Blackjack Tips, High Rollers and Losing Half a Billion Dollars (Wise Kracks Ep. 53)


The latest episode of Wise Kracks is here, with your hosts Bill Krackomberger and Jon Orlando.

Bill is on semi-vacation this week, which basically means he’s checking out casinos in a different part of the country.

He’s calling in live from Boston, while Jon is back in the studio in Vegas. He also spent the previous week playing video poker in California, and Bill gives us an update on how his sessions have been going.

After a losing session the last time he was on the East Coast, Bill was overdue for a big win – and Krack doesn’t tend to wait too long.

It’s a packed show this week, and the guys start off with rounding up the latest sports news.

This episode was recorded before game six of the NBA Finals, so Jon doesn’t yet know that the Bucks have defeated the Suns – and finally put to bed his big prediction that Phoenix were going to win.

Bill is full of interesting casino stories this week.

He tells us how he was recently banned from sitting at the blackjack table with a high roller buddy of his, and why the casino is wasting its time with rules like that.

If they think the guy is going to listen to Bill to try to get an edge, they clearly don’t understand the ego of super high rollers.

That gets the guys talking about blackjack strategy and card counting.

Jon throws out different spots to Bill, and he explains how the basic strategic decisions change depending on the count, even when it feels counterintuitive.

Even though Bill is extremely skeptical about variations like Free Bet Blackjack, he does have one great tip to make the most out of one of the side bets available. They also talk about getting thrown out of casinos for being too sharp.

Special Guest Al Deleon

We’ve got a special guest on the show today, and he’s the perfect guy to pick up the theme of insider casino stories. Al Deleon has worked as a high-end casino executive in some of the top venues in Vegas, and he’s here with all kinds of juicy stories.

Al talks us through his rise through the world of casinos and gambling, from coming up on the riverboat casinos in New Orleans to making the move to Vegas, and all the connections he’s made along the way.

Al is full of stories.

There’s the guy who checked into a room on the Vegas strip and ended up staying for 2 years – and walking away with a half a billion-dollar gambling debt. He knows all about the perks of the job, like sitting courtside at the Chicago Bulls with a client.

He even gets into what you do with a high roller who is getting fully comped by a casino, but won’t gamble.

This week’s episode is stuffed with insider nuggets about high-end casino gambling, and the guys even find time to jump into some listener questions at the end.

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Bill Krackomberger

Expert on Top Picks

Billy “Krackman” Krackomberger has made his living as a professional sports gambler for nearly three decades. You have seen him on ESPN, Gaming Today, and SiriusXM. His connections in the sports gambling industry run all the way to the top. His bets move the lines and regularly have him banned from books for being too sharp.



Email: [email protected]