Jake Sawyer’s Story
The life of the legendary biker, bodybuilder and bad-ass

by Cliff Gallant

Editor’s note: This is the ninth installment of our serialization of Jake Sawyer’s life story. Chapter 10 will appear next month.

When I got to his apartment, Jake was raring to go, as usual. Never known him to be otherwise, actually. He’s also extremely well organized and attentive to the matter at hand, whether it’s maintaining the vintage car he recently acquired or telling his life story. When I show up for our interviews he always has pictures from the time period we’ll be discussing laid out for me to examine. On this occasion my eyes fixed immediately on a photograph taken in 1974: Jake inside Maine State Prison, giving the world the finger.

“I thought you’d go for that one!” he said with a big laugh. “The last time we spoke I told you that today we’d talk about what led to the very special moment you see pictured here, so let’s get to it!

“As you know, my friend, the late sixties and early seventies, the period following my release from San Quentin, was a very busy time for me. My paratrooper training stressed the need to hit the ground running, and that’s just what I did when I got back to Portland. Concurrent with all my other activities, though, was my involvement in a New England–wide stolen automobile and motorcycle ring, and it was that activity that led to my return to prison in the year 1974, just after I had gotten off parole.”

I looked at the floor, shaking my head in disbelief. “Why did you even get involved in that racket, Jake? Obviously you didn’t need the money, and you had to know you’d get caught sooner rather than later. You were already a convicted felon. Didn’t the probability of facing multiple counts of grand theft auto concern you at all?”

“What you have to understand, my friend, is that I didn’t have any choice in the matter,” Jake patiently explained. “I was just being who I am, right to the friggin’ core. I’ve always acted without regard for consequences. I get bored very easily, and I absolutely hate boredom, so there you go. I’d rather die than live a watered-down, average kind of life. That attitude has been both a curse and a blessing, but it’s who I am and I can’t do a thing about it. I didn’t give a rat’s ass about the money I was making. I did what I did because I was excited as hell about being in the stolen-car business, and that completely overrode any reluctance I might have had about going back to prison.”

“Oh, OK,” I said, shrugging my shoulders.

“Now that we’ve got that settled,” Jake said, “let’s get to the nitty-gritty.”

 

Dancer’s Discount Auto and Motorcycle

“My favorite thing to do was to drive my three-quarter-ton, former U.S. Mail delivery truck down to Boston and collect BMWs and high-end motorcycles from the Harvard and M.I.T. parking lots. I knew some things about the ignition switches of both kinds of vehicles, and they went very quickly on the re-sale market. I also knew their original owners didn’t care that much. Daddy would buy them another one, no problem, then he’d collect more than the vehicle was worth from his insurance company. Let’s just say there wasn’t a lot of pressure coming from the victims’ end to apprehend the culprit.

“Another form the recycled-vehicle enterprise took involved a familiar scam, but with a couple of personally developed twists. Here’s how it normally went: a guy is making payments on a vehicle he’s grown tired of, so he has someone dispose of the vehicle, reports it as stolen, collects the insurance, pays off the balance of the loan and has enough left for a good down-payment on another car.

“Well, it happened in a slightly different way with me. To begin with, instead of waiting for them to tire of their present vehicle, I’d drive up to a bunch of guys in my snappy-looking ride and look for the one who had that special glint in his eye. Then I’d take him aside and explain how we could make his present car, and the payments on it, disappear, and how he could own the gem in front of him outright, with no payments to be made, and maybe end up with a little extra cash in his pocket, to boot. When his eyes widened and his mouth dropped open, I knew he was mine. ‘Ain’t life grand!’ I’d say as I was patting him on the back.

“Another little twist involved the way I disposed of the individual’s original vehicle. The customary method in the underworld was to burn it beyond recognition, and I could very well have done that, but chose not to, just on general principles. I sometimes like to do things just to see the sparks fly, you know what I mean? There were times when I went out of my way to take unnecessary chances, just to keep myself entertained. Why the hell should I go through all the bother of hauling some damn car up to Tall Pines, Maine, and torching it in some abandoned gravel pit, for instance, when I could just push it off the end of Maine State Pier into Portland Harbor?”

“Yeah, why not?” I said. “It’s a deep ocean.”

