The 17-year-old boy who was shot and killed on one of Uptown’s most dangerous blocks this weekend had also survived a shooting less than a block away two years ago.
Officials identified the victim as Kahlif Norwood. Police said eight males approached him as he stood in an alley behind the 5000 block of North Winthrop around 10:20 p.m. on Sunday. One of them pulled out a gun and began shooting, striking Norwood multiple times. He was pronounced dead at Illinois Masonic Hospital.
Surveillance video showed the suspects running south on Winthrop and then west on Argyle after the shooting. Police quickly shifted resources to nearby gang territories, deploying officers to Sunnyside and Magnolia to head off possible retaliation.
Norwood was also shot in Uptown on October 2, 2023, when he was 15. In that case, a gunman emerged from an alley in the 1000 block of West Argyle, near the Argyle Red Line station, and opened fire. Norwood suffered a wound to his lower leg, while a 44-year-old man was shot in the foot. No arrests were made.
Justin Peters, founder of the Chitown Crime Chasers group, said Norwood once participated in his youth mentoring program.
“Speaking from my experience, Khalif wasn’t a saint, but overall was a smart and talented kid,” Peters said. “He was like the leader of the youth group because he was the oldest, and he always gave the boys knowledge about life and the streets. He encouraged them to go down the right path.”
Peters recalled visiting Norwood in the hospital after the 2023 shooting. “I’ll never forget the night we had a long three-hour conversation about life, God, and his future plans. He wanted to get out of the streets and move on with a rapping career,” Peters said.
“This terrible news just completely shattered my heart. I feel like I failed him.”
The boy is the fifth person shot in Uptown this year and the neighborhood’s first murder victim of 2025. He is the second person shot on the 5000 block of North Winthrop this year. A 22-year-old man was shot during a robbery on April 11, just a few yards from last night’s murder. By this date last year, 10 people had been shot in Uptown, including three in the 5000 block of North Winthrop. In 2023, four people were shot during a single incident on the block.
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