A Sports Gambling Rookie Strikes Out

My name is Morgan J. Wolf and I’ve been writing about sports for 10 years. But I’ve been obsessed with sports for much longer. When I was a little kid, my dad would get the Player Register and Stats books from the NBA, long before this information was widely available on the internet. As a pint-size stathead, I would read the damn things cover-to-cover. Remember Keith Van Horn? Yeah, that awesome guy with the knee-high socks. Well, I would make it a point to remember all the fine details about him, from the big stats like how he averaged almost 20 points in first season after the lockout in 1998-99 to how he was a terrific free throw shooter (83.5% for his career). I was five years old.

So why is it that, with all my sports knowledge, I know basically nothing about sports betting? It’s been one of the biggest temptations for sports fans for decades, and it’s recently been given a path to becoming legal everywhere in the United States. I blame my lack of sports betting knowledge partially on not growing up in Las Vegas (I’m from New York), where sports betting has traditionally been legal. In fact, I’ve only bet on sports one day in my life prior to this summer.

It was back in mid-2015. I met my parents in Las Vegas for a weekend and we went to a sportsbook, among other places. I made a bet on Michael Bisping, the now-retired UFC fighter and newly inducted Hall of Famer, to win. All I remember was that I bet $100 on him to win and he dispatched his opponent via knockout, netting me an additional $200 for the victory.

That’s it. That’s the only experience I have ever had betting on sports before starting this education project. A perfect 100% record! Amazing, right? The problem is that my prior victory blinded me and gave me a false sense of confidence because I thought I had this betting thing down. Ahahaha! Oh, how wrong I was!

Here’s the thing: my wealth of sports knowledge has always been an object of pride. Simply put, I understand every facet about how all the world’s major sports work…except cricket. Haven’t managed to figure that out yet. With that in mind, betting on sports should be pretty easy, right? After all, isn’t it just about picking a winner? WRONG. That last statement is absolutely, positively, 100% wrong. It’s about analyzing the matchup and understanding the likelihood of a certain outcome.

So, let me tell you about my week of foolishness. It’s important to note that I did badly. REALLY badly. Every day, I placed six $5 bets, primarily on baseball games, though there were a few soccer matches that I bet on as well. That works out to 42 bets over a seven-day period. I also made two additional bets that I’ll talk about later. I made a snap decision on each bet, looking at the matchup, thinking about which team was better, and laying down the money. I made these snap judgments without any real regard for trends, statistical analysis, or any kind of data-driven information that could’ve helped me be more successful in my bets.

This is the first lesson I’ve learned: Particularly in baseball, just because one team is better than its opponent overall DOES NOT mean that it will win on a particular day. The 162-game MLB record for best win-loss record is held by the 2001 Seattle Mariners, who had an astounding record of 116-46 for a winning percentage of .716. Amazing, right? But they still lost 46 games. My point here is that any team is liable to lose on any given day, no matter how good it is, and a win is never guaranteed. Those 2001 Mariners actually lost in the ALCS to the Yankees, another reason why the best team statistically is not guaranteed to win.

Of course, I didn’t think about this well-known fact, and instead picked teams based on how I felt. However, I also mixed in some favoritism, another MAJOR blindspot for anyone who wants to be a serious sports bettor. In Pat Hagerty’s book Good Teams Win, Great Teams Cover, he lays out the reason why betting with emotion is likely the worst thing you could possibly do. His reasoning is pretty intuitive, but it’s worth repeating: When emotion takes over and informs your decision-making, it takes the place of logical and fact-based thinking. Emotional betting is bad and it’s largely responsible for all the gambling horror stories you’ve heard about someone gambling away their houses and life savings.

I’ve fallen prey to this pitfall myself. I’m a huge New York Yankees fan. I own three Yankees hats, including one with a houndstooth pattern (like Sherlock Holmes’s hat) exclusively for the winter, when there’s no baseball, but I still need people to understand where my loyalties lie. They played their rival, the Boston Red Sox, in a four-game series in the second half of the week. I could never bet on the Red Sox against the Yankees, and being a good Yankee fan, I have to bet money on them. Great decision, Mr. Wolf! The Yankees lost the first three games of the series in embarrassing fashion before edging out a victory in the final game. So just off of those losses, I was in the hole for $15. All because I needed to bet on my beloved Yankees instead of finding another game to put my five bucks on.

By the end of the week, I was an abysmal 15-27, for a grand total winning percentage of 35.7%. In other words, pathetic. I lost about $90 over seven days – nothing too crazy, but enough to hurt my ego and enough for a two-person meal at a pretty fancy New York City restaurant. For some perspective, professional sports bettors normally target winning percentages in the neighborhood of 56-58%, so I’ve definitely got some work to do.

Sometimes, however, unforeseen bad luck results in lost wagers. Remember the two extra bets I mentioned earlier? I placed two bets on the Real Madrid-Atletico de Madrid match at MetLife Stadium. One was a $5 bet that Eden Hazard would be the first to score and the other was a $15 bet on a Real Madrid victory. Both lost spectacularly. The $5 bet actually lost after just 44 seconds, as Atletico’s Diego Costa opened the scoring. However, the embarrassment didn’t stop there, as Atletico piled on two more goals to make it 3-0 within the opening 20 minutes before adding two more before the end of the half to make the halftime score 5-0.

Now admittedly, this was also an emotionally motivated bet (I’m a huge Real Madrid fan), and maybe betting on Eden Hazard to open the scoring was a bit foolish (Hazard isn’t known as a scorer). However, the fact that Real Madrid lost so handily is something no one saw coming. (The final score was 7-3, which looks more like a hard-fought football score). This is another lesson that I learned. Sometimes, the results of bets are so far out of the statistical norm that you have to chalk them up to bad luck.

This lesson also links to what I’ve realized that I need to do moving forward. Professional sports bettors might as well work as statisticians because of all the data they consume. The key to succeeding in sports betting in to use statistics and advanced metrics to deduce trends and discover which bets have the greatest likelihood of succeeding. After an embarrassing – and, frankly, emasculating – first week, I’ve realized that in order to grow as a sports bettor and become successful, I must immerse myself in as much statistical data as possible. Come the end of next week, I might be talking in binary code, but at least I’ll be making money instead of losing it.

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