“Well, I’ll tell you why not!” Jake yelled, laughing his head off. “Portland Harbor is tidal water, that’s why! When the ocean tide comes in, whatever’s been dumped into the water tends to get pushed down the harbor to the river. So, before long, there were a bunch of my cars down at the mouth of the Fore River, just past the bridge. Cianbro was working on a project there, and when their workers started finding cars at low tide, all hell broke loose.

“That wasn’t the only thing that drew the attention of the authorities, though. There were so many of my cars on the streets of Portland that what I was doing became common knowledge after awhile. One time I was stopped at a light in Morrill’s Corner and saw two of my cars and one of my motorcycles sitting at other lights around the intersection.

“There’s one particular transaction that kind of sticks in my mind, and I still chuckle when I think about it. It involved the owner of a very well-known and successful local business, who shall remain nameless. He was one of these guys who gets their jollies by hanging around with ruffians like me now and then. He was at the Griffin Club one night when a bunch of us were shooting our mouths off about this and that, and when I said I had a beautiful, late-model, metallic-blue Lincoln Town Car, loaded with accessories, and that I was selling it at an eighty-percent discount, the guy laughed and said he’d take it. ‘Can’t turn down a deal like that!’ he said.

“I didn’t have any further conversation with him on the matter until about a week later, when I went up to him on the street and announced that I had his new car around the corner, waiting for him. Right away his jaw dropped and he said that, gee, he was only fooling around. I told him that was just great, but that I wasn’t. That riveted him to the spot. He had no desire to be in possession of a stolen automobile, but he also knew what disrespecting me would mean, prominent businessman or not, so he ran to the bank and got my money.

“All he asked was that I drive the car to his house at night and leave it in the garage, which I did. Here’s the funny part: About ten years later a friend of his told me the guy was so paranoid about getting caught driving the car that he’d never taken it out of his garage! It’s been over forty years now and I wouldn’t be surprised if it’s still there!”

 

The Inevitable

“Well, as it happened, one fine day I was arrested on multiple charges of grand theft auto and receiving stolen property, and shortly thereafter I was put on trial. My lawyer was Dan Lilley, who is, without a doubt, the best criminal-trial lawyer anywhere, and he seems to be attracted to high-profile, long-shot cases. Everybody knew I was guilty, of course, but if anybody could get me off, Dan could.

“It took all I had to keep a straight face when the judge asked me how I pleaded and I answered, ‘not guilty.’ That’s when Dan started calling me ‘The Iceman,’ and we’ve been joking about it ever since. Hey, he had warned me that I could be facing fifty years or more, and that was enough to focus my attention.

“The upshot is that the trial ended with a hung jury. Dan put me on the stand, hoping my winning ways would carry the day, and sure enough there was an elderly black lady who took a liking to me, and she was the lone hold-out for conviction. I think she respected the fact that I didn’t rat out any of my accomplices in exchange for a lighter sentence. When Dan and I were walking by the jury box after the verdict was announced, she leaned over and put her hand on my arm and whispered, ‘Don’t you be taking folk’s nice cars and fancy motorcycles no more, son.’

“One of the most memorable things about the trial was that Henry Berry, the hard-assed district attorney who prosecuted my case, sat in his chair after the verdict was read with his head buried in his hands, sobbing his heart out. I genuinely felt bad for him. He was a decent man who had worked very hard on the case, and he desperately wanted to see justice done. That sure as hell wasn’t the way things worked out, though.

“The hung jury resulted in my avoiding the long sentence I was facing, but the D.A.’s office knew they had enough additional evidence to try me again. Dan recommended that I agree to plead guilty to lesser charges in order to avoid a second trial. So, rather than be incarcerated for the rest of my life in a federal penitentiary somewhere, I accepted a sentence of only one-to-five years in Maine State Prison.”

“Only one-to-five years?” I muttered to myself.

 

Maine State Prison

“As you might imagine, Maine State Prison was a joke to me after the other houses of incarceration I’d been in. When they found out I was a Hell’s Angel and had done time in Folsom Prison and San Quentin, even the guards looked up to me.

“All in all, I was quite content with my stay in Thomaston, Maine. There were times I missed things like my midnight runs down the Maine Turnpike on my Harley to spend time with my Hell’s Angels brothers in Lowell, or partying all night in the Old Port, of course. But I kind of relished the regularity and predictability of prison life. The wild running around and assorted criminal activities I’d been engaged in on the outside had created a sort of tension inside me, and I came to regard my stay at Maine State Prison as a kind of holistic retreat.”

