Milwaukee landlord charged in drug case released from jail

MILWAUKEE - A federal judge on Friday ordered Milwaukee-area landlord Sam Stair, who is accused of intentionally renting properties to drug dealers, to be released from jail.

Sam Stair

In court:

U.S. District Judge Brett Ludwig's conditions of release include home detention, GPS monitoring and no contact with co-defendants. Stair would be allowed to leave for work and other approved activities.

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"We're very glad that the judge applied the proper law to this set of facts. Given the government threw everything they could at Sam Stair, to have the judge look at that and take an objective view and say he's not a danger to the community, we all knew that," said Dan Adams, Stair's defense attorney. "Sam Stair has lived a very law-abiding life as a businessman in this community."

Stair has been in jail since April. He pleaded not guilty to all charges.

Federal investigation

The backstory:

Stair owns more than 150 rental properties – mostly on Milwaukee's south side and suburbs – through his company, S2 Real Estate. Those properties include more than 1,500 rental units.

According to prosecutors, Stair intentionally sought out and rented to drug dealers who'd use the properties as stash houses and trap houses and saw them as a dependable source of income.

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Prosecutors said, in some instances, drug dealers would manage the rental units and find drug addicts to rent them to. If addicted renters couldn't pay the rent, drugs would be withheld. In some cases, drug dealers were used as security and to carry out evictions.

The money would then be put into bank accounts for Stair's legitimate business, according to court filings. By January 2026, nearly $225,000 – almost a quarter of all rental payments – came from drug-associated properties.

The sweeping investigation involved the use of confidential informants, undercover agents and wiretaps. In one instance, prosecutors said Stair tipped off renters of a West Allis bar that police were investigating drug activity.

In total, 18 people are facing federal drug charges in connection to the larger case.

Judge's order

What they're saying:

In his written order Friday, Ludwig said trafficking drugs is serious and dangerous, but the government does not accuse Stair of selling drugs, just seeking out and renting to drug dealers:

"Given the presumption of innocence, detention prior to conviction is not supposed to be the default. Instead, a court should order a defendant detained only if it finds there are no conditions or combination of conditions of release on bond that will reasonably assure the appearance of the defendant and the safety of the community.

"The offenses with which the government has charged Stair are unquestionably serious and there is strong evidence supporting many of the underlying factual allegations. 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 government has not credibly identified specific dangers posed by Stair’s release on bond or explained why the conditions proposed by defense counsel would not assure the safety of the community.

"After a de novo review of the entire record, the Court concludes that the government has not demonstrated by clear and convincing evidence that Stair himself, subject to individualized conditions of release, is a danger to the community."