Motorist dies trying to avoid Gage Park ‘takeover’ was days away from moving due to violence

After Guillermo Caballero, Jr.’s death, his father said he no longer wants to live in Chicago.

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Guillermo Caballero Jr. and his family already moved once because of increasing violence around their old home on the West Side to West Englewood on the South Side.

Early Sunday, the family was days away from moving a second time — to the south suburbs, for the same reason — when Caballero Jr., 20, was fatally shot after encountering a “street takeover” in Gage Park.

“I got a lot of bad feelings about [Chicago] because [although] it’s difficult to control it, the police aren’t doing a very good job because they cannot control the guns and crimes,” the victim’s father, Guillermo Caballero Sr., told the Sun-Times. “I don’t want to stay in Chicago no more.”

Caballero Jr. was on his way home from a party he attended to watch the Canelo Alvarez vs. Jaime Munguia boxing match when he spotted a “large gathering of drag racers” and people watching a “street takeover,” according to his father and a police report obtained by the Sun-Times.

At about 3:15 a.m. as Caballero Jr. drove east along 59th Street, he tried passing through the crowd of spectators that was blocking him at Western Avenue, when suddenly, one of the crowd members jumped on the hood of his black Honda Accord while another person stood in front of his car and fired one round through his windshield, the report said.

Caballero Jr. accelerated forward, bumping into several pedestrians at the event, when a third assailant fired more than a dozen times, again piercing the windshield and hitting him in the head, neck and arms, according to the report.

A screenshot of video posted to X that purportedly shows the moment before a gunman opened fire at a driver at a street takeover early Sunday in Gage Park.

Used with permission from Chicago Critter

Caballero Jr., who was declared dead on the scene about 3:31 a.m., died of multiple gunshot wounds, according to the Cook County medical examiner’s office, which ruled his death a homicide.

Police recovered at least 14 shell casings.

“When the police came with a report and everything, I didn’t feel so bad because I still had hope that he didn’t die,” Guillermo Caballero Sr. said of his son. “[When I saw] my son passed away, I started to cry a lot. I don’t know how to explain how I’m feeling.”

Video of the incident shared by the crime blog CWB Chicago shows a crowded intersection with dozens of cars when the shooting occurs.

“We want to see the police start doing something to find who did it,” Caballero Jr.’s father told the Sun-Times. “Whoever did it, they have to pay for it and go to jail.”

Caballero Jr. played in several soccer leagues, including some in Marquette Park on the city’s Southwest Side, and recently played on a team with his father and 14-year-old brother.

Though the young man often kept his emotions concealed and confided in his mother, Caballero Sr. saw the joy in his son’s face whenever he played soccer.

“He was very happy playing with us,” Caballero Sr. said. “His friends were very happy playing with him because he was very good.”

Caballero Jr. was tall and “very skinny” growing up, but his face “looked the same as when he was a little boy,” his father said. His family called him “Memito” since Caballero Sr., who shares the same name as his son, was already nicknamed “Memo” — a common nickname in Mexico for those named Guillermo.

At family parties, he often sang corridos, a genre of Spanish music, and songs from artist Peso Pluma whenever there was karaoke, Caballero Sr. said.

Caballero Jr. wanted to join the U.S. Army and worked at a Foot Locker in West Englewood, where his father says he thrived as a salesperson.

“For him, it was easy to sell because he can talk with the people,” Caballero Sr. said. “He [gained] a lot of customers because the people followed him.”

A GoFundMe page was created to help support Caballero Jr.’s family.

No one was in custody as of Tuesday afternoon, a spokesperson with the Chicago Police Department said.

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