On Friday, authorities unveiled new information regarding a series of violent incidents in Chicago that police attribute to a group referred to as the “Loop Puncher.” This group, consisting of several men, has gained notoriety for randomly attacking women in the downtown vicinity and on the CTA. Although similar unprovoked assaults have been a long-standing issue, recent weeks have seen these cases receiving heightened attention due to the widespread circulation of attack videos on social media.
Derek Rucker, 37, was ordered to be held in custody by Judge Deidre Dyer after prosecutors detailed a series of violent acts connected to the 6-foot-5, 250-pound man. Notably, at least two incidents occurred this past week while Rucker was out on pretrial release for previous assaults.
The latest incident occurred on Thursday in River North; prosecutors stated that Rucker approached a woman crossing Ohio Street near State Street around 10:30 a.m. and unexpectedly punched her in the side of the head. The 44-year-old victim fell and collided with a metal support beam as Rucker, clad in a striking orange sweatshirt, walked away, only to circle back and pass her again, according to court details.
Minutes later, officers apprehended Rucker inside the nearby CTA Red Line station at Grand Avenue, where the victim was able to identify him as her assailant.
Authorities have also connected Rucker to another assault that took place the night before on a CTA Red Line train in Uptown. A 40-year-old woman reported that a man resembling Rucker spat in her face and ear after they made eye contact as the train approached Wilson station. She later recognized him from news reports covering the downtown assaults and reported the encounter that same evening.
At the time of these incidents, Rucker was on pretrial release due to two other violent offenses.
On September 30, around 1:15 p.m., Rucker reportedly approached a 23-year-old woman on the Loyola Red Line platform, making comments that caused her to step back. He then allegedly raised his hand and punched her in the back of the head before sitting down on a nearby bench.
Police arrested him at the scene and transported him to St. Francis Hospital in Evanston for treatment of an undisclosed ailment. While under police supervision in the hospital, Rucker assaulted an officer who was monitoring him, according to prosecutors.
Despite these accusations, he was released from custody without a judicial hearing, a situation which prosecutors claim led to him victimizing additional individuals.
Investigators have also linked Rucker to another attack that occurred on the Red Line. This incident took place around 5:30 p.m. on September 21, near the Belmont stop, where a 27-year-old woman reported that as she boarded a southbound train at Addison, Rucker came from an adjacent car and threatened to spit at her, subsequently following through and spitting on her forehead before leaving the train. The woman managed to capture video evidence of the encounter and took a photo of him as he exited onto the platform.
Shortly after Rucker’s release last week, Cook County Chief Judge Timothy Evans issued a memo warning courthouse personnel about him. The internal alert featured Rucker’s mugshots and stated that he had a “repeated history of punching strangers,” noting his notoriety on social media as “The Loop Puncher.” The warning also mentioned that Rucker had been seen in and around court facilities.
In the past week, videos have surfaced on social media showing two men confronting and physically attacking Rucker after recognizing him as a “Loop Puncher.”
Young men confront 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, 2025
Rucker is also known by the names Derrick Davis, Derrick Rucker, and Derek Davis.
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Tim Hecke serves as the managing partner for CWBChicago. He began his career at KMOX, the iconic news radio station located in St. Louis. From there, he pursued opportunities at various stations in Minneapolis, Chicago, and New York City. Tim later established syndicated radio news and content services catering to all 100 of America’s largest radio markets. He has been with CWBChicago as managing partner since 2019.
You can contact him at tim@cwbchicago.com
