The Poor Fortune of Winston Harrow is the first full length album from Jake Walk. It tells the story of Winston Harrow as he runs into so unfortunate circumstances involving a sinner killing villain, known as Sir Oliver, and his beautiful wife, Annabelle Lee Oliver.

The lyrics are listed below.

I've had silver and I've had gold. I've rolled dice and I've been rolled. I've sold souls and I've bet lives. I've stolen money, and guns, and wives. I've sat high on brown leather hide and I’ve ridden steeds both tame and wild. I beg for forgiveness, but I don’t regret. I’ve never been known to run from my debts.

Sir Oliver’s followers do choose to be such, their life in balance between death and his trust. His business is sinners and he scratches them out, but he'll cut you a deal if you'll join in his bout. His wife is of ivory, a bright cherished prize. Her hair is deep brown with the same colored eyes. Sir Oliver knows her to be unsoiled, but she quietly lives out her life in great spoil.

Of one bone, of only one flesh. Your knot is tied in twine of great test. But, I have found that no knot is of stone.
What’s tight becomes loose and what’s loose can be pulled. So hats off, sir trapper. For you've failed and it seems I've snared your hair. It's white fur I've matted and its long ears I've stroked bare. I'll not let go or scare. So untie, as I have myself, and brake your bonds and become flesh of mine.

In misstep I fixed up a mess of a bed. One where bedclothes were not to be smoothed. A fool! I had pounced on another man’s vamp and the bedclothes did burn just for two. I had power and clout, a gold watch at my chest, the chinking of change at my breast. I had moved mountains with lengths of blue yarn and I had blown clouds to wherever I saw fit. He'd kill me said he, but he'd grant me reprieve if I'd sought out and put out just one life.

Left handed, scarred face and black teeth. Barrel chested, with a voice of dry reeds. Nine fingers,
on one a gold ring. Lion headed with a diamond between its red teeth. Retrieve it said he and free he’ll set me,
not indebted, with my hands and sins both cleaned. Annabelle Lee, the vamp that doomed me, crimson lipped with skin of ivory. We’re crossers of borders, souls caught in a drift. Sir Oliver’s right hand with the devil’s brand burned in. So purge all sinners, there’s not a damn soul I’ll miss. Aim fast or fail and let your specter buy you simple bliss. Red he will bleed. Blue cold will I be, not remorseful, with my back to the sea. The desert awaits me, for to home I will flea—not a beggar, with no debt to plague me.

"Hey pal," I said and extended my left hand. He cracked a blackened smile, shook it, and winked hello. The lamps are turned too low, but I know—this is my ghost, this is my… So I perched high and to his right. I squinted both my eyes and asked him what he'd like. The lamps are turned too low, but I know—this is my ghost, this is my… Well, my citizen sinner, you've come to your end. You've met your dark carrier and your life I will spend to purchase my freedom, to scrape my way out. I'll not be a beggar, more years I will count. The barkeep cried and he choked back his last slug. He cracked a blackened smile, nodded, and bid farewell. Well, he thinks he walks alone but he don't—this is my ghost, this is my… So I reached right and freed my belt of its weight. Oh, I shot fast. His ring had sealed my fate. His hands to his chest and he knows he is my ghost, this is my…

I mounted and rode, my head beneath the straw. Boots dusted and spurred, face leathered and raw. The landscape was bleak, but one that I loved. Slow moving wind, low lying shrub. Well I'd done it and ran ‘cause I'd dirtied my hands. So I'll move 'til I can't, I'll be one with the sand. And with the desert my grave my sins won't be washed, my hands won't be cleaned, yet I'm forgotten by law. Her name was Old Miss, both calm and wise. Her coat was deep brown with the same colored eyes. Her muscles were mine, our choices the same. We ran from our crimes, 'cross deserts and planes.

Well excuse me sir, for I'd hate to impose, but I haven't a thread of warm enough clothes. Is it true that my death is free of charge, but my life costs some spare change and heart? It was I with the chinking of change at my breast. It was I who held time and who sold it to pests. It was I who told beggars to work like the rest. There once was a day—Now would you believe?— that I was you and some other man me. But, my shoes have worn thin with my hair and my skin. Not once had I known such poor, poor fortune. For it was I with the chinking of change at my chest! It was I who held time and who sold it to pests! It was I who told beggars to work like the rest!