Cadillac Man Welcomes You Into His World

Book cover for Land of the Lost Souls.

I fell into this book — fell flat on my face onto the sidewalks of New York City. Each page was a step alongside Cadillac Man as he introduced me to his friends, showed me the “street” way and relayed tales by people he had met. On occasion, he even told me a little bit about how he got where he was.  

The emotion in this book is raw. Cadillac Man’s earnestness in sharing his sorrow, joy, shame, pride, grief and love makes the book impossible to put down even as you wish you could look away. The unapologetically vivid stories and emotions are conveyed through pages of dialogue and moments when Cadillac Man directly addresses the reader.  

“There in your world, you’ve got a lot of restrictions,” Cadillac Man tells the reader, whose life situation he contrasts with the freedom of homeless life. “You need a job to stay inside, otherwise you come and join me out here. …You got to answer to somebody, right? … Not that I’m trying to glamorize homelessness, because it does have its bad points, but to me the beauty is there were no pressures.”  

Cadillac Man, Caddy to friends, is a “good man”: Honest and caring, he appreciates his street family and does what he can to protect them. It seems to be his way of atoning for what he could not provide his family before his life on the streets. He talks to these comrades in a way he could never talk to his wife. In a particularly self-aware observation during one of the closing chapters of the book, Cadillac Man posits that communication with friends and people around him might have prevented him from reaching the streets.  

“Part of the problem back then, I really didn’t have anybody to talk to besides my wife. If I had maybe one other person come over to me and say, ‘hey, you need to snap out of this shit,’ to give me one word of encouragement, maybe things would be different.” The pressure of not living up to what his wife wanted, and what he wanted to be, was one of the forces driving Cadillac Man’s move to the streets.  

His story is a lot like many we have heard and seen: he was on the right track, providing for his family, but then he got laid off from a great job unexpectedly. His subsequent jobs did not seem to be enough and they too ended, leaving him with few alternatives.  

But Cadillac Man was far from lazy. Every day on the streets he worked to take care of himself and his street family, scouring neighborhoods for recyclables and redeeming cans for cash. He even went back to working for a while before that fell apart. He confesses, “After so many disappointments, how much can you take before you break? ‘That’s it,’ I said, ‘enough is enough.’”  

Cadillac Man comes across the pages as a person who will hold you while you cry but threaten you with an ice pick if you start trouble. He is fiercely loyal and willing to sacrifice himself for the happiness of those he loves. “Word is bond,” he says, and he always follows through. A long, heartfelt chapter explores Cadillac Man’s relationship with, and mentorship of, a young girl new to the streets, and is the heart of the book.  

It shows that someone so weathered can still be gentle. He also dedicates a chapter to Old Man, who he knows is hurting and hopeless. After Cadillac Man helps Old Man get back on his feet after a bout of despair, Old Man thanks Cadillac Man and says he feels a lot better. “But his eyes were saying, ‘I want to go home, where we all want to be, to a place that will accept us for what we are, our home in the Land of Lost Souls,” Cadillac Man observes. This is not just a book about feelings. It is about the hardships and the harsh realities facing all homeless people, from abuse to mental health issues to death on freezing nights.  

The book occasionally can be confusing, as it is written in a stream-of-consciousness style and does not observe a chronological timeline, instead highlighting important times in Cadillac Man’s life. The stream-of-consciousness style suits the material, however; and despite the introduction’s warning that the reader might find misspellings or nonsensical passages, this is not the case.  

The book reads as it should –– as an honest and soul-baring account of one life that has impacted many, as we all hope our lives will do. As difficult as it can be to face the realities of homeless life presented in “Land of the Lost Souls: My Life on the Streets,” its lessons about humanity cannot be ignored.  


Cadillac Man (2009). Land of the Lost Souls: My Life on the Streets. Bloomsbury USA. 17 March 2009. ISBN 978-1- 59691-406-3 


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