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Sunday Shootaround: What did you expect would happen?

We’re all shocked to find gambling going on here

Paul Flannery's avatar
Paul Flannery
Oct 26, 2025
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Way back in the previous century when young men had to go through increasingly shady means to get their gambling fix, I saw numerous friends get dragged through the ringer. Many of them owed money, lots of money, to the wrong people. These people were connected, as we used to say, and it wasn’t a question of if my friends would pay their debts. It was only a question of how they would get the money.

Bail me out, they said. Just this once. Implied in their pleading was the supposition that things were about to turn their way. Just a bit of bad luck. Then the games would start and they would learn – yet again – an essential lesson about gambling: Luck’s got nothing to do with it.

The people who make the lines are smarter than you. They are not in this business to lose money. You are. This newsletter doesn’t take a dime from gambling companies and it never will because it doesn’t intend to profit from other people’s misery.

From the time I started watching sports in the early 80s until the early 2020s, we were told that gambling was the red line that sports couldn’t cross. You could be an abusive drunk with a cocaine problem, so long as you didn’t play the horses in your free time. The reason was simple. The public has to believe the games are on the level. Otherwise, it’s not sports. It’s a work.

That all changed when leagues decided they couldn’t say no to all the free money the newly legalized gambling concerns were offering. I have no sympathy for the NBA now that it’s being dragged through the gutter of FBI investigations and unsavory associations with the wrong people. Not when it’s impossible to even watch a game without being inundated by propaganda about prop bets and parlays.

I do have empathy for the young men – and it’s mostly young men – who are growing up in a world where they have a casino in their pocket. Goaded into making emotional bets by a 24/7 advertising blitz co-starring Shaquille O’Neal, David Ortiz, and all the other heroes of their past, this is shameless stuff all the way around.

It’s a bummer, as many of my former media colleagues have pointed out, because this latest scandal has overshadowed an otherwise strong start to the NBA season. Like my friends learned back in the 90s, it’s too late now. You’ve already taken the money.

In this week’s Shootaround, numbers that explain the Celtics shaky start and a look ahead to next week when their season has the potential to go off the rails before it even leaves North Station.

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