When the judge took his seat, John Edward "Eddie" Callahan sat down softly in the defendant's chair Tuesday in U.S. District Court.

Dressed in a gray suit and brown shoes, he listened intently as prosecutors presented their case against him: Hiring homeless men on the cheap to tear asbestos out of the basement of a luxury condominium project in downtown Roanoke.

Callahan, 55, of Roanoke, pleaded guilty to a single count of violating the federal Clean Air Act in an agreement with prosecutors under which they dropped four other counts stemming from the case. He faces up to five years in prison and a fine of up to $250,000. Judge Samuel Wilson released him on bond and set sentencing for June 14.

It had been two years since an anonymous tip alerted investigators to the "rip-and-strip" job and five months since a grand jury indicted Callahan on charges that he improperly removed and dumped the hazardous material.

It's believed to be first criminal asbestos case in the Roanoke Valley, and prompted Roanoke to adopt tighter rules on removing the insulating material from the city's many old buildings.

During Tuesday's hearing, prosecutors spent nearly an hour outlining their case against Callahan. They did that with an Environmental Protection Agency investigator and a lengthy paper trail of documents and photographs displayed on an overhead projector.

The evidence showed Callahan advertised his asbestos-removal services in the Yellow Pages and the Internet, but that he had no training, certification or license to handle asbestos. He held an environmental contractor's licence for only a year, which permitted him to do pollution control and remediation work.

For five days in February 2005, Callahan hired three homeless men for $10 an hour and sent them with scant instructions into the unventilated basement on Campbell Avenue.

He dressed them in fishermen's hooded yellow rain suits, carpenters' goggles and paper masks instead of hazardous material suits, respirator masks, rubber gloves and other professional gear.

Chris Smith, the EPA investigator, testified that it was a "rip-and-strip" job that involved hacksaws tearing into the friable material -- without first wetting it down -- creating a cloud of fibers that the workers breathed in and swallowed when they ate their lunches in the basement.

The 30 trash bags of asbestos were dumped in a landfill instead of a specially designated disposal site.

Smith testified that Rob Glenn, owner of the State & City Building, and his general contractor, Cliff Mascitelli, hired Callahan for $2,100 instead of licensed asbestos contractors whose bids were about $25,000 and $13,000. Glenn later paid a licensed contractor $21,000 to finish the job properly.

Prosecutors finished by saying Callahan had followed none of the voluminous asbestos regulations in the Clean Air Act and the National Emission Standards for Hazardous Air Pollutants.

All the while, Callahan sat hunched forward in his chair, his elbows on the table, his hands clasped as if in prayer. The short, stocky man sipped water from a paper cup to quiet his bad cough. He fiddled with a gold ring on each hand, but mostly he sat still.

He had dark circles under his eyes -- he and his attorney said the accusations had left him tired and depressed. They also left him bankrupt and without a contractor's license, which was yanked for asbestos and other violations, according to court and state licensing records.

Afterward, Callahan didn't seem fazed that he faces prison time. At one point, he mentioned to his attorney that he preferred a sentencing date before late June, when he'd be on vacation.

His guilty plea done, he shook hands with the EPA agent and a prosecutor, giving them a hug and a pat on the back.

"You're just doing your job," he told them. They didn't say much in response.

Outside the courtroom, Callahan's attorney, Jack Gregory, said his client understood the seriousness of the violations and that he was "doing the right thing" by taking responsibility for his actions.

But Gregory also said federal asbestos regulations were complicated and that Callahan had made a good-faith effort to follow them. He said the workers he hired knew they were handling a dangerous material.

Callahan, who's now employed as a warehouse worker, "showed the proper remorse today," Gregory said. "It wasn't like he sent those people down there with no gear."

Asbestos, an insulating material used in construction from the 1940s to the '70s, is regulated under the Clean Air Act as a hazardous air pollutant. Studies show long-term exposure can cause life-threatening diseases, including lung cancer and asbestosis.

When the investigation started in 2005, Callahan had told The Roanoke Times he felt qualified to remove asbestos -- that he had done it on job sites for years across Southwest Virginia -- because he had watched licensed asbestos contractors doing it and had read about it in trade journals.

Assistant U.S. Attorney Jennie Waering said the government lacks the evidence necessary to bring charges on violations stemming from any earlier work Callahan performed.

Waering said she dropped the other four counts related to the State & City Building because they wouldn't have resulted in more prison time or a larger fine. The plea agreement eliminated the remote possibility that a jury would have found in Callahan's favor, she noted.

Waering wouldn't predict how much prison time Callahan would get, but she agreed with Gregory that he likely would spend some time behind bars.

"He knows he did something wrong," she said, "but it's not like he's Darth Vader."