ASPEN — Charlie Sheen's plea agreement ran the risk of going up in smoke Monday when the actor learned that terms of the deal would prohibit him from smoking while performing useful public service at Theatre Aspen, a source familiar with negotiations said.

The Pitkin County jail's rules for the useful public service program, also known as community service — in which an inmate performs a task that provides a community benefit — consider it a major violation to be in “possession of smoking products, cigarette lighters and matches.”

The condition was unacceptable to Sheen and his legal team when they met with Chief Deputy District Attorney Arnold Mordkin before a 4 p.m. hearing before District Judge James Boyd. Sheen is widely described as a chain smoker.

“The whole thing hinged on his ability to smoke,” said a source who asked not to be named because the two sides agreed not to discuss publicly the ongoing talks.

It was widely anticipated that Sheen and the Pitkin County District Attorney's office were going to propose a plea agreement before Boyd.

When the attorneys in the case finally entered the courtroom at 5:30 p.m. after a lengthy delay, Mordkin told the judge more time was necessary for negotiations.

“We need more time than is available to us to [finalize] some of the finer points,” he said.

He asked the judge to vacate both the trial date and a hearing on various motions to give the sides more time to work on the agreement. Boyd agreed and asked Sheen if would waive his right to a speedy trial, a legal requirement for a trial within six months of the filing of charges. Sheen initially nodded his head, then said “yes” to the waiver when Boyd said he needed a verbal response.

Mordkin and Sheen attorney Richard Cummins didn't specify to the judge why the deal couldn't be finalized. After the hearing, Mordkin said: “It hit a snag.”

Boyd scheduled the next hearing for July 12 at 4 p.m, saying he wants the plea bargain's status to be made clear going into that hearing.

The sides thought they had a deal that would require Sheen to plead guilty to third-degree assault, a misdemeanor. In exchange, the prosecution would drop a charge of felony menacing and a misdemeanor count of criminal mischief. Sheen was arrested Christmas Day after he allegedly threatened his wife, Brooke Mueller Sheen, with a knife at the Aspen West End home where she was staying.

As part of the deal, it was proposed that Sheen would work at the nonprofit Theatre Aspen during daytime hours while he was serving his jail sentence. Sheen's legal team made the suggestion.

There were signs that something was awry in the negotiations when the 4 p.m. hearing before Boyd was delayed. Useful Public Service administrator Bev Campbell was called out of the courtroom into Mordkin's office during the delay.

A second source familiar with the negotiations, who also requested anonymity because of the sensitive nature of the talks, downplayed the fact that Sheen wouldn't be able to smoke during community service and said the plea deal evolved in an unanticipated way between Monday morning and when it was reviewed before the 4 p.m. hearing. The source said Sheen was led to believe he would be serving in the work release program, which has different, more relaxed rules than the Useful Public Service program.

The source alleged a deal for work release was agreed to by District Attorney Martin Beeson; Mordkin; Pitkin County Sheriff Bob Braudis, who oversees the jail; Jail Administrator Don Bird; Sheen and his attorneys. Questions about the deal were raised by an “underling” in the sheriff's office who felt Sheen would be instead serving Useful Public Service and that different, more stringent rules must apply, the source said.

Braudis was summoned to Mordkin's office during the negotiations and was asked to overrule Campbell's decision that Sheen would have to adhere to Useful Public Service hours if he worked for Theatre Aspen, a source said. The sheriff refused to overrule Campbell.

Under work release, a jail inmate goes to work during approved hours and essentially is a civilian, with no rules on smoking and no requirement to check in during work hours with the jail. It is typically offered to local residents who are trying to keep an established job while serving a jail sentence.

In the Useful Public Service program, there is more supervision by jail officials while the inmate is working and there is the prohibition on tobacco use, according to information on the jail's website and a copy of the Useful Public Service Release Agreement. Useful Public Service is typically above and beyond a 9-to-5-type job.

Smoking is prohibited for inmates in the Pitkin County jail.

Yale Galanter, a lawyer for Sheen and his wife, wouldn't answer a question on whether Sheen's ability to smoke cigarettes while working for Theatre Aspen affected the plea bargain.

“When I woke up this morning, I thought everything was going to be fine,” Galanter said. “It was a firm deal that was in place.”

The unspecified problem arose in last-minute talks with the prosecutor, he said. “I don't think anybody was at fault,” Galanter said.

In independent statements, Mordkin and Galanter both commented to reporters that, “Shit happens.”

Cummins held out hope that an agreement can be reached before July 12.

“We're all pushing in the same direction,” he said.

scondon@aspentimes.com