County Investing $2.5 Million in Housing Assistance for Homeless

Washington Park Townhomes construction. Photo by Jeramey Jannene.

Milwaukee County officials are trying to repurpose $2.5 million in rental assistance funding, anticipating that changes at the federal level will increase homelessness locally.

In May, County Executive David Crowley announced his administration planned to shift $2.5 million in federal HOME funds from an affordable housing project to a rent assistance program supporting housing for people experiencing street homelessness.

“This reallocation will connect unsheltered residents to housing and supportive services, putting them on a path toward stability, independence and a way forward,” Crowley said in a statement at the time. 

Milwaukee County’s Housing Division operates a “housing first” model for addressing homelessness that provides stable housing first, then works with a person to address the root issues that led to them living on the street. For years, Milwaukee has consistently had some of the lowest populations of unsheltered homelessness per capita, and officials credit their housing first approach for this.

But beginning in 2028, President Donald Trump’s administration will overhaul federal assistance for homeless programs, moving funds away from housing and toward transitional housing and shelters.

“That’s going to dramatically increase homelessness in our community,” James Mathy, housing division administrator, told supervisors on the Committee on Community, Environment and Economic Development on Monday.

Homeless individuals are far less likely to accept placement in a temporary living facility or homeless shelter than in permanent housing, Mathy told supervisors.

The proposal received unanimous support from committee members. If approved by the full board, it will shift $2.5 million in federal funding away from a stalled affordable housing development in South Milwaukee called Canal Transit Lofts to direct housing assistance. The affordable housing project, being developed by AK Development, never got off the ground. The financing agreement between the county and the group expired in March of this year.

“This would be one of the largest homeless investments in the county’s history for a single use like this for rental assistance,” Mathy said.

The funds will be used for tenant-based rental assistance, which acts as a housing voucher that follows a person wherever they manage to find housing. The housing division will deploy them in 2027 and “stave off” the effects of changes at the federal level, Mathy said. The $2.5 million would allow the county to provide housing for “several hundred homeless people,” extending the program through 2027 and potentially 2028, he said.

The tenant-based rental assistance program is “probably our best tool,” Mathy said. These vouchers were boosted by legislation authored by Sup. Shawn Rolland in 2025, creating the Landlord Incentives to Foster Tenancy (LIFT) program. It provides participating landlords financial guarantees covering property damage or lost rent in exchange for “screening flexibility” for renters using a housing voucher or county rent assistance program.

“That really made a big difference,” Mathy said. “We have running lists of vacancies by neighborhood. We did not have that a couple years ago… We’re able to really work with landlords in a different way. It’s led them to waive background checks, credit checks.”

However, with rents rising, the county has been unable to issue new tenant-based vouchers in 2026. The program’s budget has been used to maintain existing vouchers. The funding reallocation to enhance and extend the program will be voted on by the full board later this month.

“We firmly believe we can keep up our progress with this amount of money,” Mathy said.