His older brother, Thomas "Tommy" Kendall, told ABC7 over the phone that the 18-year-old and his girlfriend were headed to the Lil Durk concert at the United Center on Sunday night when they were robbed at gunpoint, and Jess suffered a fatal gunshot wound.
"My little brother was the best friend I had in the world, you know?" Tommy said.
Tommy is devastated that his little brother's life was cut short.
He said Jess and his girlfriend drove from Elgin into the city for the concert and parked a few blocks from the United Center.
"They're walking on the way to the concert, and four guys come, two on bikes, two on feet. They got masks on," Tommy said.
Tommy said the masked suspects took the couple's belongings and shot Jess, who later died.
Without phones, IDs or any kind of money, Jess' girlfriend managed to run and call for help. She borrowed someone's phone to tell Tommy what happened.
"Pick it up, and I hear crying. It's his girlfriend. She's like 'Tommy, Jess has been shot.'"
Two other teens were also wounded in the shooting. Tommy believes they were bystanders.
Tommy raced to his brother's bedside, but by 2:30 a.m. Monday, he said, Jess could not fight his injuries anymore.
"My mind is racing. I'm never going to see this little kid again. I did whatever I could to protect him," Tommy said. "I lost my best friend, my little brother. For what? Maybe he had $20 in his pocket."
The news of Jess' death hit his Elgin community hard.
"He cut grass in the neighborhood. He did small jobs for old people in the neighborhood. Everybody loved the kid," Tommy said.
Jess was a senior at Elgin high school, loved cars and wanted to go to automotive school.
"When you think of Jess, you think of a smart, good-looking, strong, automotive guy, you know?" Tommy said.
His older brother said they saw each other every day.
"I never thought I'd see 'Rest in peace, Jess,' posts on social media. It hits home," Tommy said.
Tommy clutched a polaroid of his little brother as he spoke with ABC7. It is a remaining, tangible connection.
"I had it in my car. I always watched over him. Now, he's watching over me. How's that supposed to work?" Tommy said.
A spokesperson for the district says counselors will be provided for anyone who needs them.
Police said so far, no one is in custody.
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