Sal Iacono - You Cant Lose Them All
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Copyright 2021 by Sal Iacono
Foreword copyright 2021 by Jimmy Kimmel
Cover design and hand modeling by Jarrod Taylor
Cover photograph by Chris Patey (picture of boxer Fuse/Getty Images)
Cover copyright 2021 by Hachette Book Group, Inc.
Hachette Book Group supports the right to free expression and the value of copyright. The purpose of copyright is to encourage writers and artists to produce the creative works that enrich our culture.
The scanning, uploading, and distribution of this book without permission is a theft of the authors intellectual property. If you would like permission to use material from the book (other than for review purposes), please contact permissions@hbgusa.com. Thank you for your support of the authors rights.
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First edition: January 2021
Twelve is an imprint of Grand Central Publishing. The Twelve name and logo are trademarks of Hachette Book Group, Inc.
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All photos courtesy of the author.
Library of Congress Cataloging-in-Publication Data
Names: Iacono, Sal, author.
Title: You cant lose them all : Tales of a degenerate gambler and his ridiculous friends / Sal Iacono.
Description: First edition. | New York : Twelve, 2021.
Identifiers: LCCN 2020030160 | ISBN 9781538735329 (hardcover) | ISBN 9781538735343 (ebook)
Subjects: LCSH: Iacono, Sal. | GamblersUnited StatesBiography. | Television personalitiesUnited StatesBiography. | GamblingAnecdotes. | Sports bettingAnecdotes.
Classification: LCC HV6710.3 .I23 2021 | DDC 795.092 [B]dc23
LC record available at https://lccn.loc.gov/2020030160
ISBNs: 978-1-5387-3532-9 (hardcover), 978-1-5387-3534-3 (ebook)
E3-20201204-JV-NF-ORI
This book is dedicated to my sports gambling brethren who have been unable to crack the magical 52.4 percent winning threshold required to beat the house. I pray youve made up for it in drink tickets or, like me, at the buffet.
My cousin Sal (yes, he is my real cousin) is unlike anyone Ive ever known. None of us can figure out how he happened. He misses nothing. His brain is a massive supercomputer jam-packed with memories long forgotten by everyone other than him. He is a mathematical wizard. He is a physical threat, with a trunk as hard as a pigs. He has wild impulses that he elects not to control. He relishes discomfort; he rolls around in it. He is prone to sudden acts of cartoonish violence. He wrestles strangers. For years he kept his toenails long to use as weapons. He eats room service left on the floor outside the doors of hotel rooms. He gets into car accidents on purpose. Hell offer you a ride home and intentionally drive for hours in the wrong direction. Once, when I was typing, he tiptoed in and touched the center of my back with his penis.
He is a lunatic. He ate a whole basket of shrimp tails. He is a completely unpredictable, nonstop instigator of nonsense. And yet, somehow, despite a record of consistently antisocial behavior, he is everyones favorite coworker, person, and friend. The guy who randomly smashes a lamp on your desk or hangs up your phone when youve been on hold with your credit card company for forty-five minutes is the first guy you call when your mother dies (usually not his fault) or when you need a loan you know youll never have to pay back.
He deliberately threw a coworkers aunts camera in the garbage. That coworker invited him over for Christmas.
What makes Sal especially hard to figure out is his kindness, warmth, and generosity. These are qualities rarely seen in a maniac. Did I mention he is a doctor of jurisprudence? After he earned his degree at the prestigious Touro School of Law and Lawn Mowers, I convinced Sal to ditch his plan to practice real estate law and move to California to live and work with me in the lucrative world of local radio. What didnt seem like a wise decision then turned out to be one of the best decisions either of us ever made.
Sal has a totally original sense of humor. Every comment, every text, every email is a reminder that, day after day, no one is funnier. The jokes go deep. He makes you laugh all the way to your bones. The characters he surrounds himself with and cares for are almost as hard to explain as he is. To call it a motley crew would result in a lawsuit from the Motleys. They are his Island of Misfit Toys. The stories you are about to read are true. Some of the names have been changed, but no one is innocent.
Cousin Jimmy Kimmel
Hi there. Thanks for purchasing this book.
Or if youre standing in a bookstore, just thumbing through the pages, keep moving, buddy, this isnt a library.
Anyhow, in honor of Bill Belichick and the New England Patriots, I offer this cheat sheet for getting to the stories you, my adoring fans and library loiterers, want to get to. So here we go
Tony B: If I get you the phone number, will you ask her to the wedding?
Me: Sure. Go for it.
B efore we get into my stories about the seedy underworld of gambling, heres a story about how I met my wife. A risky adventure that led to the only real sure thing in my life.
Back in the spring of 1999, my friends were throwing our buddy Donick a bachelor party in Mexico. The plan was to rent a mansion in the hills of Puerto Vallarta. I didnt drink, so I would watch my pals guzzle tequila all weekend and, at the same time, pray the satellite dish would kick in so I could see the Final Four game between Duke and Michigan State.
I had very little money back then but somehow was able to bid $8,000 on Duke on credit in what is referred to as a Calcutta pool. This is where a bunch of people bid on teams and you get money for every round your squad advances in the NCAA tournament. As a result, Coach Ks team reaching the Final Four was a good thing for me.
So a bunch of us flew to Mexico for a weekend of debauchery. Puerto Vallarta is beautiful and the fellas got hammered and I was able to watch a scrambled signal of the game on satellite. Elton Brand dominated and the hated Blue Devils made the finals, which meant I was guaranteed to make money off of money I didnt have.
Isnt this a romantic story so far?
An even better call was heading out with the bachelor party later that evening to a local bar called Carlos OBrians (a name we would later bestow on our family mutt).
It was a wonderful scene. A bunch of well-to-do Hollywood dudes buying shots for the rest of the bar, which happened to be made up of mostly attractive women. My friend Daniel was handing out lemon shots; Adam Carolla was getting recognized as the host of his popular MTV show Loveline. My cousin Jimmy was there, andhaving given Adam his start in show businessthis was an ironic scenario where Adam was getting celebrity love and Jimmy wasnt. Suddenly, after a solid hour of Jimmy being ignored, a beautiful young woman in a red dress approached him.
Beautiful young woman in a red dress: Waitare you the guy on
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