Three out-of-state men arrested in a Bridgeport apartment raid days before the NATO summit considered hitting President Obama’s campaign headquarters, Mayor Rahm Emanuel’s house and police stations with “incendiary devices,” according to court documents.

The trio, who are being held on $1.5 million bond apiece, are charged with conspiracy to commit terrorism, providing material support for terrorism and possession of an explosive or incendiary device. They are the first people to ever be charged with violating the state’s anti-terror statutes, which were enacted after the Sept. 11, 2001, terror attacks, authorities said.

Cook County prosecutors identified the men as Brian Church, 20, of Ft. Lauderdale, Fla., Jared Chase, 24, of Keene, N.H., and Brent Vincent Betterly, 24, of Oakland Park, Fla. According to prosecutors, the three men are self-proclaimed anarchists and members of “Black Bloc,” a band of protesters who typically mask their faces to avoid identification.

Their arrests were the result of an investigation since early May into a group suspected of making Molotov cocktails — crude bombs usually created by filling glass beer bottles with gasoline, according to court records. In documents filed by prosecutors today, authorities hinted they had audio recordings in which the defendants talked about injuring police and threatened that “after NATO, the city will never be the same.”

The men traveled from Florida to the Chicago area ahead of this weekend’s NATO meetings in order to prepare a multi-staged attack against various targets in the city, prosecutors said. According to court documents, the men planned to first attack four Chicago police stations and destroy several squad cars with “destructive devices” in order to divert the department’s attention and resources.

While authorities were distracted by those strikes, the group intended to hit Obama’s national campaign headquarters in the Prudential Building, Emanuel’s home in Ravenswood and other downtown financial institutions, prosecutors said. The group had already done reconnaissance work on the Chicago Police Department headquarters in Bronzeville in preparation for the attack, law-enforcement officials said.

The men’s attorney, Michael Deutsch, accused authorities of entrapment and suggested police targeted the men because of their anti-establishment views. The trio also was in a car that was stopped by police a week ago, leading to a YouTube video of the stop that has prompted protesters to complain Chicago police were harassing the car’s occupants.

“What we believe is that this is a way to stir up prejudice against people exercising their First Amendment rights,” Deutsch told a throng of reporters after the hearing.

Authorities singled out Church as the ringleader in court documents, saying that he wanted to recruit 16 people to conduct the raids. The recruits would be divided into four groups of four to carry out the plan, prosecutors said.

Wearing a green Army flak jacket, Church stood silently with his hands behind his back during a brief appearance today in the Criminal Courts Building. Chase also showed no reaction as prosecutors detailed the charges against him.

Betterly, with shaggy blond dreadlocks, shook his head and occasionally looked at the ceiling during the proceeding. He wore a brown leather jacket and a gray Misfits band T-shirt.

Court documents suggest the three men had been in Chicago since at least early May and were living in a three-flat in Bridgeport, a working-class neighborhood on the city’s South Side.

When police raided the apartment Wednesday evening, they recovered four completed Molotov cocktails and weapons including a mortar gun, swords, a hunting bow, throwing stars and knives with brass knuckle handles, according to law-enforcement records. They also possessed protective gear such as pre-positioned shields, assault vests and gas masks to help hide their identity during the planned attacks, prosecutors said.

Church also wanted to buy several assault rifles and indicated that if an officer pointed a gun at him, he planned to be “pointing one back,” authorities said.

Court documents indicate authorities most likely have recordings of the men discussing their plans, but the records do not indicate how the audio was obtained. Law-enforcement sources told the Tribune that police had two informants inside the Bridgeport apartment.

In the recorded conversations, the men discussed attacking other jurisdictions, planned escape routes and held late-night training sessions for engaging in combat with police, prosecutors said. They also talked about avoiding law-enforcement detection by using electronic surveillance, FBI informants and forensic evidence, according to court documents.

“The city doesn’t know what it’s in for,” an undisclosed defendant is quoted as saying in court records.

On the day of the arrests, the three men and others had detailed conversations about making “numerous” Molotov cocktails by filling empty beer bottles with gasoline and using cut bandannas for wicks, according to court records. Prosecutors said Chase purchased the gas at a nearby BP station and then returned to the flat, where the defendants donned gloves and began making the crude bombs.

