Federal prosecutors and defense attorneys offered dueling portraits of controversial Milwaukee landlord Samuel Stair during an appeal hearing on Wednesday, May 20, as a federal judge weighed whether Stair should remain behind bars.
Federal prosecutors say Stair is the leader of a sprawling drug trafficking operation, and while behind bars, is continuing to engage in illegal activity.
But Stair’s attorney, Dan Adams, argues his client was never directly involved in the drug trafficking that federal authorities allege, and the evidence that he continues to conduct illegal activity while in jail is “speculative and insufficient.”
U.S. District Judge Brett Ludwig, who is presiding over the case, did not make an immediate decision on whether Stair will remain in custody. But he seemed unpersuaded by the prosecution’s argument that Stair could continue to operate the alleged drug trafficking ring with the proposed release conditions, such as house arrest and call monitoring.
“There is not another case in this district or anywhere else I’ve seen like this,” Ludwig said.
Stair, 52, of Hales Corners, was indicted on 11 counts, including conspiracy to sell drugs, keeping a drug house and money laundering. The sweeping federal case alleged that he knowingly placed drug dealers in his properties and took a cut of their profits.
If convicted, Stair faces a mandatory minimum of 10 years in prison and up to life behind bars.
The May 20 hearing was an appeal by Stair’s lawyer of Magistrate Judge Nancy Joseph’s order that Stair remain behind bars.
Assistant U.S. Attorney Katherine Halopka-Ivery argued that if released, Stair would be a danger to the community because he could find new drug dealers to fill the spots of those arrested and could solicit violence from those he employs in order to conduct his business.
Those arguments were “fanciful,” said Adams, Stair’s attorney, who argued that the proposed release conditions would prevent him from operating his business.
Adams filed an earlier motion for Stair’s release pre-trial, citing the landlord’s roots in the community and his minimal criminal history.
Under Adams’ proposed house arrest conditions, Stair would have no contact with co-defendants, be unable to access his drug-associated properties, have his devices monitored, be prohibited from using firearms, and surrender his passport.
But Stair’s “brazen” activity while under federal investigation, and since his arrest, shows he should not be allowed out of custody, according to federal prosecutor Halopka-Ivery.
Her filing says authorities are investigating Stair and, even while detained, he has “sought out updates on his codefendants, possible cooperators, and confidential sources.”
Before his arrest, Stair’s activity also shows why he shouldn’t be released, she said. She cited a comment to a confidential source where Stair discusses evicting tenants by asking the tenant’s drug dealer to “threaten the [expletive] out of him.”
“He is seeking out violence,” Halopka-Ivery said.
Federal prosecutors allege Stair’s business model was to rent his properties directly to drug dealers to be used as “stash houses” to store drugs or as “trap houses” to sell drugs, according to the 176-page criminal complaint filed against Stair and 17 others on April 21.
Stair also hired drug dealers to run “security” at his properties, carrying out “illegal evictions.” Renting directly to drug dealers also ensured a more reliable stream of income for Stair, prosecutors say.
Prosecutors say that Stair and his business, S2 Real Estate Group, are the “connecting fiber” of three drug trafficking organizations, which were operating through his company’s properties, and that Stair would tip off the leaders of these operations when he was notified by law enforcement that his properties were going to be raided.
During the investigation, which began in May 2024, law enforcement seized over one-and-a-half kilograms of fentanyl, three kilograms of cocaine, 800 grams of marijuana, and 60 grams of methamphetamine, along with multiple firearms, including a machine gun, according to the government response opposing Stair’s motion for release from jail.
“Just the amount of fentanyl seized during this investigation is enough to kill the entire population of Milwaukee and then some,” according to the government filing.
The company Smart Asset Management was hired to manage Stair’s properties while he’s in jail. Its owner, Adam McCarthy, said the funds left over from managing those properties will be held for Stair upon his release.
Prosecutors said earlier they are seeking to put all of Stair’s 150 properties under an independent receivership.
Receiverships have been used in civil cases but it is unusual in a federal criminal case.
David Clarey is a public safety reporter at the Milwaukee Journal Sentinel. He can be reached at: dclarey@gannett.com. John Diedrich is an investigative reporter for the Milwaukee Journal Sentinel. He can be reached at jdiedrich@gannett.com.
Alyssa Salcedo covers Silver City, Layton Park and Burnham Park for the Journal Sentinel’s Neighborhood Dispatch. Contact her at asalcedo@usatodayco.com.
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This article originally appeared on Milwaukee Journal Sentinel: Jailed Milwaukee landlord accused of drug trafficking seeks house arrest
Reporting by Alyssa N. Salcedo and David Clarey, Milwaukee Journal Sentinel / Milwaukee Journal Sentinel
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