Crime & Safety

Errant Text Messages Lead to Attempted Robbery Arrest

According to police, 17-year-old Greenfield thought he was texting a friend and letting him know where and how he could rob a man, but he was really texting a 12-year-old boy whose dad tipped off police.

Text messages first sent to a 12-year-old boy and then to a Milwaukee police officer led to felony robbery charges for a 17-year-old Greenfield man.

Jaime Jessup was charged with one count of conspiracy to commit robbery with use of force Thursday in Milwaukee County Circuit Court. If convicted, Jessup faces up to 7 ½ years in prison and $50,000 in fines.

According to the criminal complaint:

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On Oct. 25, a Milwaukee police officer received a call from a man who said his 12-year-old son had been receiving mysterious text messages. The man believed the text messages were related to drug dealing, and gave the phone to police.

A police officer reviewed the text messages and believed the person sending the texts was trying to set up a robbery or a theft from a drug dealer.

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For the next several days, the police officer exchanged texts with Jessup and found out Jessup thought he was texting a friend, the complaint said. According to police, Jessup was trying to help his friend retaliate against a man who had recently robbed Jessup’s friend of marijuana.

Jessup eventually agreed to show “his friend” (the police officer) where the man who took his marijuana lived so his friend could rob him. Through text messages, Jessup urged his friend to come to the house “strapped” because the man had guns, according to the complaint.

Jessup and “his friend” agreed on a location to meet, and when Jessup arrived, he was arrested by undercover police officers.


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