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Can Jack Get A Do-Over?

CALL HIM ON HIS CELL: He's ready, willing, but to some degree, still serving time.

TORONTO, ON — I can’t remember precisely how old I was the first time I set foot in a penal institution but I know I was in the single digits; i.e., really young.

My mom, dad, two aunts and I were in Kingston, ON., and we stopped in to see a cousin doing time for armed robbery. Many of the details are vague, but some I’ll never forget.

We had to go through a bunch of doors before we got to the visiting area.  And there was a whole lot of clanking going on.

I remember my cousin had cleaned up really well; his smooth face was shiny and shaved and his trousers looked ironed. Often, guys in jail eat healthier than they would on the streets and they often have precious little to do other than work out.

Having a cousin in prison didn’t seem like a big deal, either. 

I think that’s partly because quite a few of my pals in Sudbury had relatives in jail; but also, my late father Tom raised us with this old-fashioned philosophy; i.e., Most of those guys are a lot like you and me. What’s more, once a guy has done his time and paid his penalty, he deserves a fresh start.

My late father and his brother ran a fleet of buses. Over the years, they had all manner of day laborers and go-fers doing joe jobs. On any given day on Carter property you might have found a recent graduate of the penal system earning walkin’-around money.

If my father had actually owned such a thing as a Rolodex, it would have fallen open to “John Howard Society.”

Tom’s philosophy took root with me, too.

I sure know that if I were sentenced to jail for all the mistakes I’ve made, I’d have so much time to do I’d have to bequeath some in my will. A lot of the stuff young guys get busted for these days wasn’t even illegal when I was a kid. 

Here’s the thing.

I’ve recently made a new friend.

Let’s call him Jack.

He’s in his early 40s. He’s got two bright little kids, a wife who—like most wives—supports him way more than you might expect. He loves motorcycles, boats, electrical stuff and the doing of business.

He loves his dog.

He built an airplane once. He’s witty and articulate and he completed high school, but not much beyond. School and Jack were never friends.

Jack is a Caucasian, born-in-Canada English-speaking problem-solving type of guy. You meet guys like him at work every day.

Problem is, a few years back, he was in a business deal that went sour and he faced a long list of business-related charges. For good measure, the authorities also charged his wife.

Jack’s choice was to sit through hundreds of hours of court, paying a lawyer hundreds of dollars per hour, in the faint hope of being found not guilty—or he could take a plea bargain, which meant his wife’s charge would be dropped and he would do three years in the clink.

He—as thousands of Canadians do yearly—opted for the plea bargain. (Here’s a fact you probably didn’t know. The vast majority of time-doers have taken plea bargains. In the U.S.A., it’s upwards of 90 percent!)

Jack is now out and wants to get re-established.

If I were Tom, I’d have Jack in to sweep out the buses. If he proved reliable and hard-working and hung in there, he’d be doing something more challenging soon.

But I am not in a position to give Jack a few bucks an hour to wash the fleet.

But I do have this magazine column and would love to hear from anyone out there who might have a suggestion for the guy. He would love to drive truck.  

So. If anyone who reads this can help, contact me at

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