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HIGHWAY SAILOR: A Rollicking American Journey

When the woman Jake Massry lives with leaves him for another man because he can’t succeed as a writer, and his old world father, on his deathbed, orders him to get a “real” job, Jake, to get his head straight, hits the highways of America in his worn-out VW bus, Old Bones, in search of himself and his country.

It’s Spring 1974—prices are spiraling upward and President Nixon is embroiled in the Watergate fiasco. As he travels from place to place in Old Bones, Jake meets a colorful cast of characters: sexy women, gays, born-again Christians, philosophers, racists, bullies and Gary Morse, a 19-year-old hitchhiker who possesses a large “red ruby” given to him by a young heiress.

Excerpt Chapter 6 – “The Red Ruby”

The most striking feature in the sun-scorched Arizona desert is a tall cigar-shaped cactus that has thick stubs branching out of it and curving upwards. Saguaros—they dominated the landscape as we rolled eastward toward Phoenix.

“Hey, man,” said Gary, “wheredja get the name Old Bones for this bus?”

“One night,” I said, “I was sitting in a tavern in Eugene, Oregon. Sitting next to me was this man and his dog. The man was talking to his dog as if he were talking to a friend. And the dog listened to him as if he understood every word the man was saying. The man’s name was Stash Piatowski. What a great name—Stash Piatowski. Anyway, his dog’s name was Old Bones. And what a dog he was. He was an old, tired-out dog with coarse, wiry hair. He was a medium-sized dog that seemed so wise, loving, and gentle. I only knew those two for maybe a couple of hours, but I’ll never forget either one of them because they acted more like partners than a master and his dog. Old Bones seemed so human to me. He was just a fantastic dog is all I can say. And somewhere along the line I named this old, tired-out VW bus after him.”


Old Bones didn’t have a radio, so I was the one who broke the silence this time. “Did you ever have any bad experiences hitchhiking?”

Gary turned to me and said, “Man, think of the worst thing that kin happen to a hitchhiker.”

I thought for a second, then said, “Someone putting a gun to your head.”

“Close,” he said, “close. What happened was these two guys shot at me.”


“In Mississippi.”

“Why’d they do that?”

“I was just standin’ on the side of this road holdin’ my thumb out when I sees this car comin’ at me with a rifle barrel stickin’ outta the window. I dropped my backpack and beat it real fast into a clump of trees. Man, you never seen anyone kiss the ground like I did.”

“They actually shot at you?”

“Them motherfuckers, they shot three times. Three times, man! Then they got outta the car, one guy holdin’ a rifle and the other guy a bottle of whiskey. They looked my way and bent over laughin’, thinkin’ it was real, real funny to be shootin’ at a hitchhiker. They almost started comin’ for me when one of ‘em said, “Let’s take his backpack.” Man, was I lucky I had my ruby on me. If I didn’t, I don’t know what I woulda done. They picked up my backpack, laughin’ the whole time, and drove off. Them motherfuckers.”

With a fiery sunset behind us, we were driving toward Phoenix as the world flew by Old Bones’ windshield. Gary was lying on my bed in the back, reading his copy of Kerouac’s On the Road, or so I thought, when out of nowhere came, “I can’t find it! I can’t find it!”

“Can’t find what? What’re you talking about?”

“My red ruby!” he wailed. “I can’t find it! I had it in my right boot and now it’s not there no more!”

“You told me you sent it to your parents.”

“Naa, naa, I didn’t want you thinkin’ I had it on me.”

“Did you check all your pockets?”

“I checked everything, man.”

“Did you look in your duffel bag?”

“It was in my right boot—I don’t keep it nowheres else.” He was on the verge of tears. “That ruby was worth twenty-five hundred bucks, man.”

“How do you know?”

“’Cause I had it appraised in New Orleans.” The poor kid, he was in agony. “Hey, man, you got a flashlight in this bus?”

“Yeah. Under the bed in that black toolbox.”

While Gary was searching for his ruby, I started thinking that maybe he didn’t even have it, that maybe this was a ploy to find out what I had stashed under the bed. And what I had under there, in a brown paper bag, was $1100 in traveler’s checks.

I kept an eagle eye on him in my rearview mirror until we came to the first town along the way. It was almost dark when I pulled into a well-lit Circle K parking lot in Buckeye, Arizona. We started emptying the back of Old Bones. As soon as I saw that my traveler’s checks were there, I joined Gary in the search. We went through every inch of Old Bones and couldn’t find his precious ruby.

After reloading Old Bones, we went inside the Circle K. I bought us four sandwiches and a six-pack of beer. We had to push Old Bones before driving off into the inky desert darkness.

Poor Gary, he was heartbroken.

“Wait’ll tomorrow,” I said. “I’ll bet you anything we find it. But even if we don’t—no big deal. It’s only a piece of stone that came out of the earth. Maybe it’s back where it belongs now. Just think, if we don’t find it you won’t have to carry something that valuable with you anymore.”

Gary was too sullen to speak.

We’d driven only a few miles when I saw a sign with “State Park” on it. “What if we stay here tonight?”

“Don’t matter to me, man. Nothin’ matters no more.”

I drove in and parked off the gravel road on some soft sand. We were the only people there. We stood in the cold air listening to the sounds of the desert night. Somewhere in the distance we heard a coyote. Not far away we heard the trickling of a stream. Stars lit up the sky.

After finishing the sandwiches and guzzling down all the beer, we started getting ready for bed. I was relieving myself in the sand while Gary was taking his boots off in the bus.

“I found it!” he cried. “I found the ruby!”

“Where?” I said, zipping up my fly.

“In my left boot!”

“What a putz you are, Gary. Why didn’t you look there in the first place?”

“I coulda sworn it was in my right boot the whole time.”

“Let me see your ruby.”

It was the size of a peach pit. We whooped it up and made plans to have it appraised in Phoenix the next day.

We lay in bed, head-to-toe, but neither of us could sleep. I couldn’t sleep for many reasons. One, I didn’t want to touch Gary for fear he might think I was out for his body. Two, I couldn’t find a way to cover my freezing head without suffocating myself. And then there were thoughts, thoughts of the sweet and stubborn Maggie Brennan—Why did we break up? Was it because I couldn’t get published or because she found another man? Even though I was the one who walked out on her, was she the one who really walked out on me? There were thoughts of my lonely mother, and thoughts of my father. And Gary, he didn’t help my sleep any. He got up three times to step outside into the freezing air to piss on the desert floor.

Those were three reasons why he couldn’t sleep—plus he may have been thinking something like, “If this guy tries anything sexual, I better be ready to make sure he don’t. But why would he? Didn’t he tell me he useta live with this chick for four years?” And: “If he tries takin’ my ruby, man, I swear, I’ll kill ‘im.” And: “After he lets me off in Tucson, I hope I get me a ride all the way to Brooklyn.” And: “Man, it’s colder than a witch’s tit in this bus.”