default judgment before the city and attorney’s office reached the settlement.

Goyke acknowledged and took the responsibility of the error made in the Smith case, noting that there were “consequences for the error and improvements implemented to ensure it does not happen again.”

Ayala did not respond to a Journal Sentinel request for comment.

A spokesperson for the Milwaukee Police Department referred questions to the police union and Goyke’s office.

The union’s decision to point to the cases of Keishon Thomas and Isaiah Taylor drew criticism from the attorney who represented both.

To fight the Thomas case and others Ayala highlighted would be a waste of taxpayer money, attorney Mark Thomsen said.

“The Milwaukee Police Association should not be defending officers and former officers that pled guilty or were found responsible for their criminal conduct,” said Thomsen, an attorney with Gingras, Thomsen and Wachs. “The reputational harm to the Milwaukee police officers were the result of the officer’s criminal conduct, not the resolution of a case.”

In his letter, Ayala said Goyke’s handling of the Thomas case was part of the reason he was questioning the city attorney’s legal representation for officers. Ayala described the case as “very defensible.” He suggested it should’ve been taken to a federal jury trial.

“We believe that ineffective legal representation is the real reason that cases like Thomas are settled for astronomical sums,” he said.

The union should be “ashamed” of its defense of the officers involved in the case, Thomsen told the Journal Sentinel.

Thomsen also represented another case Ayala pointed to, that of Isaiah Taylor, the son of Lena Taylor, a Milwaukee County circuit judge and former member of the Wisconsin State Senate. The city paid out $350,000 in the Taylor case.

Taylor’s lawsuit said the officers racially profiled him and he was subject to unreasonable seizure and search.

At the time of Taylor’s arrest, he was 16 and delivering a turkey to a neighbor in December 2015 when two officers stopped him.

Officers frisked him, searched his bag and detained him in their squad car while they checked to see if he had any outstanding warrants, according to court records. Robberies had been reported in the area beforehand.

Officers involved in his arrest were initially cleared by a jury, but a federal appeals court granted Taylor a new jury trial on appeal. The city then settled the case.

Thomsen said the officers’ actions were unjustified and illegal.

The police union has previously not shied from criticizing the city’s handling of police misconduct settlements, which have a long history of being costly in Milwaukee.

In 2021, the city approved a $750,000 settlement in the case of former Milwaukee Bucks player Sterling Brown, after police grew confrontational and aggressive, including using a taser on him. Police body camera footage showed Brown staying calm throughout the incident and led to a rework of several police policies.

The police union and the Milwaukee Police Supervisors Organization were critical of that settlement, in the months before its final approval.

“We have no confidence in your ability to legally and ethically represent our members on, at the very least, this case,” a joint letter to then-City Attorney Tearman Spencer read in 2020.

The city has settled at least 290 of the cases since 1986, according to data provided by the City Attorney’s Office. That totals over $65.5 million.

At times, the cases’ costs have increased as the city has hired outside legal counsel to fight them. For instance, in 2025, the city hired a Chicago-based law firm for the Danny Wilber case that ended in a settlement.

That’s been the case from before Goyke’s tenure as well. In 2017, then-City Attorney Grant Langley spent $1.5 million to help with an illegal strip search lawsuit.

The city is self-insured, which means taxpayers bear the costs of any settlements.