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Teaching People To Be Better Sports Bettors with Kenny San Antonio

Written by: Bill Krackomberger
Updated October 14, 2022
13 min read

It’s episode 114 of Wise Kracks and our guest this week is a sportsbook supervisor from a popular casino in Connecticut! We also talk about the Dallas Cowboys continuing to beat the odds, a legendary boxer’s match that went under the radar, the NFL ending a long-standing tradition, and this coming weekend’s UFC Fight Night. Here we go!

Your hosts Bill Krackomberger and Jon Orlando discuss Jon’s Cowboys on the rise. Despite losing their star quarterback in the season opener, they’ve managed to win their last two games. Are things not as bad as they seem?

Boxing great Floyd Mayweather Jr. participated in a boxing match this past weekend, and if you missed it, you’re not alone! How did he fare in the Super Rizin match along with his security guard in the co-main event?

In what is a long overdue decision, the NFL has opted to end the Pro Bowl in favor of skills competitions. Do NFL fans even care?

Another MMA event is upon us with UFC Fight Night: Dern vs Yan taking place this coming Saturday, October 1st. Who are the guys picking to win?

Bill and Jon are joined by Kenny San Antonio, a sportsbook supervisor from the Foxwoods Resort Casino in Connecticut. He talks with the guys about how he got his start in the sports betting field, how he thinks customers should be treated, and his love for horse races. Hear this and more on this week’s Wise Kracks!

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Will the Dallas Cowboys Beat the Odds?

To Jon’s contentment, he continues to be surprised by the NFL season his favorite team is having. After the Dallas Cowboys lost their starting quarterback Dak Prescott to a thumb injury in their season opener, while also losing to the Tampa Bay Buccaneers, Jon’s dream of a winning season seemingly came crashing down. “I put the nails in the coffin when Dak went down,” Jon says solemnly.

However, their last two victories, including besting the New York Giants on Monday night 23-16, are changing Jon’s perspective. Jon exclaims excitedly, “That’s two in a row!” With these wins, Jon begins to believe more and more in Bill’s mantra of any given Sunday. “As I said, you just never know what will happen,” Bill mutters.

As a humble man himself, Bill makes it his duty to at least keep Jon a little humble in his excitement, “Before you get too excited, they’re only beating the Giants!”

Jon reiterates a question that he will likely bring up again if the Cowboys’ trajectory remains the same, “Do you think they’re going to win more than 10?” Bill replies with a chuckle, “I don’t think so, at least I hope not… I’ve got money riding on them to win less than 10!”

The Biggest Fight Unheard Around The World

This past Sunday, one of boxing’s greatest fighters stepped into the ring, and there’s a good chance you may have heard nothing about it. As part of a Japanese boxing league’s main event, Floyd Mayweather Jr. faced off against Mikuru Asakura where he delivered Asakura’s first KO loss. “I had no idea this was happening until it happened!” says a puzzled Jon.

“I don’t think there’s much interest in this in the States,” Bill explains, “But if they want to do it in Japan, go for it!” Jon notes that Floyd was paid $1.5M for the press conference.

Also part of the Super Rizin event was Mayweather’s security guard Jizzy Mack who participated in the co-main event. Unlike Mayweather’s fight victory, Jizzy’s ended in defeat, getting knocked out by his opponent. Jon has a couple of critiques for Jizzy, “It didn’t look like was throwing professional style punches.”

As someone who likes to stir the pot, it’s very likely that Mayweather’s security guards have their work cut out for them. With Jizzy being knocked out, Jon ponders, “Does his stock drop as a security guard?” Bill doesn’t think so, “You need street skills and common sense… in a boxing match, no, but on the street, he’d probably be able to handle himself.”

Bill Makes Friends With the Enemy

Joining Bill and Jon this week is Kenny San Antonio, a sportsbook supervisor at the Foxwoods Resort Casino in Connecticut. Kenny got to know Bill when he started making large bets at the sportsbook he supervised, and despite Bill’s endless tales of being the enemy of sportsbooks across America, they kicked it off. “I liked his attitude, simple as that,” Bill proclaims.

In the beginning, Kenny was hired as a ticket writer but quickly moved up to the supervisor role. He attributes his quick up-rank to years of betting being in his life, “Those old parlay cards, my dad would get them… I’ve been around sports betting forever.” Bill finds comfort in that story, as he himself did the same when he was, “9 or so years old.”

Beyond his attitude, Bill admires Kenny because he knows the pulse of the business,

It’s hard to get anyone that knows anything about the business… they knew you knew the industry, and that’s why they hired you right away.

Bill has always considered someone that remembers where they came from to be a great asset to the sports betting industry, and Kenny is no exception. As a purely humble guy, he makes sure his customers get the best, well-rounded experience possible,

I look at it like being a customer; I want them to be treated the way I would want to be treated.

As a supervisor, Kenny has seen his fair share of uninformed bettors, and Bill knows it all too well, “The sportsbook business is unbelievable, some people are so uneducated, which leads to uneducated bets.” Kenny agrees, “Sometimes you have to explain things to them and not lose your patience.”

Bill loves that Kenny likes to go out on the floor and talk to people because “Not many guys would do that.” At times, Kenny will try to show customers the way around a kiosk, in an effort to get them to learn, “It’s a little easier that way.”

Bill winds the interview down with a simple question, “Did you ever think you’d have the business that you have?” Kenny has to think, “I think I could’ve seen it going this way.” He thinks for a bit more,

I personally think it could be a lot better… I’d like to see more people at physical books, but it is what it is!

With their time concluding, something catches Jon’s eye, “Hey Kenny, can you go full-screen?” When Kenny’s full-screen appears, Jon points out what he saw, “He’s got horse races on in the background! That’s how I know he’s a good guy!” Kenny lets out a hearty laugh, “I love horse races!” A smile stretches across Bill’s face, “I can guarantee horse races love you back.” On that note, Kenny regals the guys with one final story,

One of my biggest hits was in horse races… I bought an apple computer with my winnings and then I blew it all. It is what it is.

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Welcome to Wise Kracks, your one-stop-shop for everything betting, pop culture, tips & more! Your hosts Jon Orlando and Bill Krackomberger dive into the sports world, all the while making each other laugh.

A new guest joins the show every week with a background in sports and entertainment with stories to share that can’t be heard anywhere else. Wise Kracks wants to help you rake in the winnings, and Bill is the man with the plan.

Tune in to the WSN YouTube channel every Thursday to catch a new episode of Wise Kracks!

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Bill Krackomberger

187 Articles

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]

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