I Parlayed Every Baseball Game Every Day For a Week and It Sucked
It may have been 2003 or so when they last allowed America’s Funnyman Neil Hamburger to be on network TV. He was on “Kimmel” and he told a joke, “Why does Britney Spears sell so many millions of albums? Because the public is horny and depressed.”
A lot has changed since then, but more has stayed the same. Maybe instead of Britney Spears selling albums it’s more about the invention of gooning and gambling apps. The symptoms have changed but it’s all the same causes. We’re still horny and depressed.
I’m not claiming to be the smartest guy around, I once bought an open bag of pretzels at the grocery store because they were half off and then shit my brains out for four days straight. But I’m not the dumbest guy around either. Notice that’s only happened once. I just feel like I need to try something that is known to be divisive before I can appropriately judge it. I smoked cigarettes for 15 years (thumbs down) I’ve watched the film “Chappie” a dozen times (thumbs up). So a couple years ago I decided I had to give gambling a try.
Out of the gate I realized gambling doesn’t actually look as cool as you think it will (Number 2 using his X-ray eye patch to cheat at blackjack, dogs playing poker, etc). It actually looks like a dude hunched over his phone, eyes glazed over only coming alive to give his screen the finger.

I pretty much got my fill of gambling, realized it was a pretty stupid addiction and mostly stopped doing it in a compulsive way. But for this piece I decided to do some real classic dumbass gambling. For a week straight I’d bet $1 on a moneyline parlay of every baseball game on that calendar day. I’ll spare you the suspense, I lost every single bet. Not even close, not even once, I lost about half the time, as is expected. Just under 100 games, roughly 14 or so a day, probably strung five wins together at best.
I don’t know what I thought was going to happen.
I mean, yeah I do. Somewhere in the back of my mind I thought if I did this and wrote down all the odds and everything I’d go back and look at my bets and a code would be unlocked like in one of those math movies. The equation would reveal itself and I’d have a system for winning. The one trick casinos don’t want me to know. Nope. I just shit the bed day after day for seven days straight. I tried different methods. All home teams, all favorites, went with my gut, went with the opposite of my gut. All losers. Unless you’re one of those pinky ring fellas scouring obscure sports books for gaps in their knowledge of Serbian women’s basketball, you’re just gonna lose a decent chunk more than you win.
The closest I got to winning was on day four when I tried a different variation in addition to my dumbass long shots: Only bet games that have favorites of -200 or more, and parlay them. I did that a few days, usually 4 or 5 legs in a bet, and I almost won one of them, but the fifth out of five games I bet on the Yankees and they lost by a run. I lost while rooting for the Yankees. I’ve never been so humiliated.
We’re all depressed and horny, but If you’re going to get humiliated by an app, you’d be better off buying a hard working naked person’s pornography videos where they call you a little weenie.
This piece is in Recommend If You Like The Baseball Issue Summer 2026. You can find physical copies in bars, cafes and stores in Chicago and Washington, D.C. The newspaper is available for purchase here.
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