Prosecutors on Friday released new details about a string of attacks Chicago police have linked to a so-called “Loop Puncher,” a small group of men known for randomly attacking women in the downtown area and on the CTA. While similar unprovoked assaults have occurred for years, the cases have drawn renewed attention in recent weeks as videos of the attacks spread widely across social media.
Derek Rucker, 37, was ordered detained Friday afternoon by Judge Deidre Dyer after prosecutors outlined a series of violent incidents that investigators have tied to the 6-foot-5, 250-pound man. At least two attacks occurred this week while Rucker was on pretrial release for earlier assaults.
The most recent attack happened Thursday morning in River North, where prosecutors said Rucker walked up to a woman crossing Ohio Street near State Street around 10:30 a.m. and punched her in the side of the head without warning. The 44-year-old victim fell and struck a metal support beam as the Rucker, wearing a bright orange sweatshirt, kept walking north, then turned around and passed her again, prosecutors said.

Officers found Rucker minutes later inside the nearby CTA Red Line station at Grand Avenue, where the victim identified him as her attacker.
Investigators then linked Rucker to another assault the previous evening on a CTA Red Line train in Uptown. A 40-year-old woman told police a man matching Rucker’s description spat in her face and ear after making eye contact with her as the train approached the Wilson station. She recognized him from local news coverage of downtown attacks and reported the incident later that night.
Rucker was on pretrial release for two other physical attacks at the time of those incidents.
At about 1:15 p.m. on September 30, Rucker walked up to a 23-year-old woman on the Loyola Red Line platform and made a statement that caused her to step away, prosecutors said. Rucker allegedly raised his right hand, punched the woman in the back of the head, then sat down on a bench.
Chicago police arrested him at the scene and took him to St. Francis Hospital in Evanston for treatment of an undisclosed condition. While under police guard at the hospital, Rucker struck an officer who was standing watch over him, prosecutors said Friday.
Despite those allegations, Rucker was released from custody without appearing before a judge, a decision that allowed him to victimize more people, according to the allegations.
Investigators have also linked Rucker to another attack on the Red Line, this one around 5:30 p.m. on September 21 near the Belmont stop. Prosecutors said a 27-year-old woman had just boarded a southbound train at Addison when Rucker entered from an adjacent car and threatened to spit on her. He then allegedly followed through, spitting on her forehead before walking away. The woman recorded video of the incident and captured a photo of him as he exited onto the platform.
Shortly after Rucker’s release last week, Cook County Chief Judge Timothy Evans warned courthouse staff about him in an internal memo. The alert included Rucker’s mugshots and said Rucker had a “repeated history of punching strangers,” noting that he was “colloquially known on social media as ‘The Loop Puncher.’” The memo also cautioned that Rucker had been seen in and near court facilities.
Last week, social media accounts circulated video showing two men taunting and physically attacking Rucker because they recognized him as a “Loop Puncher.”
Young men confronts viral Chicago “Loop Puncher” who stands at 6’7” & walks around knocking out people in Chicago arrested over 20 times, A mom of 11 Kathleen Miles was knocked out cold, Northwestern University employee punched near Union Station,: Elbowed a 15-year-old girl… pic.twitter.com/I0eiRWYEn6
— Rain Drops Media (@Raindropsmedia1) October 3, 2025Rucker is also known as Derrick Davis, Derrick Rucker, and Derek Davis
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