WHEELER DEALER: Chapter 1

It’s almost ancient history now, and most of the participants in this long-ago cops-and-robbers drama are dead and gone, most notably celebrity criminal Steve Kessler who was famous back then for engaging in a running gun battle with the forces of law and order along I84. Then after they caught him, shooting his way out of the old Rocky Butte jail.

He said they’d never take him alive, but he was wrong. And he died in prison four years ago still petitioning for the parole  he had to know he’d never get because during the escape he shot a prison guard in the head, damaging him for life. Some things you just can’t take back even if you say you’re sorry.

Which of course is what Kessler tried to do. But then, as was pointed out at one of his last parole hearings – by his old prosecutor who’d returned to make sure Kessler never got out alive – Kessler never revealed how the gun got into the prison in the first place, so what does that tell you?

Well, as it happens, I know exactly how the gun got in, and I got it straight from someone who was intimately involved in planning the escape itself – so if you’re willing the read to the end of this Substack series you’ll find out too. Useful information, I suppose, if you’re planning any jailbreaks of your own in the near future.

But more than that, it’s part of what I see as an oddly intriguing story about not just Kessler but any number of renegades, miscreants and misfits, living in another universe we really don’t know that much about. Sort of like the movie Goodfellas, but set in the seedy Portland of the 70s and 80s.

Kessler was a bad boy, that’s for sure. And so was Roger Shirley, the other main character and sometime narrator of this tale. Both graduated from the same schools of hard knocks.  MacLaren Youth Correctional Facility. In and out of Oregon State Prison plus a few other lockups along the way. Over the course of their careers both would be accused, and not always without reason, of serious acts of violence up to and including murder.

The main difference being that Kessler was into armed robbery. He actually seemed to get off on the thrill of it. And Roger was one of Portland’s foremost drug dealers. A regular wheeler dealer, if he does say so himself. Nothing he’s particularly proud of anymore, but one of the great lessons of life is that facts are facts.

Speaking of which, the last time Roger got out of OSP, which would have been in December of 1979, he and Kessler hooked up in a predictably ill-fated bank robbery cum heroin operation in Portland, and as a cover, or business front, they set up a newspaper – which as you’ve probably guessed already, was called the Wheeler Dealer. It’s offices were on the second floor of a strange triangular building at Southeast 72^nd and Sandy, right above Fairley’s Pharmacy.

So if this starts getting a little too nitty or gritty for you, what with all the robbing, shooting and illegal drug dealing going on, try thinking of it as a journalism story too.

Yes, I know, the Wheeler Dealer was only an auto trader. But as Roger would tell his staff, which on layout days numbered five or six women who typed all the ads, printed out camera-ready copy, collected the photos, then hand-rolled it all down with wax before taking it off to the printers – the  guiding principles of journalism – accuracy, honesty and fairness –still applied. As they certainly do here as well, I might add.

If it’s a ’74 Mercury with transmission problem, you can’t get away with saying it’s in mint condition. You have to make sure the right car pictures match up with the right descriptions. And for goodness sakes, get the seller’s phone number correct or you have to give them their money back.

In the interests of full disclosure, Roger acknowledges the time a rival auto trader attempted to move into the Portland market, and he put them out of business by sending over a crew one night to break into their office and cart everything away. Which, come to think of it, is the same sort of thing he used to do with rivals in the drug business. So on second thought, maybe this wasn’t that much like mainstream journalism after all. I’ve never been on the management side of things, so I really can’t say.

And I truly don’t know if they actually fooled anybody except themselves with that phony Wheeler Dealer business front because the entire law enforcement establishment – including not just the Portland Police Bureau and Multnomah County Sheriff’s Office but the FBI and DEA – was onto them from the get-go. They had them under surveillance almost from the start, and were constantly sending in informants and undercover agents to entrap them.

Which, as it turned out, is exactly what happened. So in the end, you’ll be happy to know, this is actually an uplifting story in which truth and justice prevail for once. And lucky for us, Roger Shirley, the old Wheeler Dealer himself, is here to tell us all about it.