When I moved to Portland in 1969, the city was on the cusp of a major transformation.

A surge of “urban renewal” would soon cut a swath across the landscape, plowing arrow straight furrows like The Franklin Street Arterial and Spring Street Expansion through meandering local streets.

Even the venerated Portland School of Fine and Applied Art (est. 1882) would eventually reimagine itself as The Maine College of Art (MECA).

Maybe it’s just my halcyon memory acting up again, but that precise moment seems to have been the “last hurrah” of a particular scruffily affable, not-quite-ready-for-prime-time assemblage of local grifters, conmen, and similarly seedy characters I’ve since come to recall fondly as “The Small Time Crooks.”

Let’s get something straight up front. There are crooks everywhere. Crooks of one sort and another have always been part of the ecosystem on this planet. Some are of the “big time” variety, others um, well, not so much. As Bob Dylan once sang: “Steal a little and they put you in jail. Steal a lot and they make you king.”

So we won’t get bogged down in a morass of moral judgments, I’ll stipulate for the record that all the crooks mentioned herein fall into Dylan’s first category.

Although I neither knew nor desired to know the sordid details of their various extra-legal enterprises, I can tell you this: Damon Runyon on his best day couldn’t have conjured up a more colorful collection of petty hoodlums than the gang who, if only in their own minds, once “ran” the streets of Portland Towne in the dark moments just before the dawn of gentrification.

Portland’s ethnic diversity back then mirrored the standard contemporary New England model. Irish, Italian, Jewish and Greek immigrants had their own neighborhoods. And, while you were never more than a few blocks from a sandwich shop named Amato’s, DiPietro’s, D’Angelo’s or Donatelli’s, there was nary pound of pickled tofu or scrap of Ethiopian cuisine to be had within a hundred mile radius of the city.

Oh, but there were certainly plenty of characters. “Cindy “ a tattooed, chain smoking, 40-something, rawhide tough bartender with a heart of gold, pulled drafts and poured well drinks six nights a week at the corner tavern where I performed on weekends. Although she’d listen to sob stories, laugh at jokes she’d heard 100 times and even run a tab for the regulars, be not deceived, Cindy was nobody’s fool.

Every spring a flock of “flimflam artists” descended on the city with the aim of bilking local merchants via a variety of underhanded methods including the infamous “change for a $20” scam. This bit of monetary slight of hand was cleverly choreographed to befuddle a busy shopkeeper just long enough for the “customer” to walk away with $25 in change from his original $20 bill.

That one worked pretty well, when it worked. Unfortunately, when conmen tried that particular con on Cindy, it didn’t work at all. They’d generally be halfway down the block before it dawned on them that she’d reverse-scammed them into pocketing $19 in change for the proffered $20. Funny thing though, I don’t recall any of ‘em storming back to complain about being “ripped off.”

Then there was the dynamic duo of Freddy “Fingers” McMann and Dan “Deck ‘Em” Donatello.

Having done “hard time” in Thomaston for breaking and entering and safe-cracking, it probably made sense that upon his release, McMann opened a locksmith shop on Congress Street.

The shop was a magnet for shady characters, and it wasn’t too long before “Fingers” partnered up with Donatello, a successful and charismatic local heavyweight boxer with a flair for publicity and impeccable criminal credentials to go along with his Golden Gloves title.

Shortly after he’d captured even more local headlines than usual for his involvement in a “steal ‘em in Boston, sell ‘em in Portland” car theft ring masterminded by McMann, I spotted the out-on-bail Donatello cruising Congress Street in a brand new El Dorado convertible.

Flashing his patented thousand-watt smile and pointing to a strip of duct tape covering a rather obvious knife slice in the canvas top above the driver’s door, he yelled, “Where do you think I got my new Caddy?”

Laughing gleefully, he hit the gas, laid twin strips of rubber and headed out of town.

I haven’t seen or heard of him in 40 years. Like “Fingers” McCann, Cindy the bartender and the rest of The Small Time Crooks, Donatello may be gone, but he’ll never be forgotten.

Author’s note: This column refers to actual people and real events. The names have been changed to protect the guilty.