Eighteen individuals, including Samuel P. Stair, the owner of Milwaukee-based residential and office real estate rental company S2 Real Estate, were charged this week in U.S. District Court for the Eastern District of Wisconsin with federal drug trafficking charges.

Stair, 52, owns more than 150 rental properties, predominantly on the south side of Milwaukee, according to the criminal complaint. He also manages several properties owned by third parties.

According to a criminal complaint, Stair was charged with conspiracy to possess with intent to distribute and distribute controlled substances; conspiracy to maintain a drug trafficking place; use of communications facilities to facilitate controlled substance felonies; and money laundering.

Since May of 2024, federal, state and local law enforcement agencies have been investigating several related drug trafficking organizations on the south side of Milwaukee that distribute fentanyl and cocaine. The drug trafficking organizations are connected because they operate by renting properties from S2 Real Estate, with the acquiescence and assistance of Stair and his employees, the criminal complaint states. Stair and his employees seek out drug traffickers to rent them S2 Real Estate properties to generate additional income, and the drug traffickers pay Stair for the properties and his assistance in evading law enforcement, the complaint states.

“Part of Stair’s business model is to rent properties directly to drug traffickers for their use as ‘stash houses’ (places to store controlled substances intended for distribution) and ‘trap houses’ (places from which to distribute controlled substances),” the criminal complaint states. “Stair seeks out drug traffickers as renters because doing so guarantees a steadier stream of rental income than he would otherwise obtain in legitimate rental arrangements. In some instances, Stair also relies on these drug traffickers to manage other rental units owned by Stair by, among other things, finding drug addicts to whom the rental units can be rented. This further guarantees rental income as it allows for traffickers to withhold controlled substances to which the renters are addicted if they do not pay rent.”

Others charged in the criminal complaint include Jeanette Lopez, 37, an employee of S2 Real Estate who serves as Stair’s primary assistant. She is charged with: possession with intent to distribute and distribution of controlled substances; conspiracy to possess with intent to distribute and distribute controlled substances; maintaining a drug trafficking place; conspiracy to maintain a drug trafficking place; use of communications facilities to facilitate controlled substance felonies; and possession of firearms in furtherance of drug trafficking.

“The news that Sam Stair of S2 Realty Group—the largest landlord on Milwaukee’s south side in terms of number of units—was arrested for alleged drug trafficking is a horrifying, vivid example of everything we have been saying about crime and safety issues on the south side,” nonprofit community advocacy organization Common Ground said in a news release. “These types of ‘quality-of-life’ crime issues—i.e., non-violent crimes like drug houses and sex work—are rampant on the south side. Our city’s crime statistics are not showing the full picture. Just one drug house can drag down an entire block, paralyzing the community, civic life, and cleanliness. Although the south side is vibrant and beautiful in so many respects as is, it could be even more so, were it not for crime.”

The news of Stairs’ arrest comes after the city of Milwaukee recently launched sweeping legal action against an out-of-state landlord, aimed at forcing long-delayed repairs or stripping control of hundreds of the company’s rental properties. The city filed public nuisance lawsuits against Highgrove Holdings Management LLC and its owner, David Tomblin. The cases target 138 properties and ask a judge to order repairs within 60 days or appoint a receiver to take over management. The city is also backing a separate foreclosure case filed by U.S. Bank involving another 85 properties tied to unpaid loans. Taken together, the actions could affect more than 200 properties across Milwaukee’s north side, making it one of the largest coordinated housing enforcement efforts in recent city history,

“These negligent landlords are hurting our neighborhoods, across the city, in order to maximize their profits,” Common Ground said. “It should not be that a corporation can so dramatically reduce the quality of life for a tenant, a block, and an entire neighborhood.”

In response to the arrest of Stairs, Alderman and Common Council President Jose Perez, whose district is located on the city’s south side, announced new legislation to address issues surrounding problem landlords.

“It seems clear that the system we have for complaint-driven actions against properties isn’t working. We must find a way to be more aggressive on the front end so this burden is not solely on residents,” Pérez said. “This new legal action shows that residents are being preyed upon and taken advantage of, and that is never okay. We need to have a thorough and open conversation about what is working, and not, and then take the necessary steps to improve these systems. I want to be perfectly clear, in short order, the city needs to align resources and systems to determine how one individual was able to orchestrate a city-wide drug network seemingly right under our noses. As a city are we maximizing all the tools at our disposal to deter such outcomes and if not, why not?”

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