Walter David Duncan's Great American Misadventure started in Toronto, traversed southern Canada, crossed the roiling Pigeon River, clomped through thickets and woods teeming with bears and wolves, and ended up in a federal courthouse in Minneapolis Tuesday where he was sentenced to six months in jail for smuggling aliens, himself and a fellow traveler, into the country from Canada.

Some people will do just about anything to close a business deal.

At least that was Duncan's story when he got caught, sopping wet, in the back of his friend's rental car just south of the border in September. Duncan told authorities that he had a business deal in Chicago. He could not get into the U.S. legally because of his criminal background, which included international drug deals, fraud and a sexual assault.

So Duncan concocted a road trip worthy of Clark Griswold of "National Lampoon's Vacation," or Jim Carrey and Jeff Daniels of "Dumb and Dumber," only this time with a very expensive and sad twist.

As ludicrous as it now seems, court documents suggest that Duncan had successfully made the trip several times before for similar business meetings. It makes you wonder what kind of leather-tough entrepreneurs they breed up in Ontario. A pan of brownies in an office building in the U.S. can usually derail a meeting for 20 minutes. This guy's tenacious quest to make his business meeting eventually involved a U.S. attorney, the U.S. Border Patrol and the Royal Canadian Mounted Police.

As a plan, however, it was all Dudley Do Wrong.

According to court documents, Duncan persuaded two travel partners, Richard Andrew Davids and John Craig Zdybal to help him with the crazy caper. "Davids agreed to help Duncan in exchange for a free trip to Thunder Bay," documents said. Duncan sprang for a room at the Valhalla hotel and rented a silver Kia Optima: living large, but on borrowed time.

It seems clear Davids got the best of the deal.

For his free trip to Thunder Bay, his room at the Valhalla and a ride in a Kia, Zdybal instead had to accompany Duncan on his ill-conceived jump into the river and cold swim across the border. "Duncan explained he would need Zdybal's assistance crossing through the forest," court documents say. "Duncan did not want to cross the Pigeon River and surrounding woods alone for fear of being attacked by a bear or falling in the rough terrain."

I visited the High Falls about the same time Duncan made his unfortunate crossing in August. It's beautiful. But as I looked out over the surging waterfalls, I quickly realized that some crazy notions that we could build a wall to keep out scofflaws was ridiculous. Even in late summer the river was wild and the color of cola.

While Duncan and Zdybal negotiated the river, the woods, the mosquitoes and the Border Patrol, Davids drove to the Grand Portage Casino and wasted some time before going to pick up Duncan near Ryden's Border Store, where the two waited in a ditch off Hwy. 61.

Court documents say an anonymous caller snitched on the trio, and they were nabbed and arrested at a gas station just a few miles from where their international escapade had begun.

In U.S. District Court in Minneapolis Tuesday, Duncan was dressed in the requisite orange jumpsuit and he quickly apologized to the court.

"You don't have to apologize to the court, this is what I do," said U.S. District Court Judge David Doty, who suggested Duncan apologize to his family and friends instead.

"I knew it was wrong, I shouldn't have done it," said Duncan. He said his business in Canada had suffered and he may not now be able to pass it on to his son. "I basically ruined my reputation in southern Ontario and with everyone I know."

"It's hard to understand sometimes what people do," said Doty. "You probably have a hard time understanding what you did."

Assistant U.S. Attorney Clifford Wardlaw cited Duncan's crimes in Canada, the U.S. and Mexico and said that at his age, 53, "He should know better."

In closing, Duncan's attorney asked that Duncan serve the next couple of months closer to his home in Toronto, but just across the border. Doty said the Canadian would more likely be released along the North Dakota border, but plans were being made to help him get back home once he crosses back.

"The [U.S.] government is holding out its hand a little bit," Doty said.

Follow Jon on Twitter: @jontevlin