Man with prior robbery convictions sentenced for violent CTA pedway attack

Tremaine Giles, 27, pleaded guilty to robbery and was sentenced to 6 years in prison for assaulting two women in a downtown Chicago CTA pedway.

Apr. 8, 2026 at 4:21pm

A 27-year-old man with two prior robbery convictions has been sentenced to six years in prison for a third robbery: violently attacking two women in the Jackson pedway, leaving both with concussions before fleeing with one victim's purse.

Why it matters

This case highlights the ongoing challenge of repeat offenders and the need for effective rehabilitation programs to address the root causes of violent crime in Chicago's transit system and public spaces.

The details

Prosecutors said the attack unfolded late at night as two Lakeview women, ages 22 and 25, walked through the underground pedway. Giles allegedly spread his arms to block their path, then wrapped his arms around the younger woman's chest, shoved her against a wall, and called her a derogatory name while trying to rip away her backpack. At the same time, two unknown accomplices blocked the second woman from intervening. Giles then slapped the older woman across the face, grabbed her by the hair, and threw her into a wall. He ultimately fled with the 25-year-old's purse but was unable to steal the backpack from the first victim. Both women required medical treatment and were diagnosed with concussions, with one also suffering some hearing loss.

  • The attack occurred on January 24, 2025, late at night in the Jackson pedway.
  • Giles pleaded guilty to robbery before Judge Carol Howard in 2026 and was sentenced to 6 years in prison.

The players

Tremaine Giles

A 27-year-old man with two prior robbery convictions who was sentenced to 6 years in prison for violently attacking two women in a Chicago CTA pedway.

Judge Carol Howard

The judge who presided over Giles' case and sentenced him to 6 years in prison after he pleaded guilty to robbery.

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What’s next

The judge's 6-year sentence for Giles will be reduced by half with good behavior, giving him a projected release date of May 1, 2028.

The takeaway

This violent attack in a CTA pedway by a repeat offender underscores the importance of strengthening public safety measures, improving rehabilitation programs, and addressing the systemic issues that contribute to recidivism in order to protect transit riders and make Chicago's public spaces safer for all.