One of the serial attackers who has punched women across the city of Chicago was in court Friday facing six felony charges in five attacks over the past few weeks.

Derek Rucker,  37, has a long rap sheet. There are questions about why more wasn't done by authorities to prevent the attacks.

The five attacks Rucker appeared in court for Friday took place over the past three weeks. He faces six felony charges for aggravated batteries against women and a police officer. His most recent arrest came Thursday on State Street after Chicago police said he struck a 44-year-old woman in the face.

Police said Rucker has also assaulted a Chicago police officer, punched a woman in the face with a closed first , spit on a woman and punched a woman in the back of the head on a CTA platform.

Video posted on TikTok and obtained by the Chicago Tribune shows police arresting Rucker in the incident on the train platform.

His criminal history, which dates back to 2006, is comprised of mostly misdemeanors, and charges ranging from battery and assault to trespassing and theft.

CBS News Chicago Legal Analyst Irv Miller pointed out that when he was charged with yet another misdemeanor in November 2024, police and prosecutors knew he'd been arrested at least 39 times.

The police report in that case details Rucker spitting on the officer arresting him after he assaulted a 62-year-old man with a belt and stick, cutting his head. Police said, at the time, they charged him with a misdemeanor because they couldn't reach his victim.

When CBS News Chicago asked Chicago police about that, they reiterated they couldn't reach the victim. But Miller sees a discrepancy.

"The problem with that is he was arrested at 1 o'clock in the afternoon and they approved the misdemeanor charge at 6 o'clock at night and that's not really a lot of time to look for somebody who's the victim of a serious crime," he said.

Rucker was also on felony probation at the time for assaulting a nurse in the hospital months before.

"I think the Chicago police detective had the obligation to notify the State's Attorney in this case and seek felony charges. It wasn't done," said Miller. "If he would've been charge with a felony involving the case with the 62-year-old gentleman I have no doubt he would have been detained pending trial in the Cook County Jail, and he would not have been on the streets, so it never would've happened." 

Rucker was ordered held remanded into custody at his court hearing Friday and will remain in Cook County Jail until his trial, the Cook County Sheriff's Office said. 

CBS News Chicago reached out to the Cook County State's Attorney to ask why more hadn't been done to keep a repeat offender off the streets.

A spokesperson declined to comment on the specifics of prior cases, but said prosecutors evaluate "each case based on the available evidence and the applicable law."

"When appropriate, the CCSAO seeks pre-trial detention for individuals who pose a danger to the community as was done in this case. We take our role very seriously in presenting the fullest possible picture for judges, who ultimately make detention decisions. Our office reviews all cases for felony approval when presented by law enforcement and maintains a continuing obligation to assess the evidence in every charged case. Our priority remains ensuring fairness, accountability, and the safety of the communities we serve," the state's attorney's office added.