Prosecutors said Chase and Church constructed the incendiary devices, while Betterly gave instructions on how to properly assemble and use them.

As they poured gasoline into the beer bottles, Church discussed the upcoming NATO summit and the role the Molotov cocktails would play, according to court documents. At one point, Church asked if the others had ever seen a “cop on fire” and discussed throwing one of the bombs into the Deering District police station in Bridgeport, prosecutors said.

After the bombs were loaded into a nearby car, police raided the apartment and arrested nine people, prosecutors said. Six were later released, leaving Church, Chase and Betterly as the only people charged in the alleged plot.

But the National Lawyers Guild, which is representing the men, scoffed at accusations of bomb making and insisted the NATO protesters simply possessed beer-making equipment.

“Charging these people who are here to peacefully protest against NATO for terrorism, when in reality the police have been terrorizing activists in Chicago, is absolutely outrageous,” said Sarah Gelsomino, a lawyer with the guild.

Church’s mother, who spoke to a reporter on the condition her name not be published, called the charges “ridiculous.”

“He would not be involved in making any kind of bombs or anything like that,” she said. “That’s just ridiculous. He knows where the boundaries are. He’s been in trouble before for stupid things, and he’s had to pay a price.”

Church’s mother said her son texted her after he and the other men were stopped by police last week, and she said she watched the video of the traffic stop. She said she agrees with other protesters who feel police harassed the men during the stop.

“So now suddenly after he’s being harassed by the police and posting it for everyone to see, now he’s being charged with terror-related stuff?” she said. “That seems kind of fishy to me.”

Church’s mother, who now lives in Florida but said she used to live in Chicago’s Irving Park neighborhood, also said she told her son to be careful if he decided to post the video of the traffic stop.

“I told him he better watch himself because (the police) will come after him,” she said.

Church is an emergency medical technician and is studying to become a paramedic, his mother said. She said she believes he and Chase lived together for a time in Florida, but she said she’d never heard of Betterly. She also said her son supports the Occupy movement and traveled to Chicago in late April to join the protests against NATO.

“He’s young and he’s impressionable and he’s very outspoken at times with his mouth, but he knows where to draw the line and not do stupid stuff,” she said.

Chase’s uncle, Michael Chase of Westmoreland, N.H., said he was shocked to learn of the charges against his nephew, who he said quit his job as a cook at a Boston restaurant in the fall to join the Occupy movement.

“He can be confrontational,” Chase said of his nephew. “If he’s pressed, he tends to lash out. I really can’t envision him doing this on his own, coming up with an idea to do something that radical.”

Chase lived in a tent for a time after joining Occupy and traveled with other members of the movement to Rhode Island, Washington, D.C., and Miami before arriving in Chicago last month, his uncle said.

“I’m not surprised that he’s in the protest movement because he’s been with it for awhile, but it’s a whole different aspect when you start talking about committing acts of terror using anything, and it’s really not his style,” Michael Chase said. “He’s had brushes with the law in the past and bumping heads with the police and so forth.

“It would not surprise me if during an arrest he was charged with resisting arrest, but it’s shocking to me that he would be charged with planning to commit an act of terror using any kind of device that would create the kind of havoc that a Molotov cocktail (would cause).”

Chase was not politically active before joining Occupy, so his decision to leave his job for the movement came as a surprise, his uncle said.

“He wasn’t involved in any of that stuff before,” his uncle said. “He complained about the economy like everybody else, but certainly he wasn’t active about doing anything about it. I was a little surprised because he obviously had to quit his job to spend time in the tent, so to speak, and I had to give him a hard time because I thought that was the wrong move.”

Michael Chase said his nephew had mentioned Church in recent phone conversations, but not Betterly.

Chase’s Facebook page, verified by his uncle, includes a link to a news story about a May Day protest in Chicago with a photo of protesters blocking the entrance to a bank in the Loop. Chase writes on the page that he is pictured in the photo.

In another post, Chase writes that the building where he was staying in Miami with other Occupy members was raided by the FBI and police. The post says he was the only person put in a police car and ends with, "(expletive) you pigs.”

Contributing: Jeremy Gorner, Becky Schlikerman, Rosemary R. Sobol