‘Captain Jack’: You never master sports betting; you just continually get a little better

LAS VEGAS — At that first BetBash in Jersey City, New Jersey, in 2021, Jack Andrews sensed that all the sweat and toil that Gadoon “Spanky” Kyrollos had put into this unique sports-betting conference would make it gargantuan.

It wasn’t about attracting sponsors to fund the event, saturating it with their brand.

“Spanky realized that bettors don’t want to be told what to do,” Andrews said on the first day of BetBash V on Aug. 12. “They want to learn from each other. In Jersey City, it was a four-hour open bar.

“At the end of the four hours, Spanky got on the microphone and said, ‘We’re having so much fun, the bar is open for another hour courtesy of [friend] Mike.’ I later asked Spanky how much that cost Mike.”

Spanky the Showman grinned and said, ‘‘Nothing.’’ The open bar always had been slated for five hours, but he had four scrawled on announcements to create a dramatic extension speech.

“The fact that Spanky gets it like that,” Andrews said, “he sees three steps ahead and understands that people will go crazy for that, and they’ll remember his generosity. He knew he’d have a success with this.”

The world was emerging from the coronavirus confusion, so Andrews — known to all in the gambling business as Captain Jack, with nearly 40,000 followers on one social-media outlet — was eager to see and chat with other humans.

Plus, he and five others were launching the sports-gambling site Unabated.

“There are few people out there who will tell you the truth about sports betting,” Captain Jack said. “A lot of people will sell you something, sell you picks, sell you their service. Very few tell you how to actually do the art of sports betting.

“Or the aftereffects. Like, if you win, you’re going to get limited. Where can you play and not get limited? Unabated has always been a tool, we hope, that is one step ahead of the rest of the industry.”

Sportsbook fame

Captain Jack has attended every BetBash, the last four in Vegas.

At a Circa bar on a ledge overlooking its mammoth sportsbook, Andrews, 50, was about to drop into a huge crowd of BetBashers that Tuesday evening when I corralled him.

“I’m sportsbook-famous,” he said. “I can’t walk anywhere else and people know who I am. But I can walk into a sportsbook, and they go, ‘Hey, Captain Jack!’ I like it that way.”

In 1999, the Jersey native pulled off his first Vegas adventure for a bachelor party. Bellagio had just opened, and they crammed four to a room. He calls Steve Wynn’s creation “amazing, fantastic and grandiose.”

Andrews had only known Atlantic City.

“A bunch of people with buckets of coins and dirty fingers, all getting on a bus to go home. A dump. I see Vegas and . . . wow! I want to figure out how I can spend more time in this!”

He returned east and researched gambling, which led him to counting cards at blackjack, to other table games for bigger edges, to online casinos, exploiting promotions and, ultimately, sports betting.

“I was playing with every bookie in New Jersey, and every offshore I could get ahold of,” Andrews said. “I was coming to Vegas often. I was trying to be a formidable sports bettor, which is where we wind up today.”

A certain dynamic

Compared to droves eager to register for BetBash V and hit that ledge bar for free drinks, Andrews appeared late that Tuesday to obtain credentials for panels, seminars and other events.

Captain Jack had been dining with royalty, Michael “Roxy” Roxborough, the Vegas legend and 2023 Sports Gambling Hall of Fame inductee who has participated in every angle of sports betting.

“We’ve been good friends for years,” Andrews said. “Roxy always has a million stories. A great guy, the best. We share a lot of information.”

He might be following in Roxy’s footsteps, in yearning to learn and, to a degree, sharing those finds. BetBash V attracted nearly 700 attendees, a record.

“There’s a certain dynamic when it comes to sharing information,” Captain Jack said. “The larger the circle you share information with, the less information you should share, the more risk that you’re giving away too much.

“With a smaller circle of sharing information, there’s less risk, and the greater you can share things. I tell people, network and create small groups, then share and grow with each other.”

I had just greeted Peoria residents Ryan Jeffery and Peter Ray, co-founders of Good JuJu betting, who were reinvigorated at last year’s bash. They’re now on YouTube and remain bullish.

“Sports betting is a lot like poker, like chess, like golf: You never master it; you only just continually get a little bit better,” Captain Jack said. “I am a better sports bettor than I was 20 years ago. Am I the best in the world? Absolutely not.

“You always have to realize that somebody else is doing it better, and you always have to try to aspire to something more than what you are.”

Timely wagers

Like the previous two editions, this black-tie, four-course dinner affair in Circa’s Galaxy Ballroom was grand, befitting the inductions of new SGHOF members.

Spiros Athanas, Jeff Whitelaw and Paris Smith, former chief of offshore titan Pinnacle, were honored, as were, posthumously, George Chonoplis, Leo Hirschfield and Eugene Nolan.

Whitelaw had much to say, highlighting meeting Pete Rose at Mandalay Bay. Whitelaw provided him with six baseball plays. Only five won, so Rose’s six-team parlay fizzled. And he moaned.

You, Whitelaw said, only got a hit three out of 10 times! Rose strolled away and lifted his left fist with a thumbs-up.

The dramatic evening overcame Smith several times. She did generate rousing applause when she said she had more stories, but Whitelaw had usurped all extra time.

At my table, in a ballroom corner, every other guest would have appreciated the action. The kid from Chicago tapped his cell-phone timer, triggering a four-minute total on every speaker.

All nine of his pals partook in the action; robust exchanges of 5s and 20s followed every speech. One flew past four minutes, generating a new 6:30 total. It eked to 6:27, 6:28, eliciting groans and small cheers.

When the speaker stopped at 6:38, more 20s flew across the table.

A capital T

I asked Captain Jack why operators in Illinois, being gouged by Gov. JB Pritzker in escalating fees and taxes that Andrews called “egregious,” don’t pull out of the state.

“They should,” Captain Jack said, “but I don’t think they will. Operators made this bed for themselves when they ‘agreed’ on a 51% tax rate in New York, so Illinois has every right to just go all the way up to 51%.

“Illinois is a huge market for [operators]. They’ll just swallow it, and, unfortunately, it flows downhill to the consumer.”

He says politicos desperate to plug budget gaps won’t do so via sports betting.

“You know the industry to plug it, though? Internet casinos, which they’ll eventually legalize. Trust me, internet casinos are dangerous. Trouble. Bankruptcy in your pocket.”

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