News, Views, Happiness Pursued

Jake Sawyer Rides Again!

Excerpts from the explosive new memoir of Maine’s most legendary outlaw

by | Jun 27, 2021

Jake Sawyer in his lair in 2019. photos/Dave Wade


Alright, now we’ve got two books about Jake Sawyer out there — Jake: An American Original, Vol. I and Jake: An American Original, Vol. II — in addition to the 17-part series that ran in this publication’s predecessor, The Bollard (“Jake Sawyer’s Story”), and here I am still writing about him. Damn it. That’s exactly what Jake said would happen when he stopped me on the street that warm spring day nine years ago and convinced me to author his life story.

“There’s going to be at least one book, maybe two, of that I can assure you,” he’d said as we parted, having caught a flicker of doubt in my eye. “But what you have no way of knowing at the moment is that after you’ve written my life story, you’re going to go on writing about me for the rest of my life, or yours, depending on how things go. Every morning when I wake up, I’m excited as hell to find out what amazing, over-the-friggin’ top, completely unforeseen and un-sought-after adventures are in store for me that day, and that’s the way it’s going to be whether I’m eighty, ninety, or a hundred-and-four, which is what I’m aiming for. So grab your notebook and hang on tight! It’s gonna be one helluva ride!”

Don’t you hate it when someone with a huge ego turns out to be right? I walked away from that initial encounter scoffing and shaking my head, but today I’m known around town as the guy who writes the Jake Sawyer stories. Since the Bollard series ended in 2018, wherever I go, I get asked what Jake’s been up to and when the book’s coming out.

I can finally answer the second question. Jake, Vols. I and II, was published last year by Piscataqua Press. The books include all the stories and photographs from the Bollard series, along with new tales and previously unpublished photos from Jake’s adventures. We follow our hero from his wild boyhood in South Portland to Kents Hill prep school and Army paratrooper training, his days running moonshine in Kentucky and running with the Hell’s Angels in mid-’60s San Francisco, then in and out of several of the nation’s most notorious prisons, with all the outrageous hijinks in between.

A large part of Vol. II is devoted to what Jake’s been doing these past three years. As I’d been saying in answer to the first question, “Same wild Jake stuff as always — he’s still at it!” And that’s the truth. Now 83, the guy just doesn’t ever turn it off.

What kind of wild Jake stuff? you ask. Well, as usual, Jake’s been all over the place, but in choosing what to include in the books, Jake and I stuck to the standard we established at the start of this project: to make the cut, a story has to be about hot sex or brute violence, and it should be either hilarious or inspirational — preferably a mix of all four criteria. So there you go.

No spoilers here, but I can’t resist referring to a couple things. One is a picture of Jake displaying the gruesome-looking scar from a bullet wound on his upper chest. He says it’s the result of his very good friend, the one and only (and, sadly, now the late) Al Martin, firing a pistol at him, straight-on, from about 12 feet away. When you read the heartwarming story behind that shooting, I’m sure you’ll be as charmed by it as I was.  

Then there’s my account of the trip Jake and I took to the top of Mt. Washington, a harrowing ride on the narrow road that winds up the side of the peak in Jake’s very cool, customized Lincoln Town Car. The highlight of that amazing day was the grand surprise (to me, anyway) of encountering another Jonathan Sawyer at the top — he being the son I’d had no idea Jake had.

After a last-minute call from his father, Jon took a day away from his painting business, swung his leg over the seat of his Harley, and barreled halfway across Maine and up New Hampshire’s highest mountain to meet us. The conversation I had with Jon about his father that day is, to me, a standout among two books’ worth of jaw-dropping anecdotes.

Jake says he’s “over the moon” happy to finally have his life story out in hardcover. He hopes at least one thing he said or did in these stories will help someone, somewhere, face down their fears and “go for the gusto, go right straight for it,” just like he’s always done.

I asked Jake last month if he had any other news for the people, and he beamed. “Tell them that my guardian angel now has a name: Guardian Angela!” he said. “Like any other mortal might, I have had various physical afflictions from hell in the recent past, and I would likely not have survived without her kind and caring attention.

“And, get this,” Jake added. “Guardian Angela and my good friend Stanley, the owner of the Munjoy Hill Tavern, just got engaged to be married! Ain’t life grand?!”  


