A federal grand jury has indicted a 21-year-old Chicago man, accusing him of using his SUV to ram a federal immigration agent’s vehicle during an enforcement operation on the city’s Southwest Side last year.
According to federal prosecutors, Diego Emmanuel Reyes drove his SUV into the back of a U.S. Immigration and Customs Enforcement agent’s vehicle during “Operation Midway Blitz” on October 4, then continued pushing the vehicle forward.
Prosecutors released a video of the incident to the media:
Reyes faces a one-count indictment for assaulting, impeding, intimidating, and interfering with a federal officer using a deadly or dangerous weapon. This charge could lead to a maximum of 20 years in prison.
“The actions of this defendant on October 4, 2025, in Chicago, Illinois, during Operation Midway Blitz were perilous and audacious, targeting a federal agent and challenging the rule of law,” stated Andrew S. Boutros, U.S. Attorney for the Northern District of Illinois. He emphasized the commitment to prosecuting individuals who disrupt federal operations.
The ramming took place amidst heightened tensions during the operation, following a nearby shooting of a woman by a federal agent earlier that morning, which led to protests.
Footage shared on social media showed the SUV repeatedly hitting the bumper of the agent’s truck on Kedzie Avenue near 36th Place, while the truck’s emergency lights were on. Both vehicles then drove south in the oncoming traffic lane.
After passing under a viaduct, the SUV forced the Border Patrol truck into a curb at 3700 South Kedzie, raising dust from road work. Despite the crash, the SUV continued pushing the pickup, while an agent exited the truck and appeared to aim a weapon at the driver. Another federal vehicle then collided with the SUV from behind, prompting the SUV to lurch forward and come to a halt in a construction area.
Around 11:30 a.m., a CPD supervisor in the Deering (9th) District instructed dispatchers to withdraw all city police units from the shooting scene and hand over the investigation to federal authorities.
“That’s per the chief,” the supervisor stated.
“That’s per the chief of what? ICE?” a dispatcher inquired.
“Chief of patrol, squad,” replied the supervisor, referring to CPD Chief of Patrol Jon Hein.
The supervisor mentioned that one CPD unit would stay to document a traffic crash related to the incident, where a firearm was found.
“And if she needs help, we absolutely help our own, alright?” the supervisor added. “If you need resources, we’ll send you whatever you need.”
Shortly before noon, the supervisor updated dispatch: “Yeah, per the Chief of Patrol, we have all pulled out. All CPD resources are clear from the scene on California as well as Kedzie.”
Just 30 minutes later, federal agents requested CPD assistance near 39th Place and Kedzie.
A dispatcher relayed an agent’s message: “He’s one of about 30 armed Border Patrol agents, ICE. They’re being surrounded by a large crowd of people [and he is] requesting CPD. They don’t see any weapons in the crowd.”
“If you guys can immediately head down to 39th Place and Kedzie, please, and go assist them,” the dispatcher urged units leaving the station. “I’m looking on the [cameras], and there are lots of cars.”
Those CPD units responded but, per supervisory orders, stopped a couple of blocks short of where the agents said they were being surrounded. About five minutes later, they were told to leave.
“Just to confirm,” a dispatcher asked, “they were saying that they were being surrounded by that large crowd and they were requesting the police and we’re not sending?”
“Again, those are the orders we’re being given,” the supervisor replied.
The shooting marked at least the second time in a week that CPD supervisors directed officers to avoid federal enforcement actions involving ICE. Earlier, after Border Patrol agents detained a man at the scene of a West Side traffic crash, CPD officers initially responded but were later told to steer clear.
“The [crashed] car can sit in the middle of the street,” one supervisor said. “As long as we’re not over there, it’s all that matters.”
CPD Supt. Larry Snelling later denied that officers were told to stay away from federal agents in need of assistance.
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