Is the 'square' dead in today's sports betting world?

In 1967, S.E. Hinton authored the must-read book, “The Outsiders.” It featured the clash of cultures between the Greasers and the Socs.

The Socs knew it all and had it all. The Greasers were far less educated and had to scrimp and scrounge for everything they had – most notably respect.

A parallel can be drawn to the world of sports betting, particularly after it really picked up following major changes in tax regulations in 1983, which helped usher in sportsbooks to Las Vegas casinos.

You had those who really enjoyed the idea of betting, the thrill that came with having some skin in the game. But they really didn’t know what they were doing. And they earned a nickname that has long defined them: Squares.

The squares had counterparts - those who did a great deal of sports betting and were extremely knowledgeable and well connected with regard to their craft. They claimed their own moniker: Sharps.

For the better part of three decades, the sharps have owned the battle against the squares. But with the continuous rise of sports media and the 24-hour news cycle, the ever-evolving Internet age, and now Twitter and even the knowledge that comes from fantasy football, a very fair question can be asked:

Have we seen the death of the square bettor?

Four well-regarded oddsmakers/bookmakers and two longtime professional bettors take a stab at the answer.

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Scott Kaminsky, general manager for offshore betting site TheGreek.com, has seen this evolution unfold pretty much from Day 1.

“You’re talking to the right guy,” the 60-year-old Kaminsky said. “I still have a lot of square in me, but I have some sharp in me too.”

He grew up in a small Pennsylvania town, but not so small that he couldn’t get some action on games.

“When I first started in the 1970s, there was one bookie, with access to one line,” said Kaminsky, noting it was the ultimate square play, because the bettor had no advantages. “You played a parlay card, mostly college football. Where the game was pick ‘em, they used both sides at -1, so when any game was tied, they won the bet. And there was no overtime then. So if a game finished tied, you can imagine how disastrous that was for bettors.

“Everything was going against you. You couldn’t win, and you didn’t know any better. You just thought that’s the way it was.”

And baseball was equally tough to bet.

“We were betting what’s called the Eastern line, which probably no one under 50 has ever heard of,” Kaminsky said. “The juice was impossible to overcome.”

In 1983 – when the sports betting tax was lowered to 0.025 percent, after previously being as high as 10 percent – Kaminsky was working with a line service in Las Vegas when he got a nice break from one of the best-known oddsmakers.

“I was Roxy Roxborough’s first employee,” Kaminsky said. “When they lowered the tax, that made it feasible for the books to make a profit. So a couple books opened in casinos, and then all the casinos had to have them.

“That’s when the industry took off. But still, the square bettor was pretty naïve back then.”

How naïve? Kaminsky recalls one instance during a short stint at an offshore book.

“I remember a West Coast game, let’s just say it was a Dodgers game, and they were at -140. But we were offering it at -180, and the bettors were just buying it. You couldn’t get away with that now. The squares would take an underdog now.”

Particularly since the mid-1990s onward, there has been an explosion in access points to information.

“Information, over time, has educated the square bettor,” Kaminsky said, though he wouldn’t necessarily say squares have an advantage now. “I wouldn’t use the word ‘advantage.’ I would say they’ve gotten a little smarter.

“When I was betting in the 1970s, all I had was the Sporting News. Now, you have all kinds of stats. You have stats I’ve never heard of. I don’t know what the hell ‘Smash’ is. But go to PGATour.com and look it up. It’s unbelievable the amount of information out there.”

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Jay Rood came into the business a decade after Kaminsky, but still ahead of the information explosion, starting as a teller when the MGM Grand opened its book in 1993. He’s still in Vegas, having gone to the Hard Rock, back to the MGM, onto The Mirage and then Mandalay Bay. He’s been vice president of race and sports for MGM Resorts since 2007, working out of The Mirage.

Rood had an interesting first take on why squares have gotten better.

“The general public has obviously evolved quite a bit with the advancement of fantasy football,” he said. “I think fantasy is really where people have grown their appetite for sports wagering. It’s cultivating future sportsbook players for me. They have much more access to information and stats, and what really goes into the pointspread being what it is.

