‘Street takeover’ arrests often end with felony convictions, but not prison, court records show

Social media images from “sideshows” that occurred on November 27, 2022. (Instagram)

CHICAGO — The murder of Guillermo Caballero at a car “sideshow” in Gage Park on Sunday morning is once again shining the spotlight on street takeovers. Chicago police believe Caballero was trying to pass through an intersection that had been “taken over” but was not participating in the event when he was murdered.

The spontaneous gatherings, in which crowds block off intersections to watch drivers spin donuts in the streets, were headline news a couple of years ago. Coverage has waned as fewer incidents occur downtown, but sideshows are still nearly weekly occurrences in other neighborhoods.

We decided to look at how the justice system treated street takeover participants charged with felonies in 2022. Here’s what we learned:

About 200 cars blocked off the 4300 block of South Pulaski for a sideshow on Thanksgiving weekend in 2022. Spectators threw vehicle parts and beer bottles at police cars and then kicked CPD vehicles.

At the time, prosecutors said that Demitrian Perez, trying to escape from cops who arrived to break up the event, put his car in reverse and accelerated toward an officer at high speed. The cop moved out of the way and took shelter behind another vehicle, but Perez allegedly continued on, slamming into another occupied squad car, prosecutors claimed.

Last October, he pleaded guilty to three counts of aggravated assault of a peace officer and aggravated fleeing, according to court records. Judge Stanley Sacks sentenced him to two years of probation.

The same incident led to the arrest of Jonathan Hernandez. He was on bail for a pending gun case when prosecutors charged him with mob action, possession of a controlled substance, and aggravated assault of a peace officer at the sideshow.

He pleaded guilty to the aggravated assault charge last month in exchange for a one-year prison sentence from Judge Sacks. During the same hearing, Hernandez pleaded guilty to the gun charge, too. Sacks gave him a concurrent one-year term. He did not actually spend any time in prison because he earned credit toward his sentences while the cases were pending.

Jesus Ramos was arrested at a different sideshow the same night as Hernandez and Perez. Prosecutors said he threw asphalt at Chicago cops who responded to the street takeover at 24th and Archer. CPD said 50 to 100 cars had gathered at the intersection.

Ramos threw asphalt, according to prosecutors, which struck the sergeant’s squad car hood and bounced up onto the windshield. Ramos ran from the scene but “collided into a fixed concrete structure” and fell, a prosecutor said. The police also tased him three times.

Last week, Ramos pleaded guilty to aggravated assault of a peace officer. Judge Adrienne Davis sentenced him to one year in prison. According to the Illinois Department of Corrections, he spent no time in jail after receiving credits before pleading and receiving the state’s standard 50% sentence reduction.

On July 4, 2022, three Calumet City men were charged with arson and other serious felonies after they allegedly launched fireworks at CPD vehicles during a sideshow in the Loop. They were arrested separately near Wacker Drive and Michigan Avenue as a large crowd closed the streets so drivers could perform donuts in the intersections.

Late last year, Jiovanni Araujo and Guillermo Mota Jr. each pleaded guilty to two counts of aggravated battery of a peace officer, according to court records. Prosecutors dropped more than 30 additional felonies that each man faced. Judge Shelley Sutker-Dermer sentenced both men to 107 days time served plus two years of probation.

The third man arrested that night, Yair Cruz-Roman, continues to fight the charges.

About Tim Hecke 300 Articles
Tim Hecke is CWBChicago's managing partner. He started his career at KMOX, the legendary news radio station in St. Louis. From there, he moved on to work at stations in Minneapolis, Chicago, and New York City. Tim went on to build syndicated radio news and content services that served every one of America's 100 largest radio markets. He became CWBChicago's managing partner in 2019. His email address is tim@cwbchicago.com