I didn’t just hear that, I said to myself.

“The company at Maine State Prison was OK, for the most part,” Jake said. “At Folsom and San Quentin the inmates were mostly vicious criminals who would as soon drive a shank into your side as not, so the fellows at Maine State Prison were kind of quaint by comparison. From time to time they would shank someone, or maybe firebomb their cell, usually because the inmate ratted someone out, but that kind of thing was to be expected in any house of incarceration.

“There certainly were some characters at Maine State Prison, though. One friend of mine was so addicted to burglarizing that he became obsessed with breaking into the inmates’ canteen, just because it was the only place available to him to burglarize. He was a very small man, so he was able to squirm through the air conditioning system. When they discovered a box of Baby Ruth candy bars in his cell the next day, they knew they had their man, but he didn’t care. He had three years tacked onto his sentence, but he’d gotten his burglarizing fix.

“Another guy was in for robbing a bank in Portland, on Commercial Street, the one that had parking above it. He had a great plan, but it didn’t quite work out. Instead of bursting out of the bank and making a mad run for it, he casually walked around the corner and went up to where the parking spaces were, placed his briefcase full of money in the trunk of a car he’d left there, then got in the car and sat behind the wheel reading a newspaper, as if he was waiting for his wife to get out of work or something. He was there when the police arrived, and it never even occurred to them to check up over the bank. The whole idea was to wait until they left and then calmly drive away, but before too long he fell asleep, because he wasn’t very accustomed to reading. At the end of the day, when the bank closed, the teller who’d handed him the money was going to her car and recognized him there, slumped at the wheel with his head buried in a newspaper.

 

“So the company was interesting at Maine State Prison, but after awhile boredom started to set in and I got into various activities to keep myself amused.

“Some lifers were digging a tunnel from the prison out to the highway, and I got involved by carrying gravel I’d stuffed in my shirt out onto the prison yard and spreading it around so it wouldn’t get noticed. We were all excited because the digging was progressing well, but that ended when they ran into a solid rock ledge about ten feet short of Route 1. The guys involved didn’t much care if the authorities found out about the tunnel — they were all doing life without parole anyway — so after they hit the dead-end they summoned the warden and showed him the piece of plywood covering the entrance. The guys were so proud of their work. They became prison celebrities when a couple cement trucks showed up to fill in the tunnel, so I guess their efforts didn’t go entirely unrewarded.

“I had a hell of a good time at Maine State Prison. I know how sick that sounds, but I did. I was friggin’ stoned on weed, tripping on LSD, or drunk out of my mind most of the time, and the fun just kept coming.

“I’d always had a special talent for getting other males to do my bidding, and I had this one guard who would bring me anything he could fit into his gym bag. Drugs were the main thing I had him procure for me, of course, mainly because I rather enjoyed them myself, but also because they were the number one medium of exchange within the prison. Window-pane acid was the rage at the time. It came in dark brown squares about the size of sugar cubes, and it got so I controlled the jail population quite well by passing those little babies around.

“As for the drunk part, that’s where pruno came in. Anyone who’s done prison time knows that pruno is a homebrew made from prunes, yeast and sugar, which are smuggled out of the kitchen and made into a very smooth, great-tasting alcoholic drink. I’ve never understood why pruno has never been marketed on the outside. Maybe it’s because of the name, but it would make a million if it were prepared by the right ex-con.

“What facilitated all this hilarity for me was becoming the prison mailman. That was the most sought-after job in the prison, and almost immediately after my arrival I informed the current holder of the position that I’d be taking over for him, no questions asked. So after all the other inmates got locked up after evening chow, I was on the loose for two hours, going from cell to cell, or ‘houses,’ as we called them, delivering the inmates’ mail and a wide variety of prison contraband. I was justly compensated for my efforts by getting a piece of whatever action went down.

