A gun charge filed amid George Floyd rioting in Chicago is dismissed amid controversy

U.S. District Court records

Late one night amid the worst violence Chicago had seen in decades, prosecutors say a man who was unlawfully in the United States stood near a street corner in June 2020 and fired a gun seven times toward a passing car.

It’s not clear where the bullets wound up. But, nearly an hour later, Heriberto Carbajal-Flores pointed his gun at a second vehicle. Federal authorities say he again pulled the trigger, but this time the gun jammed.

His lawyers say he'd fired seven warning shots to defend the neighborhood but didn’t pull the trigger the second time.

But the police arrested him, and he faced state charges that included aggravated discharge of a firearm. Soon, though, those charges were replaced with a single federal charge that accused him of possessing a semi-automatic pistol — illegal because of his immigration status.

U.S. District Court records

Federal prosecutors filed the charge amid a 2020 crackdown ordered by then-President Donald Trump that was dubbed Operation Legend. Unbeknownst to them, a seismic shift in how the nation’s courts consider gun laws was on the way.

The indictment hung over Carbajal-Flores’ head until three weeks ago. That's when U.S. District Judge Sharon Johnson Coleman ruled that the law barring undocumented immigrants from possessing firearms had been applied to him unconstitutionally, wiping out the sole charge Carbajal-Flores faced for what happened in June 2020.

Since that chaotic summer, a U.S. Supreme Court decision dramatically changed the test for charges like the one lodged against Carbajal-Flores and raised new questions about bread-and-butter gun laws. It transformed legal briefs into history reports. And in Carbajal-Flores’ case, it took lawyers back in time to when colonial era gun laws required loyalty oaths from British backers and forbade the arming of Native Americans and Catholics.

“We’re looking at the time of the founding,” says Jacob Briskman, a lawyer representing Carbajal-Flores, “and whether there’s a history and tradition of disarming people of this nature.”

The Supreme Court ruling — in a case known as New York State Rifle & Pistol Association v. Bruen — said gun regulations must be “consistent with the nation’s historical tradition of firearm regulation.”

The same ruling has been used to challenge Illinois’ assault-weapons ban, leading to legal arguments about Bowie knives and Tommy guns.

Judges have shown their frustration with the high court’s mandate. A judge in Texas complained that “it sends jurists on a quixotic journey through history.” Coleman, who is Black, wrote that it requires her to rely on history and tradition from a time when she would have been regarded “as three-fifths of a person at best and property at worst.”

Pratheepan Gulasekaram, a University of Colorado law professor who's an expert on the law in the Carbajal-Flores case, says he knows of one other judge nationwide who has ruled similarly. He says Coleman’s order makes sense in light of the Bruen ruling, which he's no fan of.

Conservative commentators have criticized the Carbajal-Flores ruling and seized on the political dynamics in an election year when immigration is a hot topic. Coleman was nominated to her seat by President Barack Obama, under whom President Joe Biden was vice president.

U.S. District court records

But Coleman had refused twice before to dismiss the case against Carbajal-Flores. In the end, she threw it out because of legal developments that followed the Bruen ruling, which was handed down by six Supreme Court justices nominated by Republican presidents. Half were nominated by Trump, this year’s presumptive Republican nominee.

And Briskman notes that Coleman tailored her ruling only to Carbajal-Flores.

Defense lawyers are aggressively testing the implications of the Bruen decision, including its impact what are known as “922” gun-possession statutes. The vast majority of the challenges have been unsuccessful. Altogether, prosecutors say, judges have upheld the law that bars felons from carrying firearms more than 600 times since the Bruen decision.

A few judges in Chicago, though, have ruled otherwise, and federal prosecutors have taken the issue to the 7th U.S. Circuit Court of Appeals.

One order they’ve appealed was made by U.S. District Judge Sara Ellis, an Obama nominee. Ellis dismissed gun charges in five cases last month and wrote bluntly about the ramifications of her own ruling, saying it would “inevitably lead to more gun violence, more dead citizens and more devastated communities.”

Ellis wrote that she felt duty-bound by her “oath to uphold the Constitution — as interpreted by the Supreme Court — and thus must adhere to Bruen’s directive.” She called on the high court to reconsider Bruen, which she called a “constitutional misadventure.”

Rioting, chaos, gunshots

Carbajal-Flores pulled the trigger on June 1, 2020. Five people were killed by gunfire in Chicago that day, among 30 who were shot. Two days earlier, protests over the killing by a white Minneapolis police officer of George Floyd, a Black man, erupted into rioting and looting downtown before spreading to other Chicago neighborhoods.

Carbajal-Flores, 28 then, had come to the United States with his mother 18 years earlier, and the family settled in Little Village, according to his lawyers. He grew up there, once saved a man from a burning building in the area, is married to a U.S. citizen and “1000%” wants to become a citizen himself, according to Briskman.

But court records show he’d been charged in 13 other cases in Cook County since 2009, and arrest reports indicate he’d been affiliated with a violent street gang that has a power base in Little Village. He was once sentenced to two days in jail for reckless conduct after throwing gang signs at passing cars in the 2600 block of South Kedvale Avenue. Most of the other charges he faced were dropped.

According to his lawyers, several men used a sledgehammer on June 1, 2020, to break in to a tire store in the 3000 block of South Kostner Avenue and then took off. They say someone then organized an “impromptu neighborhood watch, including Mr. Carbajal-Flores” to prevent more looting.

His lawyers painted a picture of a chaotic night. There was gunfire. Police came and went. Police and neighborhood residents later found a stolen car, which had crashed, full of looted goods.

U.S. District Court files

That night, around 10 p.m., another neighborhood watch member handed Carbajal-Flores a gun, according to his lawyers, who say that, about a half-hour later, Chicago police officers in a white van told that group, “If you have anything, you should get it.” Carbajal-Flores' lawyers argued that he took that to mean he should arm himself with whatever weapon he could find.

