Sam Stair arrest is part of a bigger landlord issue, Milwaukee officials say

Milwaukee elected officials say the recent arrest and charging of a Milwaukee landlord in a sprawling drug case showed the city needs to take problematic landlords and the tenants who report them more seriously.

Sam Stair, 52, owner of S2 Real Estate Group, was arrested by federal agents early on April 22 and charged with multiple drug charges stemming from renting houses to be used for drug trafficking. In the week since the arrest, elected officials and community groups responded with alarm and said it showed a need for more to be done against problematic landlords.

“I’m angry. I’m disappointed,” said Ald. Jose Perez, who represents parts of the city’s south side and is president of the Common Council. “We want these properties to be caught sooner.”

Stair owns and manages over 150 properties, which have over 500 units and are mainly concentrated on the city’s south side. The charges against him and 17 others suggest a wide-ranging operation where Stair would lease homes that would be used by drug dealers either as stash houses, for storing drugs, or as trap houses, for selling drugs to dealers, according to a 176-page criminal complaint.

Stair, whose properties are the frequent subject of tenant complaints, is accused of earning over $1.5 million as part of this operation, which included using these dealers to manage his properties, including finding those addicted to drugs to rent the units to, according to court documents.

The case has been under investigation since May 2024.

Stair’s arrest and the charges against him have been pointed to by community members and organizations as a clear example of a gap in the city’s safety. On April 26, the public safety organization Common Ground pointed to it when promoting a plan for improving safety on the city’s South Side.

In a statement, the group said “negligent landlords” like Stair are hurting Milwaukee neighborhoods “in order to maximize their profits.”

“The victimization of these neighborhoods is systemic,” said Jack Eckblad, Milwaukee County District 4 Supervisor, who endorsed the safety plan. “It erodes trust in institutions like the police, like the fire department.”

At that event, Danyell Austin, a tenant of Stair’s, told the Journal Sentinel she and other tenants are left uncertain of how to move forward or whether to continue paying rent. Austin rents a commercial storefront from Stair’s company S2 Real Estate Group on West Greenfield Avenue and South Layton Boulevard.

Community Advocates, a nonprofit that helps low-income families meet their basic needs, recommends that tenants hold on to traditional rent payments, like checks, until further notice. However, if tenants are able to pay through their online portal, they should continue to do so, as that is typically more secure, said Shawanna Lindenberg, the organization’s housing department manager. 

Austin has reported myriad concerns with the company to the council member in her district, JoCasta Zamarripa, mainly relating to unresolved maintenance issues which she continues to struggle with to this day.

In an interview prior to Stair’s arrest, Zamarripa told the Journal Sentinel she had received messages from a few constituents but was unaware of the severity of tenant complaints or Stair’s business model.

Austin said she’s not surprised that the city hadn’t acted against Stair before his arrest.

“He acts like he was untouchable,” Austin said. “He’s likeable, he has the money behind him, he knows that most people don’t have the financial stability to fight against him in court if it really comes to it.” 

Stair is not the first Milwaukee landlord charged for drug dealing. In 2017, Kenneth D. Churchill III pleaded guilty to a charge of distributing heroin.

He was a significantly less prolific landlord than Stair. Churchill operated 12 properties and half had a designation as drug houses, the Journal Sentinel reported at the time.

Stair’s arrest and prior incidents like Churchill’s show the need for more coordination between the city and more attention to residents’ concerns, Perez said.

“I don’t think we’re making the connection with some of the complaints we have in the neighborhood with an enterprise similar to what we’ve seen in the news – a drug enterprise,” he said.

Stair’s arrest gives the city the opportunity to build off that momentum and hold other problematic landlords accountable, said Milwaukee County District 14 Supervisor Caroline Gomez-Tom, who represents parts of the city’s south side.

While many were unaware of Stair’s actions, Gomez-Tom said tenants were reporting concerns and deserved to be listened to.

“Sometimes, unfortunately, its falls to deaf ears. Either they’re reporting it to police or they’re reporting it to elected officials,” Gomez-Tom said. “The need is there for stronger responses to even the smallest concerns. If one person is reporting it, many other people are seeing it.” 

Stair appeared in federal court on April 22 and remains in custody. He is due back in court for a detention hearing on April 27.

David Clarey is a public safety reporter at the Milwaukee Journal Sentinel. He can be reached at: dclarey@gannett.com.

Alyssa Salcedo covers Silver City, Layton Park and Burnham Park for the Journal Sentinel’s Neighborhood Dispatch. Contact: asalcedo@usatodayco.com.

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