South Loop mail thief with 2-gram-a-day meth habit gets federal prison time for possessing postal service master key

CHICAGO — A federal judge has sentenced a suburban Chicago man to 366 days in prison for possessing a forged U.S. Postal Service master key that he and an accomplice allegedly used to steal “vast quantities” of mail from South Loop residential buildings in late 2021.

Dennis Maddox, 44, faced up to ten years in prison and a $250,000 fine, but U.S. District Judge Thomas Durkin sentenced him to far less time. Prosecutors had asked for 18 months, while Maddox’s attorney asked for no confinement beyond the week of jail and five months of home confinement he had already served.

The master key, also known as an “arrow key,” allows mail carriers to unlock entry systems and entrance doors on “nearly every apartment and office building through the City of Chicago,” as well as mail and collection boxes, prosecutors explained in a court filing.

Maddox borrowed the forged key and offered a driver gas money and methamphetamine to drive him and his alleged accomplice, Jeanie Newman, to “some of the better neighborhoods,” officials said. Late on December 22, 2021, they picked the South Loop.

Dennis Maddox (Chicago Police Department)

Maddox quickly emptied the contents of six banks of mailboxes, collecting over 250 pieces of mail from 107 customers, federal officials said. He would keep any cash in the mail and sell checks and bank cards to third-party fraudsters.

Chicago police officers responding to 911 calls about mail thefts in progress arrested Maddox and Newman in the 1200 block of South Plymouth. Maddox eventually pleaded guilty to theft in state court, receiving a sentence of one day from Judge Robert Kuzas, according to court records. Newman received six months of conditional discharge. Her federal case is still pending.

The federal charges are not considered double jeopardy because possessing the postal key is a separate criminal act, officials said.

In a sentencing memo, federal prosecutors argued for a longer prison sentence, citing Maddox’s “regular contact with the criminal justice system for decades.” His 16 criminal convictions include seven narcotics cases and six thefts or burglaries, the memo said.

His defense attorneys, Christopher Grohman and Carly Chocron, claimed in a defense memo that Maddox’s criminal activity is all related to his drug addiction. When he was arrested in the South Loop, Maddox was consuming about two grams of methamphetamine a day, the lawyers said.

Maddox and Newman “were stealing everything in sight to get money to buy meth,” said the memo. Despite his steady contact with the criminal justice system, state officials never provided Maddox with “robust” drug treatment, the attorneys claimed, yet he has been clean and sober since May 2022 under a federal program.

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Tim Hecke is CWBChicago's managing partner. He started his career at KMOX, the legendary news radio station in St. Louis. From there, he moved on to work at stations in Minneapolis, Chicago, and New York City. Tim went on to build syndicated radio news and content services that served every one of America's 100 largest radio markets. He became CWBChicago's managing partner in 2019. His email address is