Samuel Stair, owner of S2 Properties, is one of 18 people charged in a federal drug conspiracy case.
MILWAUKEE, WI — Federal agents arrested a Milwaukee landlord and 17 other people last week after prosecutors accused him of renting homes to drug traffickers who used the properties to store and sell drugs.
The case puts new attention on rental housing, nuisance properties and drug activity on Milwaukee’s south side. A 176-page federal criminal complaint says Samuel Stair, 52, owner of S2 Properties and S2 Real Estate Group, knowingly rented units to traffickers because it produced steadier income than lawful rental arrangements. Stair has been charged but not convicted.
Authorities arrested Stair on Wednesday, April 22, and the complaint was unsealed the same day in federal court. Prosecutors say the properties were used as stash houses, where controlled substances were stored before sale, and trap houses, where drugs were sold. The complaint lists charges that include conspiracy to possess with intent to distribute and distribute controlled substances, conspiracy to maintain a drug trafficking place and money laundering. Federal agents also charged Jeanette Lopez, described in court filings as a person who worked for Stair, along with 16 other defendants. A sign at S2 Properties near 29th Street and Lincoln Avenue still read, “Yes, we’re open,” after the arrests, according to local reporting.
The complaint says Stair sought out drug traffickers as tenants because they gave him a reliable flow of rent money. Prosecutors allege some traffickers also helped manage units, found people with drug addictions to rent to and used drugs as leverage when tenants could not pay. Federal filings also say Stair used traffickers for “security,” a term investigators said referred to illegal evictions. Investigators searched multiple properties tied to S2, including homes near 19th Street and National Avenue, homes near 21st Street and Pierce Street, and the company office near 29th Street and Lincoln Avenue. The full number of properties searched has been reported as at least 12. Officials have not said how many tenants were living in the units at the time of the searches.
The larger investigation began in 2024 and involved federal and local law enforcement agencies. Prosecutors said investigators used confidential informants, undercover agents and wiretaps. Court filings say raids at some properties turned up drugs, guns and cash. Inman, citing the complaint, reported that the drug activity included fentanyl, cocaine, marijuana and other narcotics, and that agents found cash, scales, hypodermic needles and firearms during arrests. Prosecutors also allege that by January 2026, nearly $225,000, or almost one-quarter of rental payments, came from properties linked to drug activity. The complaint says the money was deposited into accounts also used for lawful rent, which prosecutors allege helped hide the source of the funds.
S2’s reach across Milwaukee is part of the concern for city officials and neighborhood groups. Local reporting says S2 owns more than 150 properties, many on the south side, while other reporting says Stair owns or manages more than 500 rental units through S2 Real Estate Group and related entities. The complaint names 25 properties tied to Stair through limited liability companies and linked to drug trafficking, overdose deaths or alleged drug dealers. Since 2016, city records cited in real estate industry reporting show at least 360 violation orders filed against S2 Real Estate Group or related entities, involving nuisance behavior and unresolved maintenance issues. Those records are separate from the federal criminal case.
Milwaukee Common Council President José Pérez introduced three communication files after the arrests, saying the city needs a fuller review of how it handles problem landlords and nuisance properties. Pérez said he wants to hear from Milwaukee police and the Department of Neighborhood Services about nuisance declarations, drug-related crime data and property enforcement. He also requested information from the city attorney’s office about corporate ownership of rental housing. Pérez said in a statement that complaint-driven enforcement is not working well enough and that the city must examine how a suspected drug network could spread through rental properties.
Neighborhood advocates said the case matches concerns they have heard from residents. Common Ground, a nonprofit advocacy group, has spent the past year listening to people on Milwaukee’s south side about safety, housing and neighborhood conditions. Kevin Solomon, an organizer with the group, said members had already raised concerns about drug houses before the federal case became public. “Crime is an issue on the south side. Drug houses are an issue on the south side,” Solomon said. “The most horrific, vivid example to confirm everything we’ve said.” The group said it plans to release a south side safety plan with city and county leaders.
Stair was being held on a federal hold at the Kenosha County Jail after his arrest, according to local reporting. A detention hearing was scheduled for Monday, April 27. Prosecutors have said more charges could follow for lower-level members and associates of the alleged trafficking groups. The case remains in its early court stage, and the allegations still must be tested in federal court.
Author note: Last updated April 27, 2026.