WARNING: This video may be disturbing to some viewers. Watch at your own discretion.
Surveillance video obtained by FOX 32 News shows a white sedan driving east on Webster and turning onto Wayne Avenue before coming to a stop. A person in a light-colored hoodie gets out and moves to the corner of a building at the intersection where he peeks around the corner down the sidewalk.
A man in his 20s is seen walking east on Webster Avenue when the robber turns the corner and pulls out a gun.
The man then hands over a bag and pulls out his phone. When the robber reaches for his phone, a struggle ensues and the pair falls into the intersection.
A second person gets out of the car and stands over the victim who is pinned down to the ground by the robber.
"What's the password?" the robber asks before firing one shot into the victim.
He asks him again for the password before shooting the victim a second time.
"Give me the password, man. What's the password?" the robber asks.
The victim, screaming in pain, struggles to give him the password. The robber then shoots him a third time before getting in the vehicle and driving away.
The victim suffered two gunshot wounds to the back and one gunshot wound to the head, police said.
He was taken by paramedics to Illinois Masonic Medical Center where he was listed in critical condition, police said.
Ald. Brian Hopkins (2nd) said in a message to constituents that residents have been assisting police in their investigation.
He said residents were "extraordinarily helpful in providing their surveillance video to the lead detectives. One observant neighbor even discovered some additional evidence and immediately brought it to the attention of investigators."
Hopkins condemned the act of violence and call for more police resources in the neighborhood.
"This lawlessness has to be stopped!" Hopkins wrote in the message "No neighborhood is immune to this criminal behavior. I have discussed the immediate need for additional tactical teams and patrols in the Lincoln Park area with the Chicago Police Department."
No one is in custody as Area Three detectives investigate.
The Sun-Times Media Wire contributed to this report.