You Can't Lose Them All: Tales of a Degenerate Gambler and His Ridiculous Friends

by Sal Iacono, Jimmy Kimmel (Foreword)

In this informative and entertaining book, learn from Cousin Sal how not to gamble your life away -- along with many other life lessons -- so you don't have to learn the hard way.

Over the last forty years, Cousin Sal has made bets with doctors, lawyers, teachers, agents, bookies, writers, comedians, radio DJs, tv producers, baseball players, front office executives, bandleaders, movie stars, publicists, weed lab owners, hedge fund operators, and even professional wrestlers. From his early days growing up in Brooklyn and Long Island flipping baseball cards to now hosting podcasts and TV shows and managing several offshore accounts we don't talk about, Cousin Sal has truly become the average American sports fan's go to source for gambling tips.

So here's how not to do it . . .


With hilarious tales of love and loss, winning and (a lot) of losing, crazy family and fatherhood, and a life saga that inspired the Phil Collins' song, "Against All Odds," Cousin Sal has now written THE Vegas super-system, MIT-algorithmic, sharp-approved book for how to gamble like a pro -- or at least not how not to go broke and lose your kids to Child Protective Services.

Genres: Sports, Nonfiction, Biography, Audiobook, Memoir

256 pages, Hardcover

Published January 26, 2021

Reviews

[Ben · Rating 5 out of 5]

Good job by you Sal

[Zack Teibloom · Rating 3 out of 5]

I love Cousin Sal so I had fun with hearing his best stories, but I only recommend this book to those who know and enjoy him already. After listening to him every Monday for a decade on Simmons’ podcast I knew a lot of these stories already, but had fun hearing them all collected here. It’s nothing special writing wise, but he gets in and out of all his gambling stories and it’s worth the quick read if you like him. 4 stars for fans, 2 stars for non fans.

[Mike Schaefer · Rating 3 out of 5]

Let’s start with the fact I love Cousin Sal’s persona during his podcasts, television appearances and Twitter. He’s impressively quick witted, he’s perfected his timing and he’s got the appealing quality of being someone you think you’d be friends with even though you’ll never meet.

I was excited for this book. I was even more excited when I learned he was reading his own audiobook.

And it’s what I expected. Some funny new stories, some funny old stories, a wide cast of characters and a chance to let us in a little more about his unexpected but deserved rise to fame.

I suppose, through no fault of Sal’s, because it was what I sort of expected and because I’ve already consumed so much Cousin Sal content, it all felt a little flat for me. There didn’t feel like a lot of new ground. Or maybe a book about gambling stories can’t really break beyond a certain level.

Nevertheless, I’m glad I bought it and listened, but I’d be lying if I said I was hoping there’d be a little more.

[Ian Holmquist · Rating 4 out of 5]

After listening to “Cousin” Sal Iacono rave about his terrible bets for years on The Bill Simmons Podcast, I felt justified in purchasing his book as a form of therapy. As someone who has experienced countless bad gambling beats, I figured that reading about someone else’s poor luck may offer some solitude. Within the first few pages, I found myself laughing out of shock and dismay after learning how deep Sal has dived into the bottomless well of wagering.

Throughout the book, Sal does an excellent job at bringing his stories to life. While podcast listeners or Jimmy Kimmel Live viewers may know some of these tales already, Sal has an uncanny ability to coherently introduce the wide variety of characters in his life without overwhelming the reader. I quickly found myself engrossed in each of his stories, which are normally isolated within 5-10 paged chapters. This sometimes leads to a lack of cohesive flow between certain stories, but I still found myself looking forward to reading what wacky thing Sal was going to say next.

This book is perfect for anyone looking for a lighthearted, quick read, although I found myself slowly working through a chapter or two a night: it was a perfect way to wind down and have a laugh before calling it a day. Although the subject matter focuses heavily on sports gambling, I think many people would still find a lot of fun within this book. Lots of celebrity tie-in’s helps to connect with readers who could care less about the winner of the San Jose State vs. UNLV game.

In many ways, You Can’t Lose Them All is a look into my future. I am bound for a lifelong pain and suffering as I continue to gamble. I pray that I can only gain half of the hilarious stories that Sal has through this hobby for losers and degenerates.

