Vegas wiseguy report: Sharp vs. square bettors

There's one main difference between the approach of wiseguy bettors compared to the vast majority of bettors here in Las Vegas and around the world – guys who are appropriately called squares.

Most casual bettors don’t make a profit from their sports betting hobby. This includes bettors who are relatively sharp as well as those who couldn’t pick a winner if their lives depended on it. That’s not a horrible thing either – if every bettor won, sportsbooks would be going belly up and bettors would run out of places to play. Look no further than Cantor Gaming for a prime example of what happens when the sharps beat the books over the long term.

Cantor Entertainment Technology, an affiliate of the Wall Street financial services firm Cantor Fitzgerald, made plans to issue an IPO last December, hoping to raise up to $100 million from investors for the company by offering a sale of common stock in 2013. According to the Las Vegas Review Journal, Cantor withdrew their bid last week after the detailed financial numbers showed a loss of approximately $96.6 million since it was founded in 2004.

Cantor’s books here in Vegas – The ‘M’, Palms, Cosmopolitan, Venetian, Hard Rock, Tropicana and Palazzo – have actively courted wiseguy bettors with a diverse menu of available bets, extremely high limits and the best in-game wagering technology in the world thanks to their legendary ‘Midas’ algorithm. Given the financials now available to the public, it’s clear that it’s not easy even for a Wall Street firm with deep pockets and fantastic software to earn a profit facing off against many of the best bettors in the world.

The casual sports bettor doesn’t know many wiseguy names. The biggest sharp of them all, the legendary Billy Walters, became legendary not because of his amazing success betting on sports, but because of his ability to beat the Feds in multiple criminal trials.

Another famous sharp, my good friend Steve Fezzik, didn’t earn a lick of publicity until he started winning public contests, most notably back-to-back top finishes in the famed Hilton Supercontest. The vast majority of sharp bettors and sharp syndicates are quiet and out-of-the-spotlight - guys you’re not likely to meet hanging around in local sportsbooks.

Temper expectations


So what makes a sharp bettor different from a recreational player? The single biggest difference between the two groups of players is in terms of expectations. Sharps expect to win, while most recreational players do not. But when we talk about winning percentages, the general public really has no idea of how and how much sharp bettors are actually winning.

In 1997, as I was contemplating a move to Las Vegas to bet professionally, I enjoyed a 63-percent season in the NFL. Yet on my last visit to Vegas before moving here, I was inundated with ads that showed touts who were winning at a 70-percent, 80-percent or even 90-percent clips. At the time, I didn’t have the experience to know that those numbers were completely bogus. My confidence in my own handicapping abilities were shaken by those tout claims.

Of course, after living in Vegas for a few years, I realized that nobody – not even the best bettors on earth – can win even two out of three (67 percent) of their sports wagers over the long term. Bettors can and do get hot, enjoying highly profitable streaks, but those streaks don’t last forever.

The marketing game

I personally am guilty of advertising my short term streaks as much as anybody else who sells plays to earn a portion of their living, highlighting a current short term 7-1 (87.5 percent) run here in the NBA Conference Finals. Why? Because marketing short term hot streaks sells more plays than marketing long term success does, plain and simple.

Over a multi-year period, you won’t find many bettors posting better than 60 percent winning marks in any single sport, let alone across all sports. According to Fezzik, a five-year track record of 55-percent winners in any sport is the sports betting equivalent of the Holy Grail. The ability to win just 11 out of 20 bets, long term, is enough for wiseguy bettors to grind out a substantial profit.

Grind It Out

Those percentages don't sound very sexy to casual players, especially after years of psychological conditioning from the bold headlines of tout ads. And the rise in popularity of poker over the past decade hasn’t helped the thought process one bit. In poker, we call 55:45 decisions a ‘coin flip’ - like when pocket queens face off against Ace-King all-in pre-flop.

But in sports betting, a 55-45 percentage split is called a legitimate edge. Sharp bettors are generally less interested in making big scores than they are in grinding out a profit. Winning 11 out of 20 long term allows the sharpest of the sharps to grind out a substantial profit, year after year.

Mad Math Men

Perhaps the most shocking thing about sharp bettors is that many (most) are not what we would call fundamental handicappers. Instead, they are math guys, looking for the type of positive expectation wagers that have proven to be profitable in the long term.

Sharp bettors are certainly concerned with wins and losses, but their main focus is more about betting into good numbers. Many sharps couldn’t name three players from Alabama’s national championship winning football team or Kentucky’s national championship winning basketball team, but they fully understood the value that those teams offered on the way to the title.

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