Two Charged In Armored Truck Murder Also Murdered Accomplices

by Judd Mustin and J. J. Quincannon, The Chicago Times

November 18, 2021

Antwon Montgomery and Deandre Jennings

CHICAGO — Two men involved in an armored car robbery that killed a security guard and injured another on Chicago’s South Side also robbed a cellphone store before turning their guns on their accomplices.

According to Judge Charles Beach, the “brazen operation” conducted by Antwon Montgomery, 19, and Deandre Jennings, 21, could place the pair in prison for the rest of their lives if convicted of killing a GuardaWorld guard and the execution of two accomplices.

According to Chicago police, the GuardaWorld employees were loading cash into an ATM at a Bank of America branch in the 200 block of West 83rd Street around 10:20 a.m. Monday when a stolen Lincoln sedan carrying four people, including Montgomery and Jennings, pulled up.

Montgomery and Jennings allegedly exited the vehicle and demanded money from the guards at gunpoint.  Montgomery grabbed a case containing $50,000 to $80,500 that a 46-year-old guard was holding.  While Montgomery struggle take the case from the guard a third person emerged from the Lincoln armed with a rifle.  The three then allegedly started shooting at the guards.

CPD said the robbers were unable to take the cash and fled after returning to the Lincoln.  A short time later, a witness saw an armed Montgomery and Jennings exit a dark-colored sedan and enter a parked Buick SUV.  The witness wrote down the Buick’s license plate number before it drove away into a strip mall in the 6700 block of South Stony Island Avenue.

According to CPD, Montgomery exited the Buick and allegedly robbed a Boost Mobile store, taking cash from a register and multiple cellphones.  About an hour after the armored truck robbery, CPD received a report of a traffic crash and gunfire in the 8700 block of South Saginaw Avenue.

Officers arrived at the scene and discovered the body of Naiqwon Harper, 21, of Englewood, in the driver’s seat of the Buick.  George Holmes, 27, was found shot in the front passenger seat as well.

CPD said Harper and Holmes were involved in Monday’s armored truck robbery and are suspected of stealing the Lincoln sedan used in the crime earlier that day at gunpoint.

Prosecutors said the Buick was registered to Harper’s girlfriend.

CPD responded to an eyewitness that reported seeing Montgomery and Jennings run from the Buick and into a building on the block after the crash.  After the two were arrested, investigators discovered handguns, a rifle, cash, and clothing used during the robbery.  In addition, shell casings discovered at the scene of the armored truck robbery matched weapons discovered inside the building, as well as several Boost Mobile phones inside the Buick.

Montgomery and Jennings were ordered held without bail on Thursday after being charged with first-degree murder, attempted murder, and robbery.

Jennings and Montgomery are scheduled to appear in court again on December 6.