Excerpts from “Jake: An American Original, Vol. II”  

A story from Jake’s time in Maine State Prison circa 1974…

“One day out on the yard, I asked the warden if he would allow me to put up sign-up sheets for any convict willing to volunteer to fight for their country in the war that was going on in Vietnam. I knew he had spent twenty years in the Marines, and I also knew he respected the fact that I was an honorably discharged Paratrooper, so I assumed he would take my idea very seriously. I told him that a number of convicts were released from prison to fight in both World Wars, and they acquitted themselves very well. And we know that Maine boys make good soldiers, I told him. Just look at how Joshua Chamberlain and the 20th Maine mounted the charge at Little Round Top that led to the North winning the Battle of Gettysburg, which, of course, was the decisive battle of the Civil War.

“Actually, the warden laughed at the very idea of enlisting convicted felons in the military and sending them to Vietnam to fight the enemies of America. He thought the whole idea was completely ludicrous. But that’s not what he said after he stopped laughing. I have gone over it many times in my head and I remember exactly what he said: ‘What the hell, go ahead! Hang up all the signs you want to! Those North Viet Cong won’t know what hit ’em!’

“After the warden’s rousing words, I immediately got right into my little project. Before long, prisoners began signing up in droves to volunteer to go to Vietnam! Keep in mind that most of them were grossly out of shape, had little or no education, and couldn’t pass the physical test required to be admitted into the military. The majority of them were confirmed alcoholics or drug addicts, as well. But they got all fired up when I told them that not only would they get out of prison by signing up to fight in Vietnam, they’d also get all the alcohol and drugs they wanted, not only in Vietnam, but also when they returned home as war heroes. They were so excited that they wrote long letters home to their friends and loved ones informing them that they had decided to make amends for their wrongdoings by serving their country in combat, and if they survived they’d be coming home as heroes and free men ready to live happy and successful lives. 

“Very early one morning, at about 4 a.m., as I remember, a guard came to my cell and said he had orders to take me to the warden’s office immediately. I knew this wasn’t going to be a very good day in the ‘joint’ for Jake. When I got to his office, I saw that the warden was looking very tired and distraught. At first he didn’t even notice me standing there. He was just standing silently behind his large oak desk looking down at a pile of letters spread across it, steaming and muttering to himself. Then after a while he slowly looked up at me and said, ‘I want you to see all the anguish and alarm you’ve caused, Sawyer. These letters are from the families and friends of men in this prison who wrote home and told them that they soon would be going to war to fight for their country and might not return. Do you have any idea about the amount of hurt and confusion the people who wrote these letters are going through?’

“He went on to say he didn’t have any idea that what he had considered to be a ridiculous request by me would turn out to be such a gigantic embarrassment for him and the entire Maine State Department of Corrections. The Governor of the State of Maine had been on the line to him, he said, because the prisoners’ relatives and friends had also written to him and to their representatives in Washington looking for answers. They said things like their loved one had only robbed a gas station and didn’t deserve to die for it. He said he had no idea I had taken him seriously when he said it was okay for me to put the sign-up sheets all around the prison, and that I had misled and disillusioned the prisoners who signed up, had unnecessarily alarmed their loved ones, and had caused great harm to him personally.

“I didn’t say much in response. There was really nothing to be said. A number of prisoners, along with a couple of guards, had heard him say what he said. I wouldn’t have any problem getting first-hand witnesses to testify at any hearing board he might convene, and he knew it. Everyone present obviously knew he was joking, but, hey, the man said what he said.

“So, there was no way he could penalize me, but, needless to say, the warden and I weren’t on very good terms after that. His dim view of me was made even darker by the fact that I had become a hero to my fellow prisoners. When I told them about my visit to the warden’s office, they all cracked up big time and had me tell the story over and over. The more intelligent prisoners knew from the git-go that the whole thing was a sham, of course. Contrary to common opinion, lawbreakers are not always stupid, and those guys certainly weren’t. I’ll bet some of them are still talking about how they signed up to fight in Vietnam while they were in prison. Hey, a good story goes a long ways, you know?”    

Jake in 2019.


In the late 1990s, when the state was preparing to raze the old Maine State Prison in Thomaston and replace it with the current one in Warren, the Press Herald printed a letter from Jake:

Save Maine State Prison — reap profits

The state of Wyoming has spent millions of dollars restoring two old unused prisons because they have become two of the leading tourist attractions of that state.

