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The Winning Ticket: Uncovering America’s Biggest Lottery Scam
Named a "Favorite Book of 2022" by the Washington Independent Review of Books
The Winning Ticket is an inside look at one of the most complicated yet seat-of-your-pants financial investigations and prosecutions in recent history. Rob Sand, the youngest attorney in his office, was assigned a new case by his boss, who was days away from retirement. Inside the thin accordion binder Sand received was meager evidence that had been gathered over the course of two years by Iowa authorities regarding a suspicious lottery ticket. No one expected the case to go anywhere. No dead body, no shots fired, and no money paid out. Why should they care? There was no certainty that a crime had even been committed. But a mysterious Belizean trust had attempted to claim the $16 million ticket, then decided to forgo the money and maintain anonymity when the State of Iowa demanded to know who had purchased the ticket. Who values anonymity over that much money?
Both a story of small-town America and a true-crime saga about the largest lottery-rigging scheme in American history, The Winning Ticket follows the investigation all the way down the rabbit hole to uncover how Eddie Tipton was able to cheat the system to win jackpots over $16 million and go more than a decade without being caught—until Sand inherited the case.
Just as remarkable as the crime are the real-life characters met along the an honest fireworks salesman, a hoodwinked FBI agent, a crooked Texas lawman, a shady attorney representing a Belizean trust, and, yes, Bigfoot hunters. While some of the characters are nearly unbelievable, the everyday themes of integrity and hard work resonate throughout the saga. As the case builds toward a reckoning, The Winning Ticket demonstrates how a new day has dawned in prosecuting complex technological crimes.
The Winning Ticket is an inside look at one of the most complicated yet seat-of-your-pants financial investigations and prosecutions in recent history. Rob Sand, the youngest attorney in his office, was assigned a new case by his boss, who was days away from retirement. Inside the thin accordion binder Sand received was meager evidence that had been gathered over the course of two years by Iowa authorities regarding a suspicious lottery ticket. No one expected the case to go anywhere. No dead body, no shots fired, and no money paid out. Why should they care? There was no certainty that a crime had even been committed. But a mysterious Belizean trust had attempted to claim the $16 million ticket, then decided to forgo the money and maintain anonymity when the State of Iowa demanded to know who had purchased the ticket. Who values anonymity over that much money?
Both a story of small-town America and a true-crime saga about the largest lottery-rigging scheme in American history, The Winning Ticket follows the investigation all the way down the rabbit hole to uncover how Eddie Tipton was able to cheat the system to win jackpots over $16 million and go more than a decade without being caught—until Sand inherited the case.
Just as remarkable as the crime are the real-life characters met along the an honest fireworks salesman, a hoodwinked FBI agent, a crooked Texas lawman, a shady attorney representing a Belizean trust, and, yes, Bigfoot hunters. While some of the characters are nearly unbelievable, the everyday themes of integrity and hard work resonate throughout the saga. As the case builds toward a reckoning, The Winning Ticket demonstrates how a new day has dawned in prosecuting complex technological crimes.
- GenresAudiobookNonfiction
240 pages, Hardcover
Published May 1, 2022
15 people are currently reading
188 people want to read
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Displaying 1 - 23 of 23 reviews
September 15, 2025
Rob Sand (b. 1982) is an Iowan lawyer and elected official (currently serving as Iowa's Auditor of State and actively campaigning for Iowa's 2026 gubernatorial seat). His history of being an Iowan public servant began in 2010 when he served as Iowa's assistant attorney general, specializing in prosecution for white collar crime, including the case he details in his 2022 book The Winning Ticket (written with the help of journalist Reid Forgrave).
The Winning Ticket's main story line is about a long-running and multi-state lottery fixing scheme perpetrated by a lottery employee, Eddie Raymond Tipton, the former information security director of the Multi-State Lottery Association. Using a rigged auto number generator Tipton installed on his workplace computers with his security access, Tipton and the family and friends he pulled into the scheme "won" significant sums from lotteries in various states, though Tipton eventually got too greedy and careless and got caught buying a $14.3 million prize-winning ticket himself.
