It happened on Saturday as officers were taking him to the Lake County, Illinois jail.
Officers in Park Ridge were taking Wesley Anderson to the Lake County, Illinois, jail Saturday when he managed to get away.
Anderson allegedly carjacked two different drivers with his handcuffs still on, then took off for Wisconsin.
Police in Wisconsin took him back into custody after a chase.
But a new video shows he gave a second escape attempt a go later that day.
Anderson was getting checked out at the hospital, where he's accused of trying to overpower two Kenosha County deputies.
The deputies were able to subdue Anderson, who has since been booked on multiple charges including battery of a police officer.