Tourists spend a lot of money every year visiting those infamous prisons, and they spend it on T-shirts, coffee mugs, etc.

I am referring to the old Wyoming Territorial Prison at Laramie and the former state penitentiary at Rawlins, Wyo.

Myself and a growing number of Maine citizens are hoping that our 179-year-old prison can be saved for the same reasons that Wyoming and other states spent millions to save their historical prisons.

This very historic old prison is a potential gold mine! It’s right on Route 1.

Tear down some of the newer buildings to greatly enlarge the available parking and have fun making money.

I am trying to help save a lot of very interesting Maine history and I need a lot of help.

Get involved and help save the place where Maine’s “baddest and wildest” men did “hard time” for 179 years!

I hope that the people in charge talk to historians in Wyoming, Arizona, etc., before they make a huge mistake and destroy a valuable historic site!

Jake Sawyer
Maine State Prison
Class of ’75

The state razed the entire prison anyway.

Jake leading an exercise class for residents of his apartment building.


Shortly after Christmas in 2019, I heard that Jake had been hospitalized following a fall down a flight of stairs.

When the nurses’ station buzzed Jake to tell him he had a visitor and gave him my name, I could hear him yell back, “Who the hell is that?!”

Okay, he’s still with us, and he’s still who he was, I thought to myself, smiling and shaking my head as one of the nurses grinned and pointed me to his room.

He didn’t look pretty. It immediately struck me that in all the time I’d met with him over the past few years, I’d never seen him be anything but bubbling over with energy, clean-shaven, with his hair carefully combed, and very meticulously, even artfully, dressed. Now here he was, looking drained and troubled, unshaven, matted hair, connected up to various pieces of medical equipment, tubes coming in and out of everywhere and, somehow most alarming of all, wearing a standard-issue hospital johnny.

I knew that any kind of expression of sympathy on my part would be met with unmitigated scorn, so I said, “Well, Jake, I hope you had a good Christmas!”

“What?!” he roared. “Did you come up here to say that to me? Nurse! Come and throw this character the hell out of here!”

Not a peep from the nurses’ station, of course, each of them having become very accustomed to Mr. Sawyer’s antics by this time.

“Alright, Jake,” I drawled, “what happened? The last time I saw you we were planning to finish up a book and get it out there, and now you’re laying around in bed doing nothing. So what the hell gives? C’mon, you can tell me anything, let it all out.”

“Okay, here ya go,” he said, as if reluctantly giving in to my excessive demands. “I’ve got a confession to make. This was all my fault. Somehow or other, I got it into my head to return to my old habits for just one night, and it sure as hell turned out to be a very bad idea. I looked out my window and saw all those Christmas lights twinkling in the night, though, and I just had to be part of all that friggin’ merriment, just one more time! Just like the old days! I just had to get drunk and drugged out of mind, get into a few fights, pick up two or three babes and have an orgy, you know, here we go!”

I knew it, I said to myself.

“So, I put my best party clothes on,” he continued, “including my very cool Santa Claus hat, and went out and got drunk as hell at some wild-ass, hell-raisin’ den of iniquity that’s been the ruin of many a poor boy, now including me! The situation is that the men’s room of the establishment is located on the second floor, at the head of a very old rickety wooden staircase, and after I’d made a visit to the men’s room and was going down the stairs, some weightlifter asshole, you know how they are, was showing off for the two young women sitting at my table by shaking the friggin’ staircase with me on it, so there goes ol’ Jakie boy tumbling down the stairs and crashing at the bottom.

“As soon as I hit the floor I immediately sprung up and punched the guy’s lights out, then picked him up over my head and carried him over to the door and threw him out of it, without opening it beforehand, you understand. Picking him up and carrying him like that, then heaving him out the closed door, is evidently what caused all the damage to my ribs. Most weightlifters tend to be very heavy and awkward to handle.”

He’s still doing the same stupid stuff at eighty that he did when he was a Hell’s Angel, I sat there thinking, and I guess it showed on my face.

“No!!! No!!!” he yelled, waving his hand at me dismissively. “Don’t you know when I’m pulling your leg yet? You’ve got a long ways to go, young man!”

“Yeah, yeah, I guess I do,” I said.

“Okay, here ya go,” he said, grinning over at me and launching into the real story. “The exciting adventure in question took place on Saturday, December 21, at about nine o’clock in the morning, when I was completely sober and not feeling the effects of any recreational drugs, which is exactly the way I have been at all hours of the day, every day, for the last number of years.