“Back in the day – and still somewhat today – what the public did was driven by perception. ... They couldn’t get what I like to call ‘the Cleveland Plain Dealer report’ – the information in the Monday morning injury report. As networks of bookmakers, we had consultants whose job it was to get that information. It was distributed to us, but it wasn’t available to the average player. They were kind of at a disadvantage.”

For example, Rood said, “If Aaron Rodgers didn’t practice Monday or Tuesday, that might not have been public knowledge. That just doesn’t occur anymore. By halftime of a game, you’ve got specifics on the extent of an injury – and sometimes before a player even gets back to the locker room. That is not in our column of advantages anymore.”

Rood said the squares’ advantages extend beyond fantasy, though. The Internet and Twitter have been a huge source of constantly updated information. And something else is also making a big mark now: smartphones.

“The younger generation is so tech savvy,” he said. “The average player is more savvy than they used to be. They understand how to balance parlay wagers against week in, week out straight bets, just trying to win two out of three.”

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Aaron Kessler is a generation and then some behind Kaminsky. The 32-year-old is an oddsmaker at the Golden Nugget, having worked at the downtown Las Vegas shop for eight years, since moving from Chicago. But even in that relatively limited time, he’s seen the squares sharpen up a bit.

“I’ve seen games back in the day where there are only like three tickets on one team,” Kessler said. “There’s more than that now. Every team is seeing action. The betting has sharpened up somewhat.”

And even the NFL’s TV partners, who once were loath to tie themselves to betting for fear of upsetting misguided league officials, are getting more and more comfortable with sports betting. Even in a blowout, you can catch Al Michaels on “Sunday Night Football” regularly saying things such as, “This game’s not quite over yet,” or “It’s not over in Vegas just yet.”

“ESPN’s website has a sports betting section,” said Kessler, something he lauds, even if it helps the squares who play at his shop. “With things going mainstream, it’s good for all of us. The public is definitely better nowadays than the squares were. They’re not making bad decisions up and down the board.

“You won’t just be able to hang up any old number and get that action. You’ve got to stay competitive. ... Remember the Patriots from a few years ago? You’re not gonna see 27-point spreads again. That’s very rare.”

And Kessler would like to see even more means by which squares can sharpen up.

“I’d like to see it evolve even more. People getting sharper is better for everybody,” he said. “A little pushback against the wiseguys, that’s good. More action is good for us.”

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Jimmy Vaccaro has been on the sports betting scene longer than any of the aforementioned oddsmakers – and longer than Kessler has been alive. The 69-year-old Vaccaro, currently the chief oddsmaker at the South Point, moved to Vegas in 1976, helping legendary gaming figure Michael Gaughan open the sports book at the Royal Inn Casino.

Very few people have seen more than Vaccaro. Perhaps that’s why he’s a little less likely to give too much credit to the progression of the square bettor.

“A lot of people are getting smarter, but also, more people are being introduced to sports betting, and it’s really, really hard for those people to win,” Vaccaro said. “And as far as getting smarter, you could also say the same thing about the bookmakers. We all see the same stuff. There’s not too much that’s not covered anymore.”

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Bryan Leonard is on the bettors’ side of the counter. The 53-year-old has been a professional bettor for 32 years, and he agrees that the public has made progress since the 1980s.

“Back then, square bettors just bet on whatever they saw recently,” Leonard said. “If a team looked good and they won on that team, they tended to bet on that team. They’d bet a lot on streaks. They fell into the usual traps.

“They have gotten better. You’re able to follow people who you trust, and there’s also a ton of free information now. They’re much more savvy than in the past, and if they’re not savvy, they have friends who are. Sports betting is much more in the open now.”

With more bettors, and more squares getting at least a little sharper, Leonard said the pros have a little bit less of an advantage.

“It definitely has an effect,” he said. “To have the general public out there, we’re not really playing against the bookmakers – we’re playing against the public’s opinion. And the edges for us in the past were a lot bigger than they are now.”

