Alderman Won Office Owing Property Taxes

When newly elected alderman DiAndre Jackson took his oath of office on April 16, he was in an unusual position: His new employer was suing him for unpaid property taxes.

On April 2, Jackson won 61% of the vote, becoming the new alderman for District 7, which includes Century City and several surrounding central city neighborhoods. On April 9, the City of Milwaukee filed a small claims court action against Jackson for $1,675 stemming from his unpaid 2022 property taxes.

Is it something people should be concerned about?

“No. Just betting on myself,” said Jackson in an interview last week. “I have nothing to hide.”

In October, Jackson, 38, lost his job of 16 years when Master Lock eliminated his position. He was a high-profile blue-collar worker at the plant at 32nd and Center streets, rising to become head trustee of UAW Local 369 and chairman of the Coalition of Black Trade Unionists. When President Barack Obama visited the plant in 2012 to promote American manufacturing, Jackson was given the honor of introducing him. But in May 2023, Master Lock announced it was closing the plant.

Jackson used a severance package to pay some of his bills, including previously unpaid taxes and related court costs, and also loaned his campaign $9,500. But it wasn’t enough he said. “Every bill isn’t going to make it, you know how that goes.” He said he consciously made the decision to delay paying off some of the tax debt until after the campaign and planned to ultimately do so by returning some of his campaign loan. Candidates may legally repay loans to themselves, but may not use other contributions for personal expenses like tax debt.

Jackson reported raising $17,142 in his most recent campaign report, which covers a period from Feb. 6 to March 18, and $25,355 since Jan. 1. As of March 18, his campaign had $17,603 on hand. Donors to his campaign, which labor groups strongly backed, include County Executive David Crowley, Congresswoman Gwen Moore, attorney Mark Thomsen, marketing executive Nancy Hernandez, real estate developers Michael Klein and Derek Schneider, fundraiser and Common Ground member Bob Connolly, gas station owner Baljinder Dhillon and business owner Mandeep Kler. He worked with Nation Consulting on his campaign.

On April 16, Jackson told Urban Milwaukee he would pay the unpaid taxes by the end of the week. The next day, he paid off the 2022 balance subject to the court action. The 2023 taxes, not yet subject to court action, remain outstanding for $1,501 according to the city’s online tax system.

The new alderman’s run for office started with several open tax claims against him. The city filed annual property tax claims against Jackson between 2013 and 2016. According to city property tax records, he had paid off the bulk of those claims in 2017 and, according to court records, paid off any remaining costs to reach full satisfaction on March 4.

The property at the center of Jackson’s tax issues is an 828-square-foot structure on the 2700 block of N. 24th Street. Currently assessed for $33,400, Jackson purchased the house in 2004 through a U.S. Department of Housing and Urban Development program. The house is located just outside of the 7th District in the Amani neighborhood, which straddles both the 7th and 15th districts. Jackson, according to multiple public records, has since relocated to a rented home on the 3500 block of N. 58th Blvd.

The new alderman previously encountered tax issues with a second property. From 2011 to 2016, Jackson owned a duplex at 2449-2451 N. 21st Street. The city ultimately took the property via tax foreclosure, but only after it also demolished the home. According to city assessment records, it was the third such time since 1995 the city had used its in rem tax foreclosure power on the property. The now-vacant lot remains in city ownership, one of eight such properties on the block. A search of city property tax records does not indicate Jackson owns any other properties.

Tax issues aside, Jackson is ready to get to work.

He told Urban Milwaukee he’s looking forward to seeing the positive impact the new 2% sales tax has on public safety staffing. He’s also interested in addressing flooding near N. 60th Street and W. Capitol Drive and other quality-of-life issues. “I’ve got about 200 pages of notes and I’m just going to start chipping away at them,” said Jackson.

In February, Jackson won a four-way primary where each candidate got at least 21% of the vote. He faced Jessica Currie in the general election, who also used her lived experience as part of her appeal to voters. Currie was once a homeless teen mother and high school dropout who later founded Missionary Currie for Women and Children, a nonprofit organization that provides emergency shelter and supportive services to women and children.

Khalif Rainey had served as the 7th District representative since 2016 before announcing in December he wouldn’t run for reelection.

The voting age population of the 7th District, according to 2021 redistricting data, is 8% white, 84% Black, 4% Hispanic and 2% Asian. Council members are elected to four-year terms and paid $84,205 annually.

UPDATE: An earlier version of this article misstated Jackson’s current street of residence.