For the second time in two years, a homeless U.S. drifter has been jailed in Sarnia then deported for illegally – and dangerously – riding freight trains over the border between Michigan and Ontario.

And this time, William Ostrander did it intentionally.

A Sarnia courtroom recently heard Ostrander, 40, was arrested by Canada Border Services Agency inland enforcement officers on June 6 outside the Exmouth Street Metro grocery store after Sarnia police officers realized he’d previously been deported. The border officers learned he jumped on a train in Battle Creek, Mich., knowing it was heading to Canada, and jumped off of it in Sarnia.

In jail since June 6, Ostrander recently pleaded guilty to two Customs Act charges, including willfully evading compliance and returning to Canada without authorization after being deported, and was sentenced to 5.5 months in jail. Border officers were waiting in the courtroom to deport him again.

Defence lawyer Robert McFadden said his client – he called him a hobo from Idaho who travels around the U.S. on trains – told him he strapped himself to a ladder between two of the train cars at the station in Battle Creek.

“Even in the car, that’s a four-hour drive,” McFadden said in the Sarnia courtroom. “It’s a lot closer to Chicago than it is to here and a very dangerous situation and I would think it would have been a very uncomfortable (ride).”

Two years ago, Ostrander, who apologized to Canada for what he did, told the court he didn’t mean to come to here, but the train he hopped on in Michigan went through an underwater tunnel heading to Sarnia and he had no choice as he couldn’t get off.

This time, though, he meant to come here.

“For some reason he likes Canada,” McFadden said.

Ostrander got two months in jail in 2022 for a guilty plea to a Customs Act charge of failing to report and was deported. The court did not hear at that time exactly how he rode the train – whether he snuck inside or was clinging to the exterior – and the prosecutor said afterward he didn’t have that information.

After emerging on the Canadian side of the St. Clair Tunnel in the summer of 2022, Ostrander lived on the streets until a Sarnia police officer came across him sitting under a tree behind a gas station during an unrelated call and he admitted who he was and how it got there.

“It was a very similar situation that day,” federal prosecutor Brian Higgins said of the latest incident.

Higgins told the judge two years ago these are fairly rare incidents.

“We don’t have a lot of these cases. I get one every few years,” he said. “I had one of these matters a number of years ago where somebody arrived on a yacht. They were watched arriving and it was a situation where they basically were being snuck into Canada.”

Ostrander was also arrested in Toronto in July 2023 and deported soon after over the Rainbow Bridge in Niagara Falls, the court heard.

Higgins told Justice Mark Poland, who imposed the suggested 5.5-month sentence, Canada is a sovereign nation that must protect its borders.

“It’s clearly planned, deliberate. He didn’t end up here by accident,” he said.

Ostrander told the judge he was denied health-care for a bad ankle injury in the U.S. and that was partly why he came to Canada.

“I apologize severely,” he said. “I did what I did.”

Poland told him it was a sad story.

“Good luck, Mr. Ostrander,” he said.

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