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Posted by on Jan 23, 2014 in Blog, Personal, Sports Betting | 5 comments

How I Lost $39,000 on the Super Bowl


nolan-dalla (2)


If you don’t like bad beat stories, then skip today’s article.

Six years ago, I suffered the worst gambling loss of my life on a single event.

Super Bowl XLII cost me $39,000, by far my most costly loss ever.  To put this into perspective, that money was pretty much everything I had — my entire gambling bankroll.

Here in Las Vegas, it’s been said all gamblers go broke at least once during their lifetime, and this was my turn to do penance.

Here’s the story.


Before the big game, the most I’d ever bet on any sporting event was $5,000.  I’d made many bets of that size, but nothing greater.  So, what would possibly compel me to wager almost EIGHT TIMES that amount on a single contest, which also happened to be one of the worst games to bet of entire football season?

SIDE NOTE:  The Super Bowl is typically one of the worst games you can bet on, because there’s no value to either side or the total.  It’s the most hyped game of the year, and there simply isn’t any value to betting on the outcome, with the exception of propositions.  Despite this, many serious gamblers — and most recreational bettors — make this a significantly larger-than-average wager, when it actually deserves either a pass, or a much smaller-size bet. 

Everyone remembers that year.  The New England Patriots seemed destined to win the championship.  In 2008, they became the first NFL team to post a perfect record in the regular season in 36 years (since the 1972 Miami Dolphins).

The Patriots weren’t just winning their games.  They were destroying whoever they played.  About halfway through the season, local and offshore sportsbooks began taking wagers on which conference would produce the Super Bowl winner.  In other words, you could bet either the AFC or the NFC.  It should be noted the Patriots are an AFC team.

For some reason, many sportsbooks were slow to react to the dominance the Patriots were showing.  By the time New England was 10-0 and coasting to an easy divisional title, the AFC was still favored by just 3 points in the future matchup.

I won’t get too technical here.  But even had the Patriots not represented the AFC, that conference was clearly superior and would still likely to be favored in the Super Bowl, given the balance of teams.  The AFC wager was an absolute steal at that number, almost certain to increase by a significant margin if the Patriots continued their roll.

I unloaded $3,000 at a time.  The AFC to win at -3.  The AFC moneyline, at -150.  $3,000 here, and $3,000 there.  A few days later, the line increased to AFC -3.5 and the moneyline moved to -165.  I continued to bet in $3,000 increments.  Other serious bettors were doing the same thing and by the time the frenzy ended, I was holding $39,000 in action on an AFC team to win the Super Bowl.

Now, here’s where an explanation is needed.  Non-gamblers may not understand this.  The objective of wagering is to get the best of it, in other words to somehow swing the odds in your favor.  This wager had nothing to do with my feelings of the Patriots, being in action, or satisfying some emotional craving.  It was all about investing in a favorable betting situation.

Perhaps the best analogy I can give non-gamblers is to ask how much money you’d wager on a standard coin flip, with the caveat that if it loses, it costs you even money.  But if it wins, then you will receive back 2 to 1.  That would be an astronomical advantage, and you’d have no trouble going around town and raising whatever cash needed to bet the maximum.  A wager with 50 percent positive theoretical value would be a far greater mathematical return than anything a stock investment could bring.  Of course, the downside is being wiped out and losing everything.  Gambling isn’t necessarily picking winners.  It’s about putting yourself in a favorable situation.

The Patriots’ success continued.  By Christmas, New England was a perfect 16-0 for the season.  The playoffs began and they went on to wipe out both of their opponents and were destined as the AFC representative in the Super Bowl.

So far, everything had gone perfectly according to plan.


When the Super Bowl line came out, I felt as though I’d pulled off a coup.  Not just for a small score.  But big money.  New England opened up at -12 versus the New York Giants.  Here I was holding $39,000 worth of tickets at New England -3, and -3.5, and some moneyline action at about a third of the current lay price.

This became the perfect scalping opportunity, or chance to “middle.”  In other words, keep all the New England action at the low number, and then bet the other side, taking the New York Giants at plus 12 points.  That would have given me an unheard of point spread middle — amounting to 8.5 to 9 points, an astronomical figure in any sporting contest, let alone a Super Bowl game.  I mean, this was just unheard of.  I doubt anyone in history had ever picked up a 9-point middle on a Super Bowl game.

This meant that if the game hit the “middle,” which means New England won the game by between 4 and 11 points, I stood to make close to double the $39,000 figure.  This amounted to a potential $78,000 middle.


Gambling is about greed.  The very best gamblers insist they’re not greedy, that the methodology is largely about line shopping and getting into favorable spots.  But fact is, we all want to win, and not only that when we do win, we want to win even more.  It’s just the nature of what gambling is.  What’s the point of gaining and edge and then betting it for the minimum?