“Oh, yes,” Jake interjected, remembering something. “There was also my weight-lifting routine. As I’ve told you, my friend, I have long considered exercise the secret to having a happy and rewarding life. No matter what was going on with me, I’ve always fitted vigorous exercise into my schedule. The prison had a fully equipped weight room, and I was in heaven. I weighed 210 pounds and I could curl 100 pounds in each hand ten times. Anyone who knows weight-lifting knows how extraordinary that is. I got to be in the best shape of my life — and this was five years after I was runner-up in the East Coast Arm Wrestling Championships. Weight-lifting is banned in many prisons today, and I regret to say that that’s because of people like me, who actually looked forward to spending time in prison so they could engage in a regular program of bodybuilding.

“Even though I was quite content in Maine State Prison, after awhile I started thinking about getting out of there. As I’ve said, I missed spending time with my Hell’s Angels brothers down in Lowell, and I could also hear the streets of Portland calling me. Not having women in my life became kind of a drag too, if you know what I mean.”

“The thought had occurred to me,” I said, nodding and smiling.

 

Out of There

“When I began advocating for myself in earnest, it wasn’t long before my release,” Jake continued. “The first step of my plan was to request a meeting with the warden, which was granted because of my high standing in the inmate hierarchy. When I said I wanted to talk to him about an idea I had to relieve the monotony the prisoners were experiencing, and possibly ease some of the tension that was building up, he leaned forward on his desk, all ears. I’ll never forget how his face went blank, though, when I told him my idea was to order life-size, blown-up Jackie Kennedy dolls to sell to the inmates, so they’d have pleasant company in their cells and experience sexual satisfaction as well.

“As I’d anticipated, the warden thought I was absolutely out of my mind. ‘Oh, my God!’ he said, and made an appointment for me to see the prison psychiatrist. I’d always enjoyed visiting with psychiatrists because, well, we talked about me, and also because they’re so easily manipulated. I’d learned that the way to get along with psychiatric counselors was to act as though their diagnosis was spot on, and that they’d given me a new lease on life.

“The prison shrink had a masculinity complex and was very eager to impress me. At first I acted belligerent as hell towards him, just so he’d have a hill to climb, but after awhile I allowed him to think he’d won me over. Even though I insisted with great humility, and with genuine regret for my past wrongdoings, that it was important for me to pay my debt to society, and that I wasn’t sure I could be trusted on the outside, he became a committed advocate for my release.

“Those were the days when parole was granted very liberally. The criminal-justice system hadn’t yet realized that there is such a thing as a career criminal, and that setting certain ones of us free would only allow us to commit more crimes. Because of people like me, parole from prison is much harder to obtain today, and maybe I should feel guilty about that, but all that mattered to me at the time was getting out.

“I would also like to say at this time that if there are any impressionable young people out there reading this, they should not get the idea that prison is all fun and games. It isn’t. It sure as hell isn’t, and it wasn’t always that way for me either. I laugh about those days sometimes, but nobody likes being in a cell. Nobody. I had some very lonely and painful times in prison. I just made the best of a very bad situation. Better not to get in the situation in the first place, know what I mean? Just because I’m a crazy bastard doesn’t mean you have to be.”

I told Jake I admired him for saying that, and he just nodded.

“Anyway, getting back to our story, the administrative authorities at Maine State Prison were more than happy to accept the shrink’s recommendation, considering the effect I was having on the prison population, and after only nine months and eleven days away, there I was, back in Portland, eager to resume my former activities.”

 

Rested and Ready to Go

The last time we spoke, Jake mentioned that he’d done time in Lewisburg Federal Penitentiary, starting in 1977, a couple years after his release from Maine State Prison. I was very interested to know why he was sent to Lewisburg and what he experienced there.

“Well, my friend, I intended to get to that today, and yes, there’s a few things to tell, but maybe we should wait until next time. We don’t want the hard time I did at Lewisburg to get mixed up in our readers’ minds with my sojourn at Maine State Prison, know what I mean?”

I could see his point, but that led to something else we needed to discuss: how many more chapters he thought it might take to bring us up to the present. He leaned back in his chair and gave the matter a considerable amount of thought, mulling over the events of the past forty years. “Well, my friend,” he finally answered, “at the pace we’ve been going, I think we can plan on about three more chapters after this one, which would get us through the April issue of your publication. How does that sound?”

I said that sounded fine with me, and told him I was looking forward to our upcoming talks.

“Great!” he boomed. “But there’s one more thing I’d like to say to our readers at this time, if you don’t mind.”

“Sure, what is it?” I asked.

“Happy New Year!” he yelled, thrusting his fist in the air.