‘Never chase’: Pro sports bettor reflects on keys to Hall of Fame career
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The Chicago Bulls were at the start of their 1990s dynasty when professional sports bettor Jeff Whitelaw discovered Michael Jordan was going to miss a game one night.
That valuable piece of information was not readily available when Whitelaw walked into the Caesars Palace sportsbook and saw Chicago was still a sizable favorite.
But instead of betting big on the underdog, Whitelaw informed then Caesars sportsbook vice president Vinny Magliulo that the man widely regarded as the greatest basketball player of all time was out.
“I said, ‘OK Jeff, well I appreciate you telling me, go ahead and make a play.’ He looked at me and said, ‘Are you going to change the number?’ And I said, ‘Not until after you make a play,’” Magliulo said. “The reason I did that is he knew it before me and he could’ve bet it multiple times and took full advantage and he didn’t do it.
“It was classy of him to give me the information, and the old school in me, the way I grew up, is to give him the opportunity for a limit play. The fact that he gave me that information and that I could make an adjustment after his bet was going to save me a hell of a lot more money in the long run. From that point on, we became close friends.”
Whitelaw said it was simply the right thing to do.
“It’s just my ethics. I try to do things the right way. As a result, usually I have a very good rapport with most of the books,” he said. “I always tell the books whenever I have an injury. If they want to give me a bet on it, that’s fine.
“The irony is back then his courtesy bet was more than most of the books take today. He gave me $5,000 on it.”
The 58-year-old Whitelaw, who won the wager, reflected on his 35-year career and changes in the industry following his recent selection to the Sports Gambling Hall of Fame. He will be inducted in August at the Circa sportsbook.
‘Had a knack for it’
Whitelaw was born and raised in Buffalo, where he attended the same high school as former NFL star Rob Gronkowski, Williamsville North.
Whitelaw was introduced to sports betting by his father.
“My dad gambled, so I would bet a dollar and things like that on the Bills and I had a knack for it,” Whitelaw said. “I decided at a young age that was really my passion. I really enjoyed it.”
The diehard Bills fan was a disciplined bettor from the start.
“I wouldn’t bet against the Bills,” Whitelaw said. “But I would bet on them when I would like them and I would pass if I didn’t like them.”
Whitelaw graduated from SUNY Albany and briefly considered a career on Wall Street before following the sun to Las Vegas in 1990.
He worked as a ticket writer for three years at the Barbary Coast sportsbook. His goal was to eventually run a book, before he switched sides of the counter to work with a pro sports bettor.
Whitelaw has turned a profit in 33 of the last 35 years and has consulted for a bevy of books along the way, earning renown for his expertise in props and futures, especially season win totals.
“When you hang a number or you’re thinking about a price on something, you’re not going to get a better opinion than Jeff’s,” Magliulo said. “He’s definitely one of the sharpest bettors of this generation and a class act.”
‘Betting against the public’
One of the myriad ways Whitelaw has won over the years has been fading the betting public, a trend he first noticed while working at the Barbary Coast.
“Whenever I would write tickets on the same team over and over and over, they would always seem to lose,” he said. “Then when I became a bettor, I noticed I was always betting against the public.
“Still, to this day, the public typically bets favorites and (the) over and I’m more of an underdog and under bettor.”
Whitelaw said the biggest keys to his success have been discipline and money management.
“Never chase,” he said. “There are always going to be games tomorrow, so if you miss a number, just pass and be patient and wait for a good opportunity. There always seem to be good spots.
“Use good money management and bet one unit or two units or three units, whatever your unit is, and always do some due diligence. Don’t just blindly bet a game because it’s on TV.”
‘It was way easier’
Whitelaw, who is now semi-retired, said it was easier to win during his heyday in the 1990s and early 2000s due, in part, to slower information flow.
“It was way easier in the 90s and early 2000s because when you would get information on something, you might not even hear about it for a day,” he said. “Now that you have (the social media platform X) and various things, it’s a matter of seconds or a minute. You have to do things instantaneously. The days of getting information before anybody else have gone by the wayside.”
There were also many more independent books and a much greater disparity of lines back then.
“Now the lines and totals are almost identical … and the lines are sharper,” Whitelaw said. “But back in the 90s, a game might be anywhere from 3½ to 5½, so you have a middle and you have a play, and the totals would be three or four points off.
“And arbitrage on baseball. The Yankees are playing the Red Sox. Caesars has the Yankees (-140) and the Mirage has the Red Sox (+150). It’s just free money. But now you don’t see that.”
Old school
Whitelaw, a math whiz and former competitive chess player, has always done his handicapping with a pen and paper.
“I’ve worked with a lot of people over the years but I’ve never used algorithms or things like that,” he said. “You can’t compete with a computer. But it’s more of a challenge to do it myself. There’s something to be said about doing your own handicapping and not relying on a computer simulating the game a million times.”
While it’s crucial for professional gamblers to remain objective, Whitelaw remains a card-carrying member of the Bills Mafia.
“I’m still a Bills fan,” he said. “I will bet against the Bills if I think I have an edge — with the exception of the playoffs.
“In the playoffs, if the numbers called for a bet against the Bills, I would pass and just root for the Bills.”