Four more robbery charges for man who skipped electronic monitoring in March

Preston Gresham (inset) and a surveillance image of the Loop robber. | Chicago Police Dept

A man who was charged with robbing three businesses in the Loop while he was supposed to be on electronic monitoring in March is now accused of robbing four more boutiques in Lincoln Park, River North, and the suburbs that same month.

Gresham is now charged with robbing It’s Sugar and Jayne. | Google

Prosecutors have now charged Preston Gresham, 57, with robbing Jayne boutique at 2707 North Clark on March 18th and It’s Sugar at 1538 North Clybourn on March 14th, according to court records.

Since being arrested on the Loop robberies March 20th, Gresham has also been charged with the armed robberies of Close Knit in Dolton and Thrift House in Evanston on January 22nd, records show. Gresham was supposed to be on house arrest at the time of the January robberies.

Altogether, Gresham is charged with robbing eight businesses since last autumn. Seven of the robberies occurred while he was either on electronic monitoring or AWOL from the program, according to court records.

Gresham’s legal problems began in  October 2017 when he was accused of robbing a suburban KFC restaurant of $179 at gunpoint. He was charged with three counts of Class X felony armed robbery with a firearm, three counts of aggravated robbery and violation of bail bond. His girlfriend posted 10% of his $100,000 bail and Gresham went free.

In February, the girlfriend asked a court to revoke Gresham’s bail and to return her money because he had allegedly battered her. The court agreed. But Gresham skipped a March 1st court date for the KFC robbery and he was declared AWOL from electronic monitoring, according to court records.

Four days later, Gresham’s latest robbery spree began. In each case, he allegedly approached a clerk, and either displayed a handgun in his waistband or implied that he was armed, according to prosecutors:

• March 5th robbery of a women’s boutique in the 300 block of North Michigan
• March 7th robbery of another boutique in the 300 block of North Michigan
• March 14th robbery of It’s Sugar
• March 18th robbery of Jayne
• March 20th robbery of  Dunkin’ Donuts at 400 South Financial Plaza in the Loop

Investigators suspect Gresham is also responsible for the March 10th robbery of Leg Appeal, a women’s boutique in the 2800 block of North Clark, but charges have not yet been filed in that case.

Gresham is currently being held without bail.

Court records show that Gresham pleaded guilty to nine armed robberies in Chicago in 1998. He was sentenced to 15 years in prison for each case, but the judge ordered the sentences to be served concurrently and Gresham was discharged from parole in 2012.

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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