“The story is simply that after finishing up [cleaning] at the Munjoy Hill Tavern that Saturday morning I drove to a good friend’s house to deliver some Christmas presents for him and his wife. We had a very pleasant gift-exchanging thing around their Christmas tree, followed by a nice brunch, but as I was going down the long flight of stairs that leads from their living quarters, with my arms full of Christmas presents and assorted goodies, I missed a step, and you see where that little piece of action got me. It was a long ways down and I hit every stair. I really couldn’t do much to help myself but, thanks to the seven-point landing technique that was drilled into me during my paratrooper training, I did manage to avoid hitting the floor head-first. I landed directly on the left side of my chest with such force that my rib cage got crushed, though, the result being three severely fractured ribs, and here we are!”

“Wow, so now you’re in a world of hurt,” I said. “I know what you’re going through. They don’t usually keep you in the hospital for fractured ribs, though, because there’s nothing they can do for you. The only thing they can do is prescribe some pain pills and send you home to heal. So what are you doing still laying around in bed, and what are all these tubes and wires and stuff all about?”

“Have I ever let you down, sir?” he asked, looking over at me in frustration. “Has any story I ever told you been boring as hell? Have any of the adventures I’ve related to you been simple [or] one-dimensional? Do you actually think that the whole story here is that I fell down a flight of stairs, fractured three ribs, and that’s it? Is that a story even worth telling?”

“Ah, no, I guess not,” I said.

“Ya, you guess not,” he scoffed. “Well, here ya go with the rest of the story. When they were assessing the damage to my ribs, a very observant young female doctor noticed something very odd about my stomach, something entirely unrelated to the ribs situation, a bulge in an odd place or something, so they did an x-ray and found that I had a seriously perforated ulcer on the lining of my stomach that was about to burst and spew poison throughout my system! If they hadn’t opened my stomach up and cut that damn perforated ulcer out, ol’ Jakie boy would have been enjoying the company of his famous ancestors in a matter of days!

“The story behind the friggin’ story, my friend, is that if I hadn’t fallen down those stairs and fractured my ribs, the friggin’ perforated ulcer wouldn’t have been discovered and I would have been gonzo. God saved my crazy ass once again! He figured he’d better find a way to get a message to me real fast, so down the damn stairs I go!”

Wow. He’s spoken of his guardian angel intervening and saving his bacon on a number of occasions, but he’d never mentioned God. I didn’t know what to make of that, so I took a deep breath and asked him point-blank if he actually meant that God had directly intervened in his life, or was he referring to his guardian angel.

He just looked over at me with a blank expression, like he didn’t really know himself why he had said “God” and not “guardian angel” the way he always had before.

Then, after a moment, he said, “Well, ah, where do you think guardian angels come from? Like, they don’t have a home, or a boss to please, or anything like that?”

I didn’t know what to say, so I just shrugged my shoulders.

On my way out I asked at the nurses’ station about Jake’s prognosis and they said it was definitely a good thing the perforated ulcer was discovered because, like Jake said, he most likely would’ve been dead in a matter of days otherwise. They also added that Jake was still a very sick man, that things could go either way in the next few days, and that even if things went as hoped, he was without question facing a long and challenging period of recovery.

“He’s going to be with us for two weeks or more before he goes to a nursing facility,” one of the nurses said, “but, don’t worry, we’ll survive!”


Not long ago, Jake sent the following letter to the editor of his local newspaper, which declined to print it:

To the Editor-

While jogging up Munjoy Hill on my way home from church last Sunday, I was looking around. It is obvious to me and many others that our beautiful city of Portland is being raped by the rich.

Our “City Fathers,” etc., are out of their minds. Ugly over-building has destroyed the quality of life in Portland.

I was born here more than eighty years ago.

What we have going on here is some Mainers selling out the majority of other Mainers that they grew up with so that they can get richer and richer.

Local developers are now looking forward to building a seven hundred car parking lot, etc., in a crowded area on the waterfront with narrow streets.

People that are destroying our way of life here deserve to have their names carved into a large, granite WALL OF SHAME!

Visualize a large granite WALL OF SHAME and a large American flag flying over Fort Gorges, coming to Portland soon.

Rev. Jonathan Parker Sawyer, Sr.
Veteran Paratrooper

P.S. Bring back the draft!

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