[Mike · Rating 4 out of 5]

As a frequent listener to Cousin Sal on various podcasts, I had hears most of the stories told in the book, but that didn't make them less funny or crazy. If you've spent a lifetime involved with fantasy sports and sports gambling, this is a must read as we all have some stories somewhat like this, but when you happen to be Jimmy Kimmel's cousin, instead of stories of your friend Bob, it's about Tony Romo or the time you ended up in a WWE match. Sal did a good job of mixing in his family into both how he became the degenerate he is but also how his wife and kids keep him from going overboard.

Definitely entertaining and I have to think if most of the stories are new to you, will lead to some laugh out loud moments.

[Joe Tuohey · Rating 1 out of 5]

Let me say this: I generally enjoy Cousin Sal. It’s why I bought this book. But quite honestly, this book is atrocious. The writing style is rough, the stories are pretty ho-hum, and he makes several questionable political statements in passing. A waste of time.

[Graham Hill · Rating 3 out of 5]

If you’ve listened to any podcasts he is on these are just recycled stories mainly.

[Kevin O'Donnell · Rating 4 out of 5]

Sal's stories are hilarious. Funny read it's not about getting knocked down it's about getting back up!

[Nate Bringhurst · Rating 2 out of 5]

I love Sal, but this was on the boring side. One extra star for hearing a Cowboy fan admit Emmitt Smith is overrated and an awful human being.

[Eric Punt · Rating 3 out of 5]

Good stories and Sal makes good jokes for a nice easy read. The only problem as a long time listener to his Guess the Lines Podcast I’ve heard most of them.

[RICK "SHAQ" GOLDSTEIN · Rating 2 out of 5]

RICK “SHAQ” GOLDSTEIN SAYS: BELOW LOWBROW… “ALMOST HUMORLESS”!
-----------------------------------------------------------------------------
This “book”… I guess I have to call it a book… because it has a front and back cover… it has pages in between the covers… and there are words printed on the aforementioned pages.

But…

Right from the very beginning of the book… in fact right at the table of contents… you know things are probably going to be bad. (In fact… Santa agreed and put in on “His-Bad-List”!) The table of contents is printed with extremely light white dotted characters… (and now imagine this) on a dark bland black background… and now where it gets unbelievably worse… under the chapter title… in even lighter… faded… smaller… white characters… is a mini-sub description. It literally is near impossible to read the sub-text. A reader needs a blow-torch… and a microscope to even attempt to decipher what it says! Who the hell’s idea was that??? Whoever’s idea it was… let me make perfectly clear (yes… perfectly clear… which is the exact opposite of the clarity of the print!)… it was a terribly bad idea. (Thus the placing of this situation on Mr. Claus’s BAD-LIST!) This atrocity is then followed by a two page foreword by Jimmy Kimmel that falls flatter than his nightly monologue.
The book is “written” at the level acuity of twelve-year-old boys telling flatulent jokes and giggling to themselves in their bedroom because they think they’re hilarious and they aren’t. There is absolutely no literary artistic style to the so-called “ Writing”. My original title for my review was going to say “HUMORLESS” not “ALMOST HUMORLESS”… But to be frank… there was “ONE” funny chapter that included Sal’s agent “Baby Doll” Dixon… Lenny Dykstra… Sal… Paul McCartney… in an unscripted… non-speaking… solely observed… miniscule role… and a THIRTEEN-WORD statement by Jason Sudeikis… that is by leaps and bounds the funniest in the book!
IMPORTANT NOTE: There is no second funniest line in this ?book?

Despite the title of this book being “YOU CAN’T LOSE THEM ALL”… I can truly testify that I lost my valuable time which I can never get back… and I lost $27.05 (with tax). After reading my review… you will have at least been warned… if you want to lose the same time and money!

[Robert Poor · Rating 3 out of 5]

I first noticed Sal Iacono as a special guest, guessing the weekly NFL lines on Bill Simmon's "BS Report" podcast a dozen or so years ago. Cousin Sal, a cousin of Jimmy Kimmel and a self-described degenerate gambler, is a natural raconteur who seems to know everyone in sports and entertainment.

Here, in "You Can't Lose Them All: Cousin Sal's Funny-But-True Tales of Sports, Gambling, and Questionable Parenting," his anecdotal and conversational autobiography, he loosely ties together his life story with bemused recollections of his many woeful and often hilarious gambling losses.

This book is a quick read, an easy read, an airport read. We meet his Aunt Chippy, she of chain-smoking, video poker, and Italian cooking fame; Jimmy Kimmel as a mischievous child (not much has changed); Jon Hamm in a group photo at a Shakey's Pizza; James Dixon, the super-agent/manager who calls everyone "Babydoll;" and many others from the Kimmel-Simmons milieu.

