A debt collector has sued Democratic state Rep. Kalan Haywood Jr. for nearly $6,000 in unpaid credit card debt, but the 27-year-old Milwaukee legislator insists he owes nothing.
Absolute Resolutions Investments filed a small claims lawsuit against Haywood in Milwaukee County Circuit Court in April 2026. The complaint seeks approximately $5,600 plus post-judgment interest and legal expenses. The debt originated with U.S. Bank before being sold to the collection agency. The filing alleges Haywood repeatedly failed to make required payments over a 12-month period.
Haywood was summoned to appear in court on May 15 but did not show up. His next scheduled court date is June 18. Haywood’s defense has been to deny owing any such debt and to claim he has not defaulted on any credit cards.
Haywood has represented Milwaukee’s 16th Assembly District since winning election in 2018 at age 19, making him one of the youngest state legislators in Wisconsin history. He serves as Assistant Minority Leader and receives a base salary of $60,924 in 2026, set to increase to $64,023 for the following term, which is nearly $20,000 more than the average household income in his district. Despite the steady public paycheck, the lawsuit portrays a pattern of missed payments on personal credit card obligations.
The situation has fueled comparisons to the legal troubles of Haywood’s father, prominent Milwaukee real estate developer Kalan Haywood Sr. In 2019, a woman identified in court documents as Jane Doe reported to Milwaukee police that Haywood Sr. had raped and possibly drugged her. Haywood Sr. has denied the allegations.
Haywood Sr. was never arrested or charged, but the investigation drew intense scrutiny after Milwaukee police admitted mistreating the accuser and failing to properly notify her of case developments. The victim sued the Milwaukee Police Department, and the case was eventually settled. The state Department of Justice took over the investigation. A police interview video involving Haywood Sr. was leaked to the public, exposing significant dysfunction within the Milwaukee Police Department and the Fire and Police Commission.
Around the same period, Haywood Sr.’s development firm received millions of dollars in city-backed loans and taxpayer support for projects, including after the sexual assault investigation had already begun. Critics at the time questioned whether corrupt political connections shielded the developer from greater accountability.
Six years after receiving a $3.85 million city loan to convert the historic former Sears store at 2100 W. North Ave. into the boutique Ikon Hotel and conference center, Kalan Haywood Sr.’s development group failed to deliver on the project. The hotel plan fell through, and in 2023, Haywood and his partners pivoted to a new vision for the 7-acre site, including a brewery, an art gallery, offices, and market-rate apartments, though that plan also failed.
Now a third plan has surfaced, as Haywood’s group, HG Sears LLC, is still several months behind on repaying the original city loan. Haywood Group LLC has teamed up with the Milwaukee nonprofit Thirty Six Blocks Inc. to apply for affordable housing tax credits through the Wisconsin Housing and Economic Development Authority. The application seeks support for 46 apartments at the site, which is now being rebranded as Sears Market Square. Just days ago, the Wisconsin Housing and Economic Development Authority announced the project would receive federal and state affordable housing tax credits.
For a young legislator who rose quickly through Milwaukee Democratic politics, the credit card default lawsuit and flat denial of responsibility now sit alongside his father’s long-standing legal cloud. Both father and son have now faced serious questions about personal accountability while benefiting from positions of public trust and influence in the city.
