August 29, 2024: Bet Bet Bet Bet Bet

posted in: Bears, Blackhawks, Bulls, Cubs, White Sox | 0

Ah, the return to gambling… it’s been fun. Took a number of years off, after many rounds with local bookies and offshore accounts; sounds like I was betting a lot… not really. I think my account was shut down in Costa Rica with a few hundred bucks in there; guess I was lucky. I owed my local bookies more than that at certain points; ah, when my pockets were deep. I guess technically they’re deeper now, but life gets expensive… wife, house, kid, tuition… yada yada…. all good stuff no doubt. I had promised my wife I wouldn’t be gambling any more… and I didn’t; it wasn’t as hard as I thought. I still got to gamble in Vegas when we went, but other than that… nada on sports, unless you count elimination & confidence pools, or squares for the Bears game and Super Bowl. Then gambling started becoming legal… I started seeing these promos for Fan Duel and Draft Kings. Wait a second… I put in an initial deposit and I get $200 in free bets… this is too good to be true. It really was $200 in free bets; I started to plant some seeds with my wife. This time would be different. This time I wouldn’t be betting recklessly; I wouldn’t bet more than I/we could afford. I wouldn’t drink and bet; that was always fun… ah the 2nd half of the Bears Carolina playoff game back in the day… emptied my damn account. Betting with my heart hasn’t typically done me well either, although I can’t promise I’ll never do that again. Finally, for the NFL playoffs back at the start of 2023, my wife gave me the thumbs up; I was back, with a $100 investment.

There’s no doubt I’m a degenerate deep down. My wife always compared me to the episode of the Flintstones when Fred was betting… bet bet bet bet bet. There have been many wild trips to Vegas over the years; I think I lost enough to build a new diving board at the Flamingo I would say. It wasn’t just Vegas… I’ve been playing cards my whole life, and at a point in my life, multiple times per week; I love it. Honestly, I would bet on just about anything, like a video poker game with my childhood friend on the way to Vegas on one of our trips; he owed me a few hundred bucks by the time he landed… thankfully he did good in craps that night. But now, I’m older and wiser… not across the board that’s for sure, but when it comes to betting on sports, I have to pat myself on the back.

After 19 months, I’m up about 50 units. With the size of my bankroll, my units have been $5… sometimes more, sometimes less, but I’ve been pretty good about not chasing… not overextending on a single game that is a “lock”. Funny enough, the few times I did, I lost… of course. I haven’t had to reload; I even took my initial investment out… playing with pure profit. I’ve lived and learned… so now what? I was up more than double that at one point, but starting with the Super Bowl then March Madness this year, had a pretty rough stretch; still, we’re maintaining… and now, we sit at the start of football season… and I can’t wait. Is this something I want to become serious about? Yeah, sure… kind of tough to do the proper job with a day job that gets busy and family, and oh yeah, this blog that I’ve been doing every day for 10 years… sometimes I think, what the heck am I doing? Grinding baby, grinding…

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