Jorden Morin said his mistake was agreeing to serve 60 days for assault intermittently, meaning on weekends, rather than all at once.
"I thought it was a good idea at the time," Morin, 25, said in court. "I shouldn't have taken that. It was added stress on me. I made the wrong choice."
Lawyer Albert Smelko said his client was "physically incapable" of getting himself to the Toronto-area jail.
But Judge Kevin Sherwood noted when Morin was stopped by police May 10 on his way to jail, he'd been driving the stolen vehicle for four days.
"That makes me somewhat cynical you had the vehicle just so you could get back to you intermittent sentence," Sherwood said.
He noted Morin has a lengthy criminal record with convictions for break-and-enter, possession of stolen property and breach of probation, and serves time "annually" and "semi-annually."
"It's clear from the record, you are not getting the message of deterrence," Sherwood said.
Smelko called for a six-month sentence, but the Crown pushed for a "bumped-up" sentence of 12 to 15 months, saying Morin's previous jail terms haven't been a deterrent.
If he doesn't change, Morin will "be doing a life sentence on the installment plan," Romano warned.
Sherwood sentenced Morin to 120 days for breach of probation and six months for possession of stolen property minus time served of 50 days.