Repeat felon working as armed ‘security guard’ beat woman, threatened to shoot her outside Chicago liquor store: prosecutors

CHICAGO—As a prosecutor completed a petition asking a judge to keep Larenzo Bailey in jail on a new Class X gun charge, they summarized the state’s version of his life in a single sentence. It’s one you probably won’t see on LinkedIn.

“He is a lifelong resident of Cook County,” said the petition, “and has been contributing to society through drug sales and guns for decades.” Prosecutors further described Bailey as having an “extensive felony record for gun crimes and drugs spanning decades.”

Larenzo Bailey (Chicago Police Department)

So, it may be surprising for some readers to learn that Bailey was allegedly working as “armed security” for a liquor store when Chicago police arrested him Monday evening in the 3000 block of West Roosevelt. One of the store’s customers, a 37-year-old woman, called the cops after Bailey literally threw her out of the store, causing her to fall to the ground, a CPD report said.

While she was still on the ground, Bailey punched her in the face and then pulled out a gun, which he pointed at her, according to the report.

The cops saw Bailey outside the liquor store wearing a “security” vest and, unorthodoxly, a ski mask. As they patted him down, he flailed his arms and pulled away, the officers said in the report. After performing an “emergency takedown” on Bailey, the cops found a loaded handgun with an extended ammunition magazine inside his vest, officials said.

Prosecutors told Judge Susana Ortiz that Bailey had been convicted twice of being a felon in possession of a firearm as well as selling drugs by a park or school and battering police officers. Court records show he was charged with Class X armed habitual criminal and possessing a machine gun in 2020, but prosecutors dropped the case in 2022.

He is now charged with Class X armed habitual criminal again, along with misdemeanor charges of aggravated assault, battery, and resisting police.

Ortiz granted the detention petition.

A few days before Bailey’s arrest, Illinois legislators passed a bill that would change the crime known as “armed habitual criminal” to “persistent unlawful possession of a weapon.” They apparently believe people convicted of “armed habitual criminal” are getting bad reputations based on the name of the crime.

“It really comes out of the reentry space where people who don’t live in this world as we do [as state legislators] see the title of the offense and think it means something much more nefarious than it really does mean,” said Rep. Kelly Cassidy, whose district includes Uptown, Edgewater, and Rogers Park.

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CWBChicago was created in 2013 by five residents of Wrigleyville and Boystown who had grown disheartened with inaccurate information that was being provided at local Community Policing (CAPS) meetings. Our coverage area has expanded since then to cover Lincoln Park, River North, The Loop, Uptown, and other North Side Areas. But our mission remains unchanged: To provide original public safety reporting with better context and greater detail than mainstream media outlets. Our editorial email address is news@cwbchicago.com