The case has put the Twin Cities in the national spotlight of senatorial politics. Craig wants to withdraw a guilty plea to misdemeanor disorderly conduct.
The offense was so minor, Minnesota law allowed him to plead guilty by mail rather than before a judge. But the case is about much more than a small infraction. Craig is fighting for his reputation and political life.
Attorney Tom Green is an expert on counseling public officials in connection with state and federal investigations. He represented Retired Maj. Gen. Richard Secorde in the Iran-Contra investigations, as well as Minnesota Sen. Dave Durenberger in the early 1990s.
Green says Craig's case is unusual among high-profile clients, because Craig chose to handle the situation himself rather than seek legal advice.
"In a typical case with someone who maintains a high profile, when they're confronting an investigation or the possibility of charges, or find themselves in the situation that the senator did, most of them would reach out for counsel before undertaking any decision on what to do. Apparently he did not do that here," says Green.
But Craig's lack of an attorney until now cuts both ways. Back in June, an undercover police officer arrested Craig for peeping into a bathroom stall and using hand and foot signals to solicit sex.
The officer offered Craig a deal -- plead guilty to a lesser charge of disorderly conduct and the officer wouldn't tell anyone about Craig's arrest. Craig went back to Idaho, and two months later he mailed in a guilty plea. Craig has now hired a high-profile lawyer and has asked to withdraw that plea.
Craig argues in court documents that he pleaded guilty to prevent the Idaho Statesman newspaper from printing articles that questioned his sexuality. University of Minnesota Law Professor Steve Simon says that argument is weak, since two months passed from his arrest to his guilty plea.
Simon says Craig's strongest argument is one that his legal brief gave only a passing glance. The plea omitted a section that asks defendants to waive the right to an attorney.
"And the criminal rules of Minnesota require specifically that when a person pleads guilty in person, or in a plea petition by mail, they be advised of that right," says Simon.
In the state's documents, the prosecutor said he told Craig to seek legal advice several times. Metropolitan Airports Commission prosecutor Christopher Renz argued that the real reason Craig wanted to withdraw his guilty plea is that he's unhappy the case went public.
At least one Idaho political scholar says in some ways, Craig may have had no choice but to try to withdraw his guilty plea. Jasper LiCalzi heads the department of political economy at Albertson College in Caldwell, Idaho. LiCalzi says a strong undercurrent in Idaho believes Craig was framed.
"There's people out to get him, the newspapers were out to get him, the national leadership was abandoning him, he should stick it out. He's done a lot of good for Idaho and we stand behind him," said LiCalzi. "And it's not miniscule. The last poll I saw in the state, 'Should he resign?' was 55-45."
A spokesperson for Craig's attorney says Craig won't attend the hearing. If the judge throws out his plea, the case will go to trial.
Attorney Tom Green says in that case, Craig would likely have to take the stand -- not because he has to, but because the press and Craig's adversaries will use his silence against him.
"Generally, the public and juries expect to see a defendant testify, even though we all know that they have the right not to," says Green. "I think that expectation becomes especially significant in the trial of a public official. And if that public official does not testify, it can cause irreparable harm, both in the courtroom and outside."
Craig has hired Washington D.C. attorney Billy Martin and Minneapolis lawyer Tom Kelly to represent him.
Martin has represented other high-profile clients including Michael Vick on dogfighting-related charges, and Atlanta Mayor Bill Campbell on racketeering, bribery and wire fraud charges.
If Porter refuses to allow Craig to withdraw his guilty plea, the senator can take it to the state's Court of Appeals, a process that likely would take several months. Oral arguments before the court are currently being scheduled about three months out, spokesman John Kostouros said.
Minnesota's appellate courts set an extremely high standard for withdrawing pleas, requiring defendants to prove that the district court abused its discretion, said Peter Knapp, a law professor at William Mitchell College of Law in St. Paul.
"Appellate courts like these decisions to rest with the district court, and they are unlikely to disturb them on appeal," Knapp said. "The road only gets tougher from here on in."
(The Associated Press contributed to this report)