The scenario I described about middling a game for $78,000 (this is a rough estimate, I don’t recall the actual numbers) would be a dream for any investor.  Just get a hold of another $39,000 somewhere and pound the other side.  Then, I could watch the game with essentially little or no risk.  Freerolling for nearly 80 grand.  What a sweet spot to be in.

Then again, why would I bet against a juggernaut team like New England, which had stampeded into the Super Bowl and seemed destined to at least cover -3 or -3.5.  Why would I wager on a surprise team like the NY Giants, who were lucky to even be in the championship game?

This game had “blowout” written all over it.

Famous last words.


The temptation was to bet the Giants and go for the middle.  But I didn’t have $39,000 laying around and besides, why would I bet so much money on a team that I wasn’t sure could cover?  Wouldn’t that defeat the whole purpose of scouting out the great early number?  What was I going to do — give that advantage back by now playing the Giants just because I wanted to avert any risk?

Of course, I could (and should) have partially hedged the wager, which makes perfect sense as the compromise strategy.  Keep all the action I already had, and then bet $20,000 or whatever on the Giants going for the middle.  That way, I could either lose around $19,000 (small chance it seemed), win around $17,000 so long as New England won the game and/or covered -3.5, or win around $55,000 if I middled the game.

Anyone else getting sick of all these numbers?  Well, so am I.  So, let’s get on with the story.


I don’t watch pre-game shows or follow the hype.  I rarely watch SportsCenter anymore.  I’m just tired of all the talking heads.

On the way to the Bellagio, which is where I planned to watch the game in a private suite with several friends, I received a frantic phone call.

“Brady’s limping in the pregame warm-ups,” the voice said.

“Limping?  How in the hell is that happening?”

“They’re saying Brady might not be at 100 percent today.”

Talk about an eye rolling moment.  The game was about to start in 20 minutes, and now I was hearing bad stuff about my team.

But I had come way too far by this point.  There wasn’t much I could do.  I had about $5,000 in cash on me, pretty much everything at my disposal for betting.  It seemed pointless to run to the betting window and bet whatever I had left on the Giants, just because I got a last-second phone call that Tom Brady’s ankle decided to flare up at the worst possible time.

Action was on, and I was committed.  Patriots all the way.


The Patriots played a sloppy first half.  But the Giants offense looked even worse.  At halftime, the score was New England 7 and New York 3.  The Patriots were winning by 4 points, which suited me just fine.

It was hard to imagine the Patriots playing worse in the second half.  Obviously, they performed poorly in the first 30 minutes.  But surely they would turn things around and blow the Giants out in the second half.

The halftime line came out at New England -7.  Incredibly, even with an entire half of football already played, I still had the chance to go for a huge middle, about the same situation as pre-game.  I could have bet the Giants at +7 and still had about an 8-point middle.  Moreover, I could have certainly borrowed whatever I needed from my friends in the Bellagio suite, some of whom were serious gamblers and had big betting bankrolls.

I decided to take my last $5,000 and hedge.  That way, at least there was no way I’d end this day broke.  What I didn’t figure were the crowds at the Bellagio that day and the long lines inside the sportsbook.  By the time I made it downstairs with $5,000 in my hand ready to shove on the Giants, the second half had already kicked off.

Now, I was really committed.


The time frame between 5:30 and 7:30 pm on February 8, 2008 might have been the most torturous two hours of my life.

Not only did New England fail to do much with the ball, the Giants actually gained the lead late in the game.  I was also going to lose all my moneyline bets!  I started hyperventilating.

Making things considerably more uncomfortable were the intense surroundings.  Several other gamblers were packed inside the Bellagio suite watching the game, and many were on the Giants.

One gambler in particular was named Little Larry.  He was a real worm.  He was like 5’2″ and wore shorts and a plain white t-shirt and this was in early February.  Probably from New York or somewhere back east.  Imagine a guy like that.  Little Larry had made a bunch of small wagers — all tied to the Giants and the Under, and he was giggling like a schoolgirl.  It was driving me crazy.

The television announcer would say, “….and Brady’s back to pass, here comes the Giants pass rush, Brady goes down for another sack!” 

Meanwhile, this guy named Little Larry was jumping up and down on the bed and laughing hysterically.

“Brady’s sacked again!”

“He, he, he, he, he, he, ha, ha, ha, ha, ha, ha………………”

“The Patriots continue to trail and are now forced to punt!”

“He, he, he, he, he, he, ha, ha, ha, ha, ha, ha………………”

“This is looking to be the greatest Super Bowl upset since Joe Namath’s Jets in 1969!”

“He, he, he, he, he, he, ha, ha, ha, ha, ha, ha, WHA, WHA, WHA, WHA, HO, HO, HO, HO………………”

This was a borderline nervous breakdown.

The torture only got worse as the minutes and final seconds ticked away.

