Sam Stair, the owner of S2 Real Estate, cleans up a unit after a tenant’s abrupt departure on April 1, 2026, in Milwaukee, Wisconsin. “It was like a drug issue. They got raided by the police,” said Stair.
Sam Stair, the owner of S2 Real Estate, cleans up a unit after a tenant’s abrupt departure on April 1, 2026, in Milwaukee, Wisconsin. “It was like a drug issue. They got raided by the police,” said Stair.
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Federal judge orders indicted Milwaukee landlord Sam Stair be released

A federal judge has ordered Milwaukee landlord Samuel Stair freed from jail, overturning a magistrate judge’s order and putting Stair under house arrest as he awaits a possible trial on drug charges.

In a 10-page order issued May 29, U.S. District Judge Brett Ludwig found that the federal prosecutors failed to make a ‘clear and convincing’ argument that Stair should remain behind bars.

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Prosecutors had argued Stair should stay in jail based on the seriousness of the charges against him. They also alleged that Stair had been in contact with co-defendants since he has been locked up.

Stair’s defense attorney has argued Stair is not a threat and there have been no inappropriate communications from jail.

The federal probation office had recommended Stair’s release earlier in the case, but U.S. Magistrate Judge Nancy Joseph ordered him detained based on the seriousness of the charges.

Ludwig overruled that and said the government was “painting with a broad brush” in its arguments to keep Stair locked up. He found Stair is not a risk to flee or to the safety of the community, under the conditions of house arrest.

“Nothing in Stair’s personal circumstances and criminal history clearly and convincingly supports a finding that he is particularly dangerous, especially compared to the other defendants in this case and most defendants charged in connection with drug trafficking,” Ludwig wrote.

The judge went on to note that Stair is not accused of directly buying or selling narcotics, save one incident where a sale was discussed.

“Stair’s role in the alleged conspiracy was unique and unlike that of the other defendants in this case and most defendants in other drug trafficking conspiracies,” the order said.

First Assistant U.S. Attorney Brad Schimel said while his prosecutors “disagree with this outcome,” they will not appeal it.

A bail hearing for Stair was set before Joseph late Friday.

Since Stair has been jailed, Smart Asset Management was hired to manage his 500 properties.

Federal prosecutors said earlier in the case they may file a motion to put Stair’s properties under an independant receivership. Such independant receiverships have been secured by Milwaukee City Attorney’s Office, but is rare in a federal criminal case. Prosecutors have not filed a motion on that issue.

According to terms of the release, Stair will be on house arrest but can leave his home for “verified employment, legal, medical, religious, and other activities as approved by Pretrial Services.”

He cannot contact co-defendants or be in contact with any “alleged drug-associated premises or the tenants of said properties as listed in the government’s complaint.”

Sprawling drug case laid out in federal court

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.

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.

Stair’s company ‘connecting fiber’ among drug groups

At a May 20 hearing in front of Ludwig, prosecutors said 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.

Stair would tip off the leaders of these operations when he was notified by law enforcement that his properties were to be raided.

Stair’s attorney, Dan Adams, argued 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.”

Lugwig sounded skeptical of the government’s case for detention and some of the allegations against Stair that showed up in his order.

“The government’s evidence is strongest that Stair intentionally rented properties to tenants whom he knew intended to use them for drug dealing. If proven, this is a federal felony. The evidence of additional wrongdoing is less clear or convincing,” according to the order.

Ludwig wrote the charges against Stair are “unquestionably serious.”

“In our society, however, a defendant is presumed innocent and liberty is the norm and individuals should not be detained based solely on the nature of the charges against them,” the order said.

This story was updated with new information.

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.

Neighborhood Dispatch reporting is supported by Zilber Family Foundation, Bader Philanthropies, Journal Foundation, Northwestern Mutual Foundation, Greater Milwaukee Foundation, and reader contributions to the Journal Sentinel Community-Funded Journalism Project. Journal Sentinel editors maintain full editorial control over all content. To support this work, visit jsonline.com/support. Checks can be addressed to Local Media Foundation (memo: “JS Community Journalism”) and mailed to P.O. Box 85015, Chicago, IL 60689.

The JS Community-Funded Journalism Project is made possible through our partnership with Local Media Foundation, tax ID #36-4427750, a Section 501(c)(3) charitable trust affiliated with Local Media Association, and EnMotive, LLC, a subsidiary of USA TODAY Co., Inc. USA TODAY Co., Inc. is the parent company of this publication.

This article originally appeared on Milwaukee Journal Sentinel: Federal judge orders indicted Milwaukee landlord Sam Stair be released

Reporting by Alyssa N. Salcedo and John Diedrich, Milwaukee Journal Sentinel / Milwaukee Journal Sentinel

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