Despite Cousin Sal's heavy gambling losses, his memoir reads as light as a feather.

[The Reader · Rating 3 out of 5]

The subtitle of the digital book is: "Tales of a Degenerate Gambler and his Ridiculous Friends." The subtitle here on Goodreads, however, is: "Cousin Sal's Funny-But-True Tales of Sports, Gambling, and Questionable Parenting." The former subtitle definitely captures the book.

And Cousin Sal definitely drops the names -- Phil Hellmuth, Lenny Dykstra, Paul McCartney, John Kasay, Mike Tyson, Tony Romo, Jim Kimmel, David Blaine, Jon Hamm, Bill Simmons, David Chang, Kenny Mayne, Neil Everett and more. Though, some are friends, some are family, some are co-workers, some are friends of friends, and then some just appear through happenstance -- i.e. Paul McCartney.

This isn't a gambling book like "Bringing Down the House" or Molly Bloom's "Molly's Game." No in depth stories of how he beat the system. Just gambling story upon gambling story upon gambling story.

[Thomas Kelley · Rating 4 out of 5]

Sal Iacono who if you watch Jimmy Kimmel you may know is Jimmy's cousin who has appeared on various shows and podcast either performing comedic skits or talking about gambling. This man in his own words is a degenerate gambler and developer of Mount Oddsmore and also happens to be a lover of girl scout cookies ( You will have to read the book to see which ones). This book has many stories related to his gambling life which started at an early age and those of his friends and coworkers who will gamble or bet on anything. I had concerns about this book one I first received it but it is quite humorous even though sophomoric at times but really what do you expect. Can you imagine holding off on filing for a divorce just to win a bet ? If you like humor and gambling give this a read.

[Ken Heard · Rating 3 out of 5]

Cousin Sal is a fun guy... to a point. I've found his skits on Jimmy Kimmel's show to run long at times and cease being funny - especially his hidden camera stuff.

The book if fun, also .. to a point. He seems to revel in his "degenerate" ways of gambling and is stunned his wife stays with him. I am too, if all what he says is true.

I've never heard his podcast, but this reads like it's a transcript of one of those. It's full of tales that, at times, are funny and at other times pretty rough. The projectile vomiting story at the eating contest was pretty gross. And if you couldn't come up with a visual in your mind of that, Sal offers a picture of it as the last page of the book.

This is an entertaining read if there's nothing else to do.

[Aaron · Rating 3 out of 5]

Cousin Sal's "Guess the Lines" episodes during the NFL season are close to the only reason I listen to Bill Simmons' podcast anymore, and this book was exactly what I'd hoped it would be.

It's not really a memoir, not exactly a gambling guide (maybe a what-not-to-do guide), just Sal telling a dozen or so of his best stories. "You Can't Lose Them All" does a good job keeping the stories entertaining. This could have just been a litany of gambling debauchery, but Sal keeps it high-level, fun, and necessarily self-deprecating--who feels bad for a gambler, honestly? (Well, maybe you do if they're a true addict...which Sal may be?)

Perfectly enjoyable and a good palate-cleanser for me personally after some heavier books recently.

[Dan Chancellor · Rating 3 out of 5]

“Every year the group gets together and settles their debts during the first game of wild card weekend at Shakey’s Pizza in Hollywood. If you’re not familiar with Shakey’s, it’s well-named. Their food is shaky at best.”

If they had called this book Shakey’s Book, it would have been well-named because the writing is shaky at best. See what I did there. The name of the book would have been Shakey, and the writing was also shaky so it would have been clever to have named the book that.

The excerpt above is about the level of writing you can expect throughout the book. I stuck with it because I like Sal, and that’s why it got an extra star here, but if you’re looking for Sal content, check out the podcasts or TV shows.

[Sumukh · Rating 3 out of 5]

You’re probably reading this book because you enjoy Cousin Sal on The Bill Simmons Podcast or Kimmel. As a result, if you’re versed in Sal, many of these are stories that come from those shows anyway.

It’s still enjoyable enough if you like gambling. But really Sal is best suited when you’re actually hearing him and in the free-flowing world of podcasts where his quick wit and hilarious reactions to whatever being discussed comes through.

This was sufficient as a book I suppose but I never laughed out loud once so clearly Sal is a better talker than writer to me if that makes sense. I guess, glad I was a cheapskate who got it from the library and read it 3 years after the fact. And glad Baby Doll got him more money for Sal’s 17th job that year.

