Milwaukee County Executive and Democratic gubernatorial nominee David Crowley isn’t ruling out another tax increase as his administration prepares to unveil its 2027 budget proposal.
Following a speech at the Wisconsin Counties Association, WISN’s Matt Smith asked Crowley whether his upcoming budget, expected to be released in the coming weeks, would include a tax increase. Crowley refused to answer the question directly.
“So there could be a tax increase in your next budget proposal?” Smith pressed.
“We are still going through the budget proposal right now,” Crowley responded. “You’ll see it when we release it.”
The exchange comes as Crowley’s tax record in Milwaukee County has emerged as an issue in the governor’s race. His opponent, Tom Tiffany, has repeatedly hit Crowley over the airwaves and in interviews for his history of raising taxes on Milwaukee County families launching another ad late last week featuring a Milwaukee County resident detailing Crowley’s record as County Executive.
Since Crowley took office, Milwaukee County’s property tax levy has increased in every budget year except one. The exception came after Wisconsin Act 12 allowed the county to nearly double its sales tax from 0.5% to 0.9%, giving Milwaukee County the highest sales tax in the state. The additional sales tax revenue helped finance a one-year reduction in the property tax levy, but the levy began climbing again the following year.
Despite significant tax increases under Crowley’s leadership, Milwaukee County’s financial problems haven’t disappeared.
County projections show significant structural deficits in the years ahead, while the Milwaukee County Transit System is bracing for a potential 25% reduction in service beginning in 2027. Transit officials currently project a roughly $15.7 million shortfall next year, growing to $37 million by 2031. This is due, in large part, to a roughly 33% fare-evasion rate within MCTS, meaning that 1 in every 3 riders are not paying. MCTS has taken efforts to reduce fare evasion to mixed results.
Crowley has turned to Nicholas Sinram to help navigate those challenges, appointing the former Milwaukee Public Schools budget director to lead the county’s Office of Strategy, Budget and Performance earlier this year.
Sinram’s tenure at MPS overlapped with significant financial turmoil at the district. MPS ran a $46 million deficit and failed to submit required financial reports to the Wisconsin Department of Public Instruction on time, resulting in the state temporarily withholding aid. The reporting controversy also contributed to the resignation of former Superintendent Keith Posley.
The scale of the challenge facing Sinram and Crowley is already visible in Milwaukee County’s preliminary 2027 numbers.
According to the county’s 2027 Requested Budget Summary, departments collectively requested approximately $2.41 billion in spending. Those requests would require a property tax levy of roughly $389 million — about $80 million, or 26%, more in property-tax funding than was included in the county’s 2026 adopted budget.
Those figures represent departmental requests rather than Crowley’s final recommended budget, which is due by October 1st.
Whether he will turn to taxpayers to help close the gap remains an open question.