Sand was the lead prosecuting attorney on the case, and his tone in this book alternates between gleefully recapping one of his career highs, to oddly sympathizing with Eddie Tipton and thinking they could have been good friends in an alternate universe, to waxing philosophically about growing up in small town Iowa (Decorah, to be exact) and telling readers how great and fair and cool he is. It's true crime mixed with a politician's almost obligatory pre-campaign life manifesto book - a combination I rarely see and definitely wasn't expecting based on the book's title and cover.
Further reading:
McMillions: The Absolutely True Story of How an Unlikely Pair of FBI Agents Brought Down the Most Supersized Fraud in Fast Food History by James Lee Hernandez and Brian Lazarte - a similar white collar crime story without the political fluff
My statistics:
Book 284 for 2025
Book 2210 cumulatively
The Winning Ticket's main story line is about a long-running and multi-state lottery fixing scheme perpetrated by a lottery employee, Eddie Raymond Tipton, the former information security director of the Multi-State Lottery Association. Using a rigged auto number generator Tipton installed on his workplace computers with his security access, Tipton and the family and friends he pulled into the scheme "won" significant sums from lotteries in various states, though Tipton eventually got too greedy and careless and got caught buying a $14.3 million prize-winning ticket himself.
Sand was the lead prosecuting attorney on the case, and his tone in this book alternates between gleefully recapping one of his career highs, to oddly sympathizing with Eddie Tipton and thinking they could have been good friends in an alternate universe, to waxing philosophically about growing up in small town Iowa (Decorah, to be exact) and telling readers how great and fair and cool he is. It's true crime mixed with a politician's almost obligatory pre-campaign life manifesto book - a combination I rarely see and definitely wasn't expecting based on the book's title and cover.
Further reading:
McMillions: The Absolutely True Story of How an Unlikely Pair of FBI Agents Brought Down the Most Supersized Fraud in Fast Food History by James Lee Hernandez and Brian Lazarte - a similar white collar crime story without the political fluff
My statistics:
Book 284 for 2025
Book 2210 cumulatively
Read
July 19, 2022It all started when a Hot Lotto ticket worth $16 million went unclaimed until the last hours of its eligibility. Then the Iowa lottery system declined to pay the individual holding the ticket, and that individual declined to fight the decision. Something was definitely fishy here. In Iowa, the purchaser of a lottery ticket and the claimant must be the same person, and the attorney general’s office knew that the claimant and the purchaser were not the same person. When they figured out who the purchaser actually was, holy cow, it turned out to be the guy in charge of lottery security for several states. This is the situation that launches The Winning Ticket.
Before Rob Sand was elected as Iowa’s state auditor in 2018, he was the assistant attorney general who cracked this fascinating, multi-state lottery scam. Sand's story has a lot crazy twists and turns, including “concealed identities, shady attorneys, innocent dupes, an ethical fireworks salesman, a crooked lawman from Texas Hill Country who hoodwinked an FBI agent, malicious computer code hidden deep in random number-generating computers, a mysterious trust based in Belize, a lying Canadian (yes, really), a missing $16-million lottery ticket, a trial national media said [Sand] would lose and, weirdest of all, Bigfoot hunters.”
Sand explains all of this with an approach similar to how he made the case’s complexities comprehensible to a jury, and he does it with as much humor as possible. Wrapped around the dramatic but wacky true-crime narrative is Sand’s pitch for the importance of rural and small-town values like hard work and doing the right thing. The Winning Ticket is a fun, quick read from a small press (Potomac Books) that I think many others will also greatly enjoy.
Before Rob Sand was elected as Iowa’s state auditor in 2018, he was the assistant attorney general who cracked this fascinating, multi-state lottery scam. Sand's story has a lot crazy twists and turns, including “concealed identities, shady attorneys, innocent dupes, an ethical fireworks salesman, a crooked lawman from Texas Hill Country who hoodwinked an FBI agent, malicious computer code hidden deep in random number-generating computers, a mysterious trust based in Belize, a lying Canadian (yes, really), a missing $16-million lottery ticket, a trial national media said [Sand] would lose and, weirdest of all, Bigfoot hunters.”
