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Monday, Oct 26, 2026

Did a Milwaukee County health insurance contract lapse under David Crowley’s administration?

Tom Kertscher / Wisconsin Watch, Wisconsin Watch
yes

A health insurance contract covering Milwaukee County employees lapsed in December under David Crowley, who has been county executive since 2020.

Crowley, a Democrat, faces Republican U.S. Rep. Tom Tiffany in the Nov. 3 election for Wisconsin governor.

A top county attorney said the failure to renew the contract put the county at “catastrophic risk.” 

But the 5,100 employees, dependents and retirees continued to be covered under the expired contract until a new one was approved in February.

Crowley blamed a top human resources official and fired him. He pledged to improve contract procedures.

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