Milwaukee County and the City of Milwaukee are staring down another round of structural budget shortfalls, with city services under pressure, and looming tax increases—even after a major sales-tax hike was sold as the solution to decades of pension and fiscal problems. As County Executive David Crowley, the Democratic nominee for governor, prepares his 2027 budget, the numbers show it’s in real trouble rather than the turnaround story his administration has claimed.
County Comptroller Bill Christianson forecasts project a $50.8 million structural deficit for 2027, with the gap averaging about $34 million annually and potentially reaching roughly $169 million by 2031 if current trends hold. Expenditures are expected to outpace revenues as one-time federal stimulus funds dry up, wage and benefit costs continue climbing (salaries rose more than 34% from 2021–2025), overtime numbers remain high, and the Milwaukee County Transit System faces a multi-million-dollar “fiscal cliff.” The transit system alone is looking at a $15–16 million shortfall next year after stimulus exhaustion, raising the prospect of further service reductions.
This comes after Wisconsin Act 12 in 2023, which Crowley championed. The law increased shared revenue and authorized Milwaukee County to impose an extra 0.4% sales tax (raising the county rate) primarily to address longstanding pension liabilities stemming from earlier scandals and underfunding. Officials directed much of the new revenue toward pensions and related obligations. Property-tax levy increases have also been used, and the county has made targeted cuts and efficiencies. However, the structural gap has reappeared quickly once temporary federal aid and the initial sales-tax “savings” were absorbed into ongoing operations.
City finances show similar problems. Milwaukee faces a sizable gap between desired spending and available funds. Reports have cited figures in the $90–100 million range for recent cycles with police, public works, and other core costs rising and cash reserves playing a role in bridging the gap. A new five-year city financial forecast released around this time reveals longer-term problems ahead. Christianson tells Fox 6 the city will need the state’s help to fix this problem.
Crowley’s record includes higher local taxes, reliance on temporary federal dollars, wage growth that outstrips revenue capacity, and recurring deficits that force either cuts or further tax hikes. Recent reporting shows plans for significant property-tax levy growth heading into 2027 as one tool to close the gap, alongside department spending cuts.
As he campaigns on experience managing a large government and delivering results, the county’s ongoing structural deficits, transit problems, and tax issues paints clear contrast for Tom Tiffany, Republican nominee for governor, who argues that the same blueprint should not be scaled statewide. Milwaukee county’s books offer a concrete test of the fiscal management he is asking Wisconsin voters to endorse.