Prosecutors said Carbajal-Flores admitted that he had the gun, in violation of the law, well before that interaction with police.

At 11:06 p.m., a white car drove toward the store at high speed and swerved, according to Carbajal-Flores' lawyers, who say he thought the driver had tried to hit the neighborhood watch leader, so he responded by firing seven warning shots.

At 11:41 p.m., another car drove by, and someone inside pointed a gun, so Carbajal-Flores took the gun from his pocket and pointed it at the car as it sped away, according to his lawyers.

Prosecutors say ShotSpotter technology detected the initial seven shots and that Carbajal-Flores’ actions were captured on a Chicago police camera. Besides being spotted with the gun, authorities say “he pulled the trigger repeatedly” during the encounter with the second car at 11:41 p.m., “although it appears that the gun jammed.”

Briskman says that's not true, that federal authorities told Coleman that “at no time does the video show any of the occupants in any of the passing cars brandish, point or shoot a gun at [Carbajal-Flores] or anyone on the street.”

Loyalty oaths, the Second Amendment

Carbajal-Flores’ bail was set at $5,000 on June 2, 2020, and he was released from jail the next day. After his federal indictment in September 2020, Coleman released him on an unsecured bond.

Cook County and federal court records don't show any additional charges filed against him since the fall of 2020. The state charges against Carbajal-Flores were dropped months later because of the federal charges, records show.

Briskman says the law that was used to prosecute Carbajal-Flores amounts to a broad, sweeping prohibition against any undocumented immigrant possessing firearms. In May 2021, he made his first bid to get Coleman to dismiss the case, citing Second Amendment grounds, arguing that Carbajal-Flores had acted as a member of a militia and citing his deep ties to the community.

Coleman rejected those initial efforts.

Then, less than two months after the Bruen decision in June 2022, Briskman, saying the Supreme Court had undone “over a decade of precedent rejecting Second Amendment challenges," argued that prosecutors — who had charged Carbajal-Flores with possession of a firearm while unlawfully in the United States — could not show the charge followed historical tradition.

“The federal government did not have laws restricting entry into the country until the late 19th century,” he wrote.

Prosecutors countered by noting that, in colonial times, Massachusetts and Virginia forbade the arming of Native Americans and that Virginia once prohibited Catholics from owning arms unless they swore “allegiance to the Hanoverian dynasty and to the Protestant succession."

“Similarly, during the American Revolution, colonial governments disarmed persons who refused to ‘swear an oath of allegiance to the state or the United States,’" they wrote.

Coleman, again siding with prosecutors, ruled that they’d offered examples, similar to the charge against Carbajal-Flores, of “historical limitations on noncitizens’ right to bear arms.”

Briskman tried again last August, after an appeals court decision laid out a set of guiding questions in light of the Supreme Court's Bruen ruling. The questions related to the law that bars felons from carrying firearms — but Coleman decided that nothing prevented her from applying them to the charge in Carbajal-Flores’ case.

Pointing to the historic example of British loyalists being allowed to have guns if they pledged loyalty to the American government, Coleman said she could give consideration in modern times to a single member of a group that had generally been disarmed.

She ruled that Carbajal-Flores had never been convicted of a felony, a violent crime or a crime involving the use of a weapon and that, in this case, he said “that he received and used the handgun solely for self-protection and protection of property during a time of documented civil unrest in the spring of 2020.”

There was nothing in the record to show “that he cannot be trusted to use a weapon responsibly and should be deprived of his Second Amendment right to bear arms in self-defense,” Coleman wrote, ruling that the law, as applied to him, was unconstitutional.

Gulasekaram says Coleman followed the logic of the Bruen ruling, though the law professor dismisses the Supreme Court ruling as an “intellectually bankrupt, nonsensical methodology" for determining whether a gun-possession charge is constitutional.

“What cases like Carbajal-Flores’ help demonstrate is that if you take that nonsensical methodology and apply it with any sort of rigor and consistency, you likely have to end up striking down statutes” as Coleman did, he says.

Gulasekaram, who is an expert on the federal law that prohibits non-citizens from possessing guns, says he knows of only one other federal judge — in Texas — who dismissed a gun case against an undocumented immigrant based on reasoning similar to Coleman’s.

Most judges who’ve considered such cases against immigrants have upheld the underlying laws — but Gulasekaram says those rulings are largely wrong.

“I think they’ve generally gotten away with their sloppy or cursory analyses because the subjects of regulation — unlawfully present non-citizens — are a numerically small and politically unpopular group,” he says.

Like Gulasekaram, Briskman says Coleman made the right call in light of the Bruen ruling.

“Certainly it’s given me a lot of arguments as a criminal defense attorney,” Briskman says of the Bruen decision. “And certainly it’s given me a lot of pause as a community member.”

U.S. District Court

Andrew Willinger, a Duke University law professor, says the problem with Coleman’s approach is that “it burdens courts with making fact-specific determinations in each individual case,” like when Coleman found Carbajal-Flores not to be dangerous.

The Supreme Court might clarify its thinking in a ruling expected this year in another gun case, this one involving a federal law that bans people who face domestic-violence restraining orders from having guns.

Gulasekaram says Coleman’s ruling means other non-citizens without violent backgrounds could successfully challenge their gun prosecutions.

Willinger doubts Coleman’s reasoning will catch on, though, because of the burden that case-by-case assessments would create.

Ellis, one of the judges who found the felon-in-possession law unconstitutional, identified a separate problem in her order last month. She said the Bruen ruling itself thrusts judges into a new role, one that she said she felt ill-suited to fill, that of "playing historian.”