But Ron Waterman, lead counsel for the American Civil Liberties Union, is gaining confidence that his lawsuit challenging the way the state carries out its executions could end up with a positive ending for Ronald Smith.
Smith has been facing death in a small prison cell in Deer Lodge, Mont., for 30 years. He refused a plea bargain in 1983 that would have seen him avoid death row for killing two Montana men, but soon changed his mind and has been fighting his execution ever since.
He has all but run out of legal options. A request for clemency is currently before Montana's governor.
The civil liberties union filed a lawsuit in 2008 on behalf of Smith and another death row inmate. It argues that the lethal injection used in the state is cruel and unusual punishment and violates the right to human dignity.
A 2011 ruling in Montana District Court pointed to such problems as lack of training for individuals who administer the drugs and a discrepancy over whether two or three drugs should be used. Judge Jeffrey Sherlock also questioned how it's determined if an inmate is unconscious before receiving a lethal injection.
Sherlock ordered the state to change the statute governing its execution protocol.
The state is trying to bypass a requirement that it needs legislative approval to change the way it carries out executions. A hearing date was set for July but has been pushed back a year.
Waterman said Sherlock will instead be asked to simply look at the evidence and issue a summary ruling. That could happen as early as this fall.
"My prediction is the court is going to say again the only way to go forward is to fix the statute, which is what the judge said last time," said Waterman in an interview with The Canadian Press from Washington, D.C.
Waterman said the current law is "too specific." It includes a requirement that an ultra-fast-acting barbiturate be used to spare prisoners any unnecessary suffering. But sodium pentothal, which fits the criterion, is not manufactured in the United States or the European Union and cannot be imported, he said.
"The statute dictates a procedure they can't carry out and so they have to change the statute, but I don't think the statute is capable of being changed."
Waterman suggested the legislature is a house divided when it comes to the death penalty and is unlikely to agree to any changes in a vote.
He said it's very possible that Montana could retain the death penalty but not be able to proceed with any executions. That would leave the fate of death-row prisoners such as Smith in permanent limbo.
"I can live with that compromise," said Waterman, who noted it would also mean that Montana Gov. Steve Bullock wouldn't have to deal with the thorny issue.
"I would think (he) would probably be most happy to leave it in that fashion. When he was attorney general and was aware of this problem he never attempted to fix the statute."
Smith, originally from Red Deer, Alta., was convicted for shooting Harvey Madman Jr. and Thomas Running Rabbit while he was high on drugs and alcohol. He had been taking 30 to 40 hits of LSD and consuming between 12 and 18 beers a day at the time of the murders.
Smith has had a number of execution dates set and overturned.