Joseph Weiss is on the brink of pleading guilty to charges of deceiving federal investigators about his brother's mob connections. The 43-year-old Oak Lawn resident was slapped with charges last year after allegedly lying about his brother James Weiss' affiliations with Frank “The German” Schweihs, a notorious mob enforcer. His attorney, Lisa Wood, indicated their readiness to accept a draft plea agreement presented by prosecutors, setting the stage for a May 20 change-of-plea hearing, as reported by the Chicago Tribune.

Joseph's brother, the politically wired James Weiss, previously found himself entangled in the law's grip for bribing two state officials aimed at passing legislation beneficial to his gaming machine venture. Poised to plead guilty later this month, Joseph's legal maneuver follows a thread of corruption leading to James Weiss serving a 5 ½-year prison sentence in Minnesota, set for release in August 2028. During a sentencing hearing, federal prosecutors highlighted James Weiss' ties to the Outfit as part of their argument, as recorded conversations had Joseph Weiss admitting his brother was “great friends” with Schweihs, according to the Chicago Sun-Times.

Adding layers to this complicated saga, indictments reveal that Joseph Weiss collected revenue for his brother's quasi-legal gaming machine operation. These charges paint a vivid picture of a man who not only managed the under-the-table earnings of a questionably lawful business but also obstructed justice when approached by law enforcement. It became clear during the investigation that Joseph Weiss had articulated on a federal wiretap that he explicitly knew of his brother's partnership with "a known long-time mob associate," referred to as Individual B., in statements obtained by the Chicago Tribune.

The deep dive into Joseph Weiss' federal indictment exposes how he lied to FBI and IRS agents in January 2022. When asked about any knowledge of individuals associated with Schweihs, he denied any relationships, especially concerning his brother and Individual B. He professed innocence, saying, "I swear I’ve been honest. I think I’ve given you what I know," only to be contradicted by his own voice on a wiretap declaring his brother and the hitman were "partners on everything," as the conversation was recounted in the Chicago Sun-Times.

Amidst these revelations, it's clear that the Weiss brothers are enmeshed in a web of political corruption, legal gambits, and alleged underworld ties. As Joseph Weiss prepares to concede to the weight of his deceits, the Chicago legal scene looks on, expectancy already entangled in the drama of corruption that never seems far from the city's storied streets.