All serious sports bettors have egos, and Little Larry was certainly no exception.  After he laughed and rolled off the bed each time, during the commercials, he’s then lecture everyone in the room on why he was so smart and how he had the right side of every bet.  Not only was the indignity of losing a whopping $39,000 hanging in the air, we all had to sit there and listen to Little Larry’s sermon.

A fucking madhouse.  I don’t know how I got through it.

The Patriots did make a game of it at the end and actually took the lead with a couple of minutes left.  Then, the Giants pulled off one of the greatest plays in Super Bowl history on a 4th down where the receiver made a circus catch.  That was the final nail.

Little Larry giggled some more, lectured us all again, and by then I had totally run out of expletives.


The walk through the hotel, out to the car, and the drive home was a complete fog.  I don’t remember any of it.  Like being punch drunk.

I do remember being in a rage, that this was perhaps the biggest chance I’d ever have to getting close to a six-figure bankroll, and then potentially really become a player.  Now instead, I’d have to grind it back up at $200 to $300 a game and somehow try to rebuild what had been lost.  The other option was to quit betting altogether, which I’ve considered doing more than a few times.

But we can’t change fundamentally who were are.

Once again, I’ll be wagering on this year’s Super Bowl.  So, if someone out there has Little Larry’s phone number, please ask him to give me a call.

I could sure use a winner.




  1. “The Super Bowl is typically one of the worst games you can bet on, because there’s no value to either side or the total.”

    I strongly disagree with this statement because there is so much more money bet on this game than any regular season or playoff game, this is one game where the “public” money can swamp the “sharp” money. You almost always see the line out of synch with the moneyline, for example, year after year. Even discounting props and considering only the line and total, this is arguably the single most profitable athletic contest to bet all year.

    “One gambler in particular named Little Larry had made a bunch of small wagers — all tied to the Giants and the Under, and he was giggling like a schoolgirl.”

    As I recall, while LIttle Larry did indeed make a bunch of tiny bets he was excited about, he spent most of his time waiting for something to happen, and the exclaiming something like, “Oh, we couldda had New England to punt before they score in the second half at -170,” or something, “We shouldda bet that!” over and over and over and over again.

    If you had done him grievous bodily damage that evening, I wouldn’t have seen a thing.

    • I remember that game 🙂

  2. Nolan, great story. I also bet on sports sometimes but I realize I am just an action junkie when it comes to betting on European soccer and the world cup. In 2010 I wagered $5k on the Netherlands to win the entire cup at 12-1 before any games were played. When the beat Brazil I was looking good.

    In the final they faced Spain and on the no-tie line they were only +165 dogs. I had a $60k payday.

    Now I think betting many times as a hedge or middle just exposes you to move VIG. I have wagered lost of money on poker and BB but payouts never like this. I got nervous and decided to hedge my bet enough where I would either win $5k if Spain won or about $52k if my team won.

    I lost the big bet when spain won with 2m before penalty kicks.

    I was never close to betting my entire BR so I really appreciate your gamble here. LOL

  3. “The other option was to quit betting altogether, which I’ve considered doing more than a few times.

    But we can’t change fundamentally who were are.”

    Not true. I stopped betting sports after the 1998 Super Bowl. It was Super Bowl Sunday and I still hadn’t bet the game. I was sitting on my couch looking down at my coffee table. On the table was a wooden rocking horse my Uncle Denny had made in his woodshop and given to me as a Christmas present. I looked at that thing and thought, “Horse. Bronco. Horse. Bronco.” The Eureka moment had happened. I hustled down to the nearby Sports Book which was across the street from where we lived at the time. When I got up to the teller after checking out all the proposition bets and such I told the guy to give me…Green Bay. I’ll take Favre over 2.5 passing TD’s and on and on, making 6 bets altogether. Ended up losing all 6 bets. This is crazy, I thought afterwards. This is nuts. I’m not betting another sports game ever again. And I quit. Haven’t bet since and that’s been what 17 years? My leak was betting sports. I had no shot at being in the black at the end of each year. So I fixed it. It’s amazing how my bankroll has grown since then. I might someday go back to betting the NFL if I can ever figure out what side the fix is on. But only then, only then.

  4. Re: Gambling & Money Psychology

    A lot of pro gamblers that always hover close to being broke seem to unconsciously enjoy the “game” of being broke itself with all the challenges & stresses of rebuilding a bankroll on top of the actual bets themselves.

    I’m not necessarily pointing towards Nolan and I know it sounds crazy when I say some gamblers may enjoy being close to broke, but it seems to add an unconscious new dimension of “game playing” while engaged in the struggle to rebuild funds.

    A bet made close to the broke redline can have a lot more visceral excitement than having a $250K bankroll and making a boring old ho-hum $1,100 bet trying to follow half-Kelly criteria, for instance…

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