* I Bet On The Red Sox, Won Some Money, And Had Zero Fun

Based on the sports betting ads on TV, I thought that betting would be more fun. And that this blog post would be longer.

Whenever I receive a scratch lottery ticket as a gift, I tend to sit on it for a long time (months some times). Maybe I’ll win, maybe I won’t, but I like to draw out the fun!

So when sports betting became legal in Massachusetts in August 2022, I figured that I would bet on the 2023 Red Sox season.

I often will buy (or at least consider buying) products/services that are advertised at me. I figure I’m the target market, and if I need (or want) the product/service, then what the heck!

Since I’m not a better/gambler/gamer (and I think those terms are synonyms), I had to learn some of the lingo. Like “sportsbook,” which apparently means “bookie” except nicer sounding.

I was aware that there are two major sports “gaming” apps: DraftKings and the other one (whose name I can never remember). Since DraftKings is a Boston-based company, and since I can never remember the name of the other one, I went with DraftKings. Now I’m supporting the local economy AND Red Sox advertisers – double win!

Setting up the account was harder that I thought it would be, but maybe that’s a good thing? Picking the games to bet on was easy. I’ve been sitting in (and buying a bunch of) my friend John’s Red Sox season tickets since 2008, and in those games, the Red Sox have a ridiculously good .641 winning percentage (which is 104 wins in a 162-game season).

So for the 2023 season, I bought tickets (two each) to 12 games and decided to bed $100/game on the 12 games. Did you know that you can’t bet on future games? Except for the next-scheduled game. So I had to bet one-by-one on the games. And I don’t always go. I went to 2 games this year and gave away tickets to 10 games.

For the first game, I got a slight jolt of adrenaline after placing my bet. But there was no party. David Ortiz did not show up in my living room to spray me with champagne. I did not play with friends (as suggested by the ads). In fact my friends thought that I was crazy. But I knew that this was a sure thing!

Then a funny thing happened. After 8 games, I forgot to bet on game number 9. Now what was I supposed to do? The whole experiment was based on betting on all 12 games. I couldn’t just skip one game and resume betting. Seemed wrong. So I stopped betting after 8 games and declared the experiment over.

The Red Sox went 5-3 in the first 8 games (the ones I bet on), and they went 0-4 in the last 4 games (the ones I did not bet on). If only my bookie – er sportsbook – had reminded me to bet!

Since I won money, I did not end up supporting the local economy, so that was a fail. I also did not have any fun, so that was a fail.

But I did not get addicted to gambling, so that was a win. And I donated my winnings – $146.04 – to my local church.

In summary, I won money betting on the Red Sox in 2003 and had zero fun doing so. I’ve deleted the sportsbook app from my iPhone. There’s a lesson in here somewhere.

P.S. Congrats to Major League Baseball (MLB) for producing the least-watched World Series in history! Maybe there is more wrong with MLB than just legalized betting.

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