ABC7 has learned Heriberto Viramontes has received settlements of thousands of dollars from the City of Chicago and Cook County in recent years. Those settlements were reached after Viramontes claimed he was the victim of police abuse.
Even though officers denied those claims, Viramontes received cash settlements totaling $18,000.
Police say Natasha McShane and Stacy Jurich were beaten in Bucktown without warning and without hesitation.
Viramontes is now in jail, charged with the crime, the latest of nearly 20 he's accused of committing in recent years. But on two occasions, it was Viramontes who was able to cash in by claiming he was a beating victim.
The mugshot broadcast on the evening news brought back a flood of memories to two Cook County Sheriff's police officers.
"If he had been convicted like he should have been for the charges we put on him, battery to a police officer, he wouldn't have been on the street to commit those attacks," said Sgt. Kevin Farrell, Cook County Sheriff's Police.
Sergeant Farrell raced to a Schaumburg bar in 2006 after his fellow officer called for help. She was responding to a report of a fight between a bouncer and a man later identified as Heriberto Viramontes.
The officer - who works undercover now and asked her identity be concealed - said Viramontes hit her as she tried to cuff him. A year-and-a-half later, Viramontes sued the Sheriff's Office claiming he was the victim of excessive force.
"For him to sue me was like getting punched in the face again because I was the victim," said the officer.
The county settled the suit for $2,000.
A few months after Viramontes filed suit against the county, Chicago Police arrested him for drinking in public.
While in a police lock up on the Northwest Side, Viramontes claimed he was "viciously and unjustifiably assaulted and beaten" by an officer and suffered a broken wrist. Chicago Police say Viramontes was the aggressor but when the officer failed to appear in court, the charge was dropped and the city later settled a lawsuit by giving Viramontes $16,000.
Sheriff Tom Dart says people like Heriberto Viramontes and their lawyers know how to play the system.
"They say 'are you willing to risk taxpayer money on this where we can walk away from this thing for $2,000 or are you willing to roll the dice and stick taxpayers for $200,000?' And that's where it gets tricky," said Dart.
Last month Viramontes is accused of going after more money, this time a robbery with a baseball bat. One so severe it left Natasha McShane in a coma and her friend Stacey Jurich in a wheelchair.
"My first thought was if he had still been in jail, it never would have happened and those poor girls paid for it, unfortunately," said the officer.
A judge tossed the aggravated battery to a police officer charge saying the punch to the sheriff's officer could have been accidental.
As for the Chicago settlement, city lawyers say their decision to give Viramontes $16,000 was far less than the $30,000 suggested by a judge.
The attorneys who represented Viramontes in his lawsuits both declined to comment.
There is a benefit for Natasha McShane on Friday, June 4 from 5-9 p.m. at Local 399 Union Hall, 2260 S. Grove Street, Chicago. For more information, contact firstname.lastname@example.org.