What I Learned About Gambling from Tony Soprano

Andrew Miller
4 min readJul 20, 2021

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The Sopranos brought organized crime, therapy, and lots of gambling to our TV screens — In honor of this legendary TV show (and in anticipation of the upcoming prequel), I’m listing 4 things I’ve learned about gambling from Tony Soprano & co.

Rule 1: Don’t Play High Stakes Games with Degenerate Friends

If you’re a Sopranos fan, you were probably tickled by the private high-stakes poker game with David Lee Roth, Frank Sinatra Jr., and Lawrence Taylor.

What you might not remember is Tony warning his childhood friend Dave against playing the high stakes, and Dave ignoring him to play the celebrity-filled executive poker game anyways. Spoiler alert: Dave loses — Badly.

Unfortunately, (if you’re Tony Soprano any way) you can’t just let people not pay their gambling debts, or you’re never going to be able to run a lucrative gambling operation. Nobody wants to beat up their old friend, but if you’re Tony Soprano collecting a gambling debt, you might just have to.

If the stakes are too high, and especially if an expert warns you against playing a game or tournament, avoid it.

Lesson? If the stakes are too high, don’t play. Think it’s embarrassing to not play? It’s more embarrassing to incur a debt you can’t pay (and possibly ruin your life in the process).

Rule 2: Don’t Be Afraid to Get Creative

Speaking of Tony Soprano’s old friend Dave, sometimes, you might have to get creative when it comes to turning a profit and running a profitable operation. When Tony’s childhood friend didn’t have the money to pay him back, Tony went for a win-win and found a…different way to balance the books.

The transaction isn’t shown on-screen, but when Tony has a new SUV for his daughter and new driver Meadow, we know exactly how it fell into his possession. I hate to be gauche, but handing over your SUV is probably a better long-term outcome than handing over your kneecaps.

Lesson? Tony didn’t want his friend to get involved in the first place, knowing that friendship doesn’t trump a ‘business opportunity’ — I certainly don’t recommend roughing up your friends or taking their vehicles. I do however recommend staying creative, whether it’s your hand strategy, bankroll management strategies, or even finding the right casino game to play.

Tony Soprano — don, father, and my personal gambling teacher.

Rule 3: Football Can Be Stressful to Bet On —And worse if you’re the Bookie.

Remember when Chrissy was made and had the honor of taking over responsibility for football betting and collecting wagers? I remember that for all the episodes that featured murders, beatings, and other scary situations, the stress was palpable during this episode.

I could feel the stress of dealing with a new job, being in over your head, especially in a role you thought you’d excel in. Every time I found him lolly-gagging I yelled at the screen, and I was cringing when he didn’t have the correct sum of money to give Pauly. Lesson learned: It’s stressful to bet and lose money on a football game, but it’s even worse to run the books during a football game. Or worse, the Super Bowl.

Lesson? Maybe this isn’t a lesson from Tony himself per se, but it’s a nice reminder when your ultra-stacked parlay doesn’t hit, that things could be a lot worse.

Rule 4: Manage your Bankroll (Avoid a Vig)

If you can, avoid taking out a vig.

Remember when Tony (seemingly out of nowhere, we might add) developed a gambling problem? The audience saw him gamble throughout his life, splashing out cash, and even cautioning his friends and family to avoid the activity, yet it never seemed like he had a problem managing his bankroll.

Until season 6, episode 16 when Tony borrows $200,000 from long-time family friend Hesh to bet on a ‘sure thing’. When he doesn’t earn a profit, Soprano offers to pay him the vig — interest on the loan — versus repaying the loan in full, which Hesh wants.

We see the beginning of a deteriorating friendship due to gambling and unpaid debts, and although Tony repays the debt by the end of the episode, it’s clear there’s a fracture in their friendship.

Lesson? There’s no such thing as a sure bet. Don’t take out loans you can’t repay, and avoid borrowing substantial amounts of money from friends.

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Andrew Miller

Content Writer • Gambling buff • Food lover • Explorer • Lifelong Bacon Junkie • Beer Nerd • Thinker https://www.gambleonline.co/