FORT WORTH, Texas (AP) — A demonstrator who shot and wounded a police officer outside a Texas immigration center last July 4 was sentenced to 100 years in federal prison Tuesday, while other protesters accused of having links to antifa were given multiple decades in federal prison.

Benjamin Song was convicted of attempted murder last March after prosecutors say he opened fire and wounded a police officer at the Prairieland Detention Center in Alvarado.

The seven other protesters sentenced Tuesday received prison terms ranging from 30 to 70 years.

“Our issue with this case has always been this isn’t a bunch of terrorists. This is a bunch of kids and young adults who really have a really big heart and really wanted their voice to be heard,” Philip Hayes, Song’s attorney, said outside the federal courthouse in Fort Worth. “It was never intended that anybody get hurt. It was never intended that any shots would be fired.”

He said his client would appeal the sentencing.

“Song, aside from this day, has had an impeccable life. A former Marine. A good student,” Hayes said. “He had a lot of good qualities that were just ignored. The judge went ahead and gave as much as he could.”

One of the defendants, Daniel Sanchez Estrada, was convicted of corruptly concealing a document and conspiracy to conceal documents. Others pleaded guilty to providing material support to terrorists rather than take their case to trial.

Prosecutors say the eight are members of antifa, a decentralized anti-fascist organization that has become a target of the Trump administration. They have denied any affiliation and maintain they attended the demonstration to show support for immigrants inside the detention center.

President Donald Trump last fall signed an executive order designating antifa a domestic terrorist organization, even though there is no domestic equivalent to the State Department’s list of foreign terror organizations.

Critics warn the case could have wide-reaching impact on protests given that organizations operating within the U.S. are supposed to be protected by First Amendment free-speech rights.

Short for “anti-fascists,” antifa is not a single organization but rather an umbrella term for far-left militant groups that confront or resist neo-Nazis and white supremacists at demonstrations.

Last week, federal prosecutors charged 15 people with impeding the Trump administration’s immigration crackdown in Minnesota. They claimed the demonstrators were members of antifa who conspired against the federal government to block arrests and deportations by setting up blockades around government buildings and throwing chunks of ice at federal vehicles, among other actions.

Marcelo reported from New York.

A federal judge in Texas blocked a Biden administration rule on Monday that allowed immigration judges to indefinitely close a deportation case against immigrants on the same day Texas sued to stop the rule.

The rule, which was adopted in 2024, allowed immigration judges to close a deportation case after hearing arguments from the federal government and the immigrant in deportation proceedings, especially if the person could qualify for a benefit that allows them to stay in the country legally.

But on Monday, Texas Attorney General Ken Paxton filed a lawsuit in the Northern District of Texas in Wichita Falls to block the rule with U.S. Judge Reed O’Connor, who was appointed by former President George W. Bush.

The lawsuit against the U.S. Department of Justice was also co-filed by America First Legal Foundation, an organization founded by Stephen Miller, a senior adviser to President Trump who has focused on ways to limit both legal and illegal immigration to the country. America First Legal Foundation also previously filed various lawsuits representing Paxton against the Biden administration’s immigration policies, which helped derail President Biden’s immigration agenda in his lone term.

In this latest complaint, Paxton’s office said in the 43-page lawsuit that the Biden-era rule “effectively grant(s) indefinite amnesty to aliens illegally present in this country.”

Lawsuits usually take several months to years to settle, but in this case O’Connor ruled late on Monday in favor of Texas after the Department of Justice filed its response saying it agreed with Paxton’s office.

Paxton’s office and the DOJ did not respond to immediate requests for comment.

President Trump, in keeping with his campaign promise, has cracked down on immigrants, using many of the federal government’s resources to limit immigration and fast-track deportations, including undocumented people and others who were allowed to be in the U.S. by previous administrations.

O’Connor has been known as conservative leaders’ favorite judge because he has routinely ruled in favor of Paxton, who has strategically filed lawsuits against the Obama and Biden administration.

The fast-paced end to the rule echoes a similar maneuver conducted by the DOJ and Paxton’s office last year, when the federal agency sued Texas over a law allowing undocumented students to qualify for lower tuition rates at public universities. Hours after the suit was filed, Texas also asked Judge O’Connor to find the law unconstitutional, which he did.

After the law was overturned, legal experts said a state working with the federal government so closely for the swift overturning of a state law was unusual and raised questions about collusion.

The quick resolution to the case late on Monday was heavily criticized by immigration law experts.

“This is madness! Deliberate collusion with a federal judge to rapidly erase regulations without any input from affected parties,” said Aaron Reichlin-Melnick, a senior fellow with American Immigration Council, a group in Washington, D.C., that advocates for immigrants. “It’s clearly an unlawful act by all, and now litigants will have to seek to intervene in the already-completed lawsuit to overturn his actions.”