Will Sherard, one of Milwaukee's most notorious landlords, dead at 83

The small white house at 2233 W. Capitol Drive has seen better days.

In a recent visit, a Journal Sentinel reporter saw that two side windows had been boarded up by the city with green panels, several others were broken, a padlocked metal gate prevented entry through the front door, and much of the lettering on one side of the W.J. Sherard Realty Co. sign overlooking Capitol was badly faded.

This building once served as the headquarters for the rental empire of Will Sherard — long one of the north side's largest and most notorious landlords.

Sherard died in August at age 83, leaving behind a handful of properties, a company that owes more than $15,000 in unpaid Municipal Court fines for building code violations, and a wrongful death lawsuit still under appeal.

Last year, a Milwaukee County circuit judge ordered Sherard to pay $1.35 million because of an electrical fire at one of his rental properties that killed two people. The fire was detailed in a 2021 Milwaukee Journal Sentinel investigation about landlords who fail to fix dangerous electrical wiring in their properties. The case is under appeal.

Sherard's company, Morocco Investments, slowed down its activities in the years preceding his death.

Sherard and his company owned about a half-dozen properties when he died, compared to more than 100 that he owned in 2016 when he was profiled in a Journal Sentinel series about landlords who target low-income residents as tenants and game the system by making nominal payments on large fines for building code violations.

"He was known for decades for the deplorable conditions of his rental units," Colleen Foley, executive director of the Legal Aid Society of Milwaukee said in a text to the Journal Sentinel. "And his properties shone a light on inequities in the system."

Vincent Bobot knew Sherard as a landlord who stood before him when Bobot was a municipal judge and later as a client when Bobot was an attorney in private practice.

"The positive thing thing about Will was that he rented to people that nobody else would rent to," Bobot said, including people who had evictions on their record. "The issue was what he did rent to them."

Bobot noted that people frequently called the landlord's name when Bobot walked with Sherard on Capitol Drive.

"Everybody on the north side knew him," Bobot said.

Bobot said about half the people who shouted out Sherard's name on Capitol were supportive and the other half were foes.

"There was a notorious side to him," Bobot said.

Sherard made the news in 2016 when the Journal Sentinel disclosed how Sherard and others routinely received Municipal Court approval to make nominal payments on thousands of dollars of building codes fines. Meanwhile, Sherard continued to buy more problem-plagued inner-city properties to rent to low-income residents.

In May 2016, the City Attorney's office objected to continuing Sherard's easy payment plan. In response, Municipal Court Judge Phillip Chavez ordered that Sherard pay $39,728 in building code fines within 60 days, plus an additional $24,822 one year after that.

Taxes and interest on Sherard's properties stood at $3,507 at the end of October.

Cary Spivak is an investigative reporter with the Milwaukee Journal Sentinel. He can be reached at or (414) 550-0070.

Chris Ramirez of the Milwaukee Journal Sentinel contributed to this story.