A landlord charged in federal court with knowingly renting to drug dealers in exchange for kickbacks will remain behind bars, a federal magistrate judge ruled.
Sam Stair, who owns 150 properties, mostly on the city’s south side, is among 18 defendants charged in a sprawling, major drug-trafficking operation.
In a federal detention hearing on April 27, prosecutors argued that Stair should remain in jail because he is a danger to the community as the head of a drug dealing operation, in which he mingled illicit funds inside his legitimate business, S2 Real Estate Group.
“He was terrorizing, frankly, the south side of Milwaukee,” said Assistant U.S. Attorney Katherine Halopka-Ivery.
Prosecutors also sought to ban Stair from having contact with his business and to put all of his properties in a receivership.
The prosecutors could not cite another criminal case where the government has done that, underscoring the unusual nature of the charges against Stair.
U.S. Magistrate Judge Nancy Joseph asked prosecutors to file a motion on a possible receivership and argue it at a future hearing.
Stair’s attorney, Dan Adams, argued the government’s case is full of suggestive innuendo and failed to tie his client directly to drug dealing.
Adams said Stair is an upstanding citizen who built his company from nothing nearly 20 years ago. Adams also conceded being a landlord can be messy.
“You take tenants as they are,” Adams said. “He provides affordable housing for countless people who would have no place to go.”
Joseph said she was ordering Stair detained because of the allegations of major drug distribution and the risk those drugs, like fentanyl, pose to the community. Federal law assumes defendants will be detained in such cases.
Stair, 52, of Hales Corners, is charged with conspiracy, drug counts, maintaining a drug house and money laundering, according to a 176-page criminal complaint. He is the lead defendant in the case that has been under investigation since May 2024.
Dressed in inmate garb from Kenosha County jail where he is being held, he nodded to his wife and more than a dozen family and employees who filled the courtroom gallery.
As he shuffled out, Stair’s wife wept while another employee said, “Keep your head up, Sam.”
Stair is due back in court for a preliminary hearing on May 7.
Complex drug case alleged in federal court document
Prosecutors portrayed Stair as a savvy leader of a creative drug-dealing operation.
Stair invited drug dealers to live in his properties and sell drugs from those units, and then had the dealers fill other units with their drug buying customers.
Stair also utilized the drug dealers as security at his building, in which they sometimes used force to effect illegal evictions, Halopka-Ivery said.
Halopka-Ivery said Stair was brazen, tipping off dealers after he learned an investigation was underway and calling Milwaukee police to remove uncooperative dealers.
He kept a distance from the actual drug dealing, Halopka-Ivery said. She said undercover agents and informants along with a wiretap showed Stair’s true role.
“He was smart enough not to get dirty from those who may get caught,” she said. “This is someone at the top of a drug operation, keeping an arm’s length.”
Adams said Stair was unaware of the drug activity at his various properties, and that his office manager, Jeanette Lopez, who also is charged, was the one renting to drug traffickers for kickbacks.
Unusual move sought to freeze property
Federal prosecutors sought several ways to limit Stair’s connection to his business and properties.
Even though he is behind bars, if he authorizes any expenses over $10,000, it will need to be reported to the court.
The prosecutors also sought to bar Stair from having any contact with the business and to put all his units in a receivership, where another entity would have total control to collect rent and other operations.
Joseph, the magistrate judge, asked if there was a precedent for such a move in a federal criminal case and asked how it would work.
Assistant U.S. Attorney Julie Stewart said the receivership would be similar to the case of David Tomblin, who was sued by the Milwaukee City Attorney’s Office in March 2026.
The case alleges that Tomblin, owner of Highgrove Holdings Management LLC, allowed his roughly 260 properties to deteriorate, causing a public nuisance.
Joseph noted that is a state civil case and asked about a federal criminal precedent. Stewart said she knew of none.
The issue of a receivership will be in a motion from the government.
Who is Sam Stair and what kind of properties does he have?
Stair owns and manages over 150 properties with more than 500 units across Milwaukee, mainly concentrated on the city’s south side.
Federal agents identified at least 25 properties Stair owned that were associated with drug trafficking, drug overdose deaths, or known to be used by alleged dealers.
Stair has no serious criminal history aside from a drug-related offense which led to probation. Joseph said it was not relevant.
This story was updated to add a photo.
This article originally appeared on Milwaukee Journal Sentinel: Landlord who ‘terrorized’ Milwaukee with drug dealings remains jailed
Reporting by John Diedrich and Alyssa N. Salcedo, Milwaukee Journal Sentinel / Milwaukee Journal Sentinel
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