Law360 Canada (July 10, 2026, 12:49 PM EDT) --

Norm Bowley

Bruce Simpson had one of those ideal clients: a recidivist with a wealthy brother who always picked up the tab. Otherwise indistinguishable from the host of vagrants who graced Number Five Court back in the day, old Bill spent the warm months variously at the Mission, the Shepherds, the Sally Ann, and in good weather, in one of Ottawa’s downtown parks.

But wintertime was a different story. The Mission, the Sheps and Sally Ann all got crowded, and a bed was not always available. But there was always a reliable backup: the regional detention centre. While alcohol was not freely available there, the beds were warm, the food was decent and old-timers like Bill were generally treated well. The bonus is that after four months of temperance, cheap wine would recover some of the kick that overuse brought about.

And so it was that as nights got longer and colder in late October, Bill did what he’d done more than once before. He launched a brick through the front window of Edelson’s Jewellers and stood there waiting for a ride to the police station. Seriously, a man has to do what a man has to do.

Bill waived everything that could be waived and shortly ended up behind the big glass wall in Number Five Court, Bruce Simpson quickly entering a guilty plea on Bill’s behalf, after which the Crown produced the criminal record.

The printout was easily an inch thick, maybe two. Not much white space. Nothing violent or morally shocking, but affronts to property real and personal throughout the Ottawa region, with occasional forays into Montreal and Toronto. Bill was a man with a taste for travel.

As is the custom, Bill carried the tome to the prisoners’ box and passed it over the glass to his client, who riffled through it a time or two, and handed it back. There was a brief conversation, after which Bruce turned to the PC Judge Matheson, a severe man of stern countenance, and advised, “Your Honour, my client can’t read. But he says that it looks about the right size.”

The place broke up, and for the first time in memory, Matheson broke into a grin, and said, “Mr. Simpson, your thoughts on sentence?”

“Your Honour, my client is well known to you and to this court. Life has not treated him well, but he presents no danger or risk to the community, except perhaps to some store windows. Given the record and the nature of the offence, my friend and I are agreed that two or three months of detention would be appropriate.”

“However,” he continued, “given the nature of winter in this city, a three-month sentence would see my client discharged some time in January. Consequently, and my friend is in agreement, we’re proposing six months’ incarceration, subject of course to statutory remission. My client would therefore be released in early spring.”

The Crown nodded agreement.

Judge Matheson turned to the prisoner and ordered him to stand. “It’s highly unusual for counsel to ask for an increase in the typical sentence, but Mr. Simpson has asked for it, and the Crown consents. Are you satisfied with that outcome?”

“Yes, Your Honour!” came the enthusiastic answer.

“Well,” responded His Honour, still smiling, “we like to have happy customers. Six months it will be.”

Justice was not only served, it was seen to be served.

In Norm Bowley’s third career, he speaks, writes and consults on matters of professional success and happiness. norm@purposeful.ca.

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