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Marc Lawrence, a professional handicapper and author of the esteemed Playbook publication, has been handicapping sports since 1975 and has watched the information age change the market almost overnight.

Lawrence believes that regardless of the tools available to bettors, "like a leopard, you can't change the spots on a square," and it's not so much about the information in hand but how it's used. 

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So with all that said, we’re back to the original question: Have we seen the death of the square bettor?

Have the squares become sharps, or at least something close to it? Have “The Outsiders” become insiders? Are the Greasers even with the Socs?

In a word: No.

While experts agree the squares aren’t quite so, well, square anymore, they still hang on to many of the longtime public tendencies to bet games they shouldn’t, in ways they shouldn’t, with limited bankrolls they consistently misuse.

“The squares don’t have an edge because the majority of them don’t win,” Kaminsky said. “They still make six, seven, eight-team parlays where there’s no value. A wiseguy would never do that.”

Plus, they don’t have the bankroll or the time that allows them to shop several places for the best possible number. Kaminsky said the squares may be able to stretch their limited dollars further, but the end result is the same.

“Take video poker, for example,” he said. “A full house pays better on certain machines. You’ve got better odds, and your money lasts longer. But what’s gonna be the inevitable outcome? Most, in the long run, are still gonna lose. It’s just that they can stretch it a little longer because of information.

“They’re still betting the same way they did 20 years ago. They’re not quite as blatantly arrogant when it comes to betting. They’re definitely a lot smarter. But they have a long way to go. I don’t foresee a day in my lifetime where that changes. If books cater to squares, you will never have to worry about losing to squares.”

Rood said there’s still no shortage of players who just want to score big and quickly, rather than study hard and grind, which is what it really takes to thrive in this business.

“It’s hard to sustain if you just take shots on high payouts. You need to understand how the sportsbook works. If you play straight bets and cherry-pick, you have the advantage,” said Rood, while also acknowledging that most of the squares are only out for a good time anyway. “Most players understand they’re not gonna become Warren Buffett with us.”

While Kessler tended to avoid the term “square,” he didn’t declare them dead, but rather alive and kicking – and losing.

“I was talking with some friends about this,” he said. “We all had a good laugh. The public is alive and well. They’re still taking favorites and still taking Overs. The ticket count reflects it, and the average parlay is going to have a lot more minuses (favorites) than pluses (underdogs).

“The public is definitely more informed, and the information explosion lets them make more informed decisions. But it’s hard for the average bettor to hold his nose and take the Raiders +15.5. It’s hard to pull the trigger on that.”

Lawrence believes that as long as there are people misusing the vast amounts of information available to sports bettors, there will be so-called squares.

"It’s not the arrow, it’s the archer that shoots with accuracy," Lawrence adds.

Leonard gave perhaps the best answer, by providing a better term for the public.

“I’ve heard people calling them square sharps. They know the market, they know the pitfalls, but they still do some of the things they probably shouldn’t do,” he said, specifically noting college football teasers while acknowledging one of his peers across the counter. “Jimmy Vaccaro always says, ‘Anybody who comes in and wants to bet a college football teaser, I let ‘em come in and bet whatever they want.”

That’s the squares’ biggest problem, and one they seem incapable of overcoming.

“This is my Jimmy assumption, my opinion, that the best thing the sportsbook has going for it is human nature.” said Vaccaro, citing as an example a public bettor who takes a bad loss on a Hail Mary touchdown. “He can’t stand it. He’s looking for the next thing to do. And human nature usually means a three-team parlay. The sharp guy takes the loss and heads for home. The squares are smarter than a few years ago, but they still can’t stand it when they take it in the shorts.”

Vaccaro then points to the one inarguable fact: statistics. And those don’t lie.

“Nothing has changed in the past 30 years,” he said. “Nevada’s state figures for win/loss percentage, that number hasn’t changed. In a good year, the books will win 8 to 8.5 percent, in a bad year 6 percent. We’ve never lost, and we’ve never won 10 percent. If everybody is getting smarter, that number would go lower.”

Patrick Everson is a Las Vegas-based senior writer for Covers. Follow him on Twitter: @Covers_Vegas

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