Sand explains all of this with an approach similar to how he made the case’s complexities comprehensible to a jury, and he does it with as much humor as possible. Wrapped around the dramatic but wacky true-crime narrative is Sand’s pitch for the importance of rural and small-town values like hard work and doing the right thing. The Winning Ticket is a fun, quick read from a small press (Potomac Books) that I think many others will also greatly enjoy.
April 3, 2023
I picked this book up at the Des Moines Book Festival, March 2023 after my daughter Lauren and I attended a non-fiction writing workshop that the author spoke at. It’s fascinating to read the behind-the-scenes work that isn’t clear in the news stories of a big lottery scam case in Iowa. And it’s sad to realize why Rob gave up this work to move on to the State Auditor’s position—dealing with sex offenders would be very disheartening, and depressing, and would fill me with anger. My husband served on a jury with Rob at the prosecutor’s table and Tony thought Rob was a “good guy”. This book backs up that impression, and I love his final sentences: “Do the work, keep your conscience grounded and your heart in the right place, and good things may come of it. Even if they don’t, at least you’ve done the work.” At least we have this “good guy” serving our state at the moment when I don’t agree with our leadership.
June 16, 2023
While I do not play the lottery, the idea of a story of a rigged lottery intrigued me. This also fit into a genre I enjoy reading, and that is true crime. In that aspect, the book really appealed to me.
The book is the true story of Eddie Tipton and how he rigged a multi-state lottery to produce a set of numbers and then by purchasing lottery tickets containing those numbers, he could guarantee a massive win. The story is told by Robb Sand, an attorney in the District Attorney’s office, who mostly prosecuted white collar crime.
The book had so much potential to tell a great story, but it fell short. The book contained too much information on the geography of Texas and Iowa, as well as much of the history of those two states. Enough already, just tell me the story of Eddie Tipton, how he committed the crime and how he got caught. If I want to learn about Texas and Iowan history, I will buy a book on those subjects. Two entire chapters (out of eight chapters total) were wasted on these subjects. Not that there is anything wrong with the history and geography of Texas and Iowa, but they were not relevant to the story of Eddie Tipton. These chapters were unnecessary and difficult to read.
The book also contained too much “look at me and what I did and how great I am” by the author Robb Sand. This message by the author telling the reader how magnificent he is, permeates the book. Right in the middle of telling Tipton’s story, time out for an infomercial on Sand and wonderful he is. In fact, the entire final chapter was a complete waste of paper by the author tooting his own horn about his lifetime accomplishments and feats. Of course without this chapter and the two chapters on the history and geography of Texas and Iowa, the book would have barely been 100 pages, so I suppose these chapters were included to pad the book to make it decent size for the publisher.
The chapters actually dedicated to the story of Tipton were great. Therefore, I will give the book 3 stars for that. But the other chapters were a waste of paper and the reader’s time. Otherwise this could have been a five star book if it were not for these wasted chapters.
The book is the true story of Eddie Tipton and how he rigged a multi-state lottery to produce a set of numbers and then by purchasing lottery tickets containing those numbers, he could guarantee a massive win. The story is told by Robb Sand, an attorney in the District Attorney’s office, who mostly prosecuted white collar crime.
The book had so much potential to tell a great story, but it fell short. The book contained too much information on the geography of Texas and Iowa, as well as much of the history of those two states. Enough already, just tell me the story of Eddie Tipton, how he committed the crime and how he got caught. If I want to learn about Texas and Iowan history, I will buy a book on those subjects. Two entire chapters (out of eight chapters total) were wasted on these subjects. Not that there is anything wrong with the history and geography of Texas and Iowa, but they were not relevant to the story of Eddie Tipton. These chapters were unnecessary and difficult to read.