[Johnathon · Rating 4 out of 5]

If you like Sal's bits on Jimmy Kimmel or his many podcasts, you know what you're getting here. Unfortunately, there are no bits from Parent Corner. I feel like the questionable parenting part of the title really got left out of the book. Could've made it a little longer...but the stories presented here are really funny. My favorite chapter is likely with Baby Doll Dixon--but the Lenny Dykstra / Paul McCartney one is close. Yes--the name-dropping throughout the book is constant, and it's a strength.

[Drew Tschirki · Rating 3 out of 5]

Look, it’s Cousin Sal, you know what kind of degenerate stories you’re getting.

I enjoyed listening to this while working. I don’t think his humor translates well to a book, much better “off the cuff” but it was enjoyable.

I particularly liked the Baby Doll stories. What a guy, that Baby Doll.

Also the food stories with House are relatable as I’ve had my share of battles with stupidly large amounts of food.

Ending was meh. Not sure how you really wrap up this kind of absurd memoir though.

[Aaron Ash · Rating 2 out of 5]

I had something different in mind as I went into this book which, I realize, is my own fault. The book maybe shouldn't be penalized for the this, but since the rating system here is designed to be be subjective, two stars is all it gets. This is a memoir that feels as hastily written as the author jokes about it being in its own pages. I've enjoyed listening to Cousin Sal in various places over the years. His jokes are often very funny. But this is a guy I'm sure I couldn't stand to be around and that comes through in the book in a way that makes it less enjoyable.

[Jeff Beckham · Rating 4 out of 5]

If you like Cousin Sal, this will be right up your alley

Think of this book as all the podcast stories organized and put on paper. I blew through the pages and had some great laughs along the way.

If you’re looking to learn things more useful than  to not fall asleep first at Sal’s house, then you may want to visit a different section of the library. But if you’re here to be entertained, you will be.

[Rick Jatti · Rating 4 out of 5]

having listened to the BS Podcast for years, I'd guesstimate I'd already heard 50% of the stories told in this, but I have a bad memory and only recalled portions of about a quarter of them...definitely worth a read for anyone who's a fan of Sal and his eccentric friends, not sure how much anyone else would care but it's an easy read and you can drop in for a chapter or two at a time in between other things because it's structured story-by-story

[Matthew · Rating 4 out of 5]

Fun stories about Sal's life and gambling antics with friends.

I've heard a bunch of them through his podcasts or interviews, but they're all worth hearing again. Plenty of new degenerate tidbits.

Few faves -

- How Cousin Sal and his wife met. Unbelievable and romantic.
- Story of Sal and Babydoll meeting Obama
- Anything Brad related

[Henry · Rating 1 out of 5]

As sometime who enjoys gambling, it is a bad sign that I found this very uninteresting. Perhaps you have to know the guy. It isn't necessarily bad, but I just found no reason to care about the tales. Seems like the main hook is that he is Jimmy Kimmel's cousin, but that isn't enough to make this worth the time.

[Gregg Parker · Rating 5 out of 5]

My favorite anecdote in this book is Sal's story about losing money on the first Rams/Pats Super Bowl. Over the years, I've heard him tell this story on a couple different podcasts, and each time he tells it, he lowers the amount of money he lost. First it was 20 grand, then 10 grand, and now in the book it's 5 grand. Soon he'll be saying he won $100 million and bought a rocket ship.

[Ward · Rating 5 out of 5]

I pride myself on my well-honed perspective and sense of humor - until football season, when I listen to Cousin Sal and ape his joyful, free-flowing debauchery.

Take this book to the beach, get stoned and laugh at his panopticon-style perspective, always aware of the gambler's simultaneous, dichotomic lows and highs.

[Brendan Sheehy · Rating 2 out of 5]

Moderately entertaining if you are a fan of the BS pod and enjoy some of Cousin Sal's stories there, but all-in-all not very well written and feels like most of the stories are tamed down for public consumption.

[Ian Johnston · Rating 5 out of 5]

Great personal stories

This this was a really great read. It's quick and simple. He tells great stories and has a background of gambling. The overall book is not just about gambling though they're a great life lessons and hysterical stories interwoven.

[Ross · Rating 5 out of 5]

Well worth the read

This is a fun quick read by a guy who is as genuine as he is funny. You don't have to gamble or even know anything about it to enjoy this book about Sal's life and the odd collection of people he's befriended along the way.