Man charged with trying to kill 2 Chicago cops is on bail for Florida home invasion where accomplice was shot in an exchange of gunfire with sheriff’s deputies

The man who is accused of trying to murder two Chicago cops at a West Side hot dog stand is on bail for a Florida home invasion where his alleged accomplice was shot during an exchange of gunfire with sheriff’s deputies, according to court records.

Kailon Harris-Caldwell put his hand in his pocket to get money to pay for a purchase at Original Maxwell Street, 3801 West Harrison, around 3:30 a.m. Friday. Prosecutors said a gun fell from his pocket when he pulled his hand out as a Chicago police officer stood nearby.

Harris-Caldwell picked up the gun and shot toward the officer’s head from close range, leaving the cop with a graze wound, according to the allegations. He then allegedly fired on the officer’s partner, who was seated in a marked patrol car on the restaurant parking lot. That officer suffered a gunshot wound to the leg.

Kailon Harris-Caldwell is charged with trying to murder two Chicago. police officers at a West Side hot dog stand. | CPD

Prosecutors said Harris-Caldwell ran from the scene, but police found him hiding nearby. He allegedly left his car and his phone at the restaurant, they said.

Harris-Caldwell is charged with two felony counts of attempted first-degree murder, felony possession of a controlled substance, and misdemeanor manufacture-delivery of cannabis.

He did not attend his bail hearing on Sunday because he was hospitalized with back pain, a police officer told Judge Kelly McCarthy.

McCarthy set bail at $1 million cash, meaning Harris-Caldwell must post a full $1 million in cash to get out of jail. State law generally bars judges from holding defendants without bail if they are not physically present for the hearing.

Harris-Caldwell has a pending home invasion case in Lake County, Fla., northwest of Orlando.

His alleged accomplice in that crime, Sebastian Bradwell, was accused of firing a rifle at Lake County sheriff’s deputies as they arrived at the home in June 2018. Deputies returned fire. Bradwell was shot but survived.

Harris-Caldwell was arrested at the scene of the alleged crime, which local authorities called a “targeted attack.”

The Lake County sheriff’s spokesperson called Harris-Caldwell and Bradwell “very bold and brazen and unfortunately that’s just a reality of the times we live in right now.”

Florida court records indicate that Harris-Caldwell’s bail was $30,000, and the case was set for trial this month.

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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