The book also contained too much “look at me and what I did and how great I am” by the author Robb Sand. This message by the author telling the reader how magnificent he is, permeates the book. Right in the middle of telling Tipton’s story, time out for an infomercial on Sand and wonderful he is. In fact, the entire final chapter was a complete waste of paper by the author tooting his own horn about his lifetime accomplishments and feats. Of course without this chapter and the two chapters on the history and geography of Texas and Iowa, the book would have barely been 100 pages, so I suppose these chapters were included to pad the book to make it decent size for the publisher.
The chapters actually dedicated to the story of Tipton were great. Therefore, I will give the book 3 stars for that. But the other chapters were a waste of paper and the reader’s time. Otherwise this could have been a five star book if it were not for these wasted chapters.
February 25, 2023
I’m giving this a five star review with notes. I am rating it highly because I enjoyed the book as a whole and do recommend it. The book does a good job covering all the bases of lottery operations and eventually setting the scene of the white-collar ($$$) crime. The caveat on my rating is that more balanced editing could have rounded out the narrative. As a reader, I felt certain parts focusing on Sand’s personal narrative dragged on whereas more ink could have more fully fleshed out out the circumstances of the perp. I assume Rob is not planning on authoring any other books (happy to be proved wrong here) so he gets a pass for making this particular exposé mostly autobiography. I do want to sneak in a GBR as this Iowa-centric book was published at least in part by the University of Nebraska Press. Go Huskers!
December 19, 2025
This could have been a podcast. In fact, I’m pretty sure I listened to an episode about the crime. Pros: an incredible story of chutzpah and criminal justice/administrative malpractice. Cons: the sanctimony of the author. Investigators like him are the reason criminals sometimes become folk heroes. Get over yourself. There’s also a looooong love letter to rural life in the Iowa and Texas hometowns of the bad guy and the caped attorney. Unnecessary attempt at memoir that does nothing to serve the narrative.
TLDR: listen to the podcast.
TLDR: listen to the podcast.
March 27, 2023
Boy howdy does this guy love the midwest, but in a non-Jesus-y kind of way.
GREAT story but half the book is just the author droning on about how life in small town Iowa is so great. Really conflicted on this one because he also explains how circumstances can impact criminals and the opportunities they have.
GREAT story but half the book is just the author droning on about how life in small town Iowa is so great. Really conflicted on this one because he also explains how circumstances can impact criminals and the opportunities they have.
May 18, 2022
I’m friends with Rob, so I’m biased, but I really was interested in the story — wild stuff.
July 2, 2022
Please run for governor someday, Rob.
August 31, 2022
A really great read into an intense cyber crime, while highlighting the humanity and limitations of both the criminal world and justice system.
Read
March 2, 2023Interesting to read a book by an Iowa prosecutor.
June 11, 2023
Probably only good to someone in the fraud investigation business considering the focus on legal procedure. And parts seemed like one long campaign speech.
August 9, 2023
The investigation was interesting and the best part. I could've had less of Sand's personal story and background.
This entire review has been hidden because of spoilers.
October 4, 2023
Didn’t finish
November 30, 2023
A good story but a lot of campaigning as well.
July 30, 2024
Interesting autobiographical book.
December 28, 2024
Half interesting legal drama, a quarter too cheesy, and a quarter overly liberally optimistic, but in a way I appreciated
February 11, 2025
Interesting
April 6, 2025
Rob Sand should run for governor of Iowa. He's way more honest than what we have now!
July 13, 2025
Amazing story told by an amazing guy. This is the integrity and storytelling I look for in my leaders.
September 9, 2025
Audiobook 4/5
Rob Sand for governor!
Rob Sand for governor!
February 29, 2024
This was an absolutely fantastic listen! The first part, where they prosecute the guy for one fraudulent win was interesting unto itself, but the second half topped it! Appreciated the long wait, for years, before the suspicions that he must have done this more than once were confirmed. The first clue, then the investigation, the full reveal of his scam and ultimate prosecution was fascinating. Jaw dropping stuff. Felt like I was on the trail as they solved it. And yeah, they got him!
Displaying 1 - 23 of 23 reviews