Man gets 33 years for trying to murder 2 Chicago cops at West Side hot dog stand

Man Sentenced to 33 Years in Prison for Shooting Chicago Police Officers

A man who shot two Chicago police officers after one of them saw a gun tumble from his pocket as he tried to pay for his order at a West Side hot dog stand was sentenced Friday to 33 years in prison.

Kailon Harris-Caldwell, 28, pleaded guilty to two counts of attempted murder in exchange for concurrent 33-year terms handed down by Judge Thomas Byrne, according to court records.

Prosecutors say the incident unfolded around 3:30 a.m. on March 4, 2022, when Harris-Caldwell reached into his pocket to pay for an order at Original Maxwell Street, 3801 West Harrison Street, as a Chicago police officer stood nearby. A handgun with an extended magazine fell from his pocket when he pulled his hand out.

Harris-Caldwell picked up the gun and immediately fired at the officer’s head from close range, prosecutors alleged, leaving the cop with a graze wound. He then opened fire on the officer’s partner, who was seated in a marked patrol car in the restaurant’s parking lot. That officer was struck by a gunshot to the leg.

Harris-Caldwell fled the scene, but back-up officers found him hiding nearby. He allegedly left both his car and his phone at the restaurant.

The shooting was captured on video, and prosecutors said lab technicians matched shell casings found at the restaurant to a gun recovered when Harris-Caldwell was arrested.

At the time of the Chicago shooting, Harris-Caldwell had a pending home invasion case in Lake County, Florida, northwest of Orlando. His alleged accomplice in that crime was accused of firing a rifle at Lake County sheriff’s deputies when they arrived at the home in June 2018. Deputies returned fire, and the accomplice was shot but survived.

Harris-Caldwell was arrested at the scene of the Florida incident, which local authorities described as a “targeted attack”. A Lake County sheriff’s spokesperson at the time called Harris-Caldwell and his alleged accomplice “very bold and brazen.” Florida court records show his bail in that case was set at $30,000, and the case had been scheduled for trial the same month he shot the Chicago officers.

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