11/02/2016 11:00AM

Bold play the key to success for Massis


Tommy Massis has been trying to beat the track his whole life. Massis, last year's winner of the Breeders’ Cup Betting Challenge, will be defending his title this Friday and Saturday in person at Santa Anita Park.

The BCBC is the world’s premier live-bankroll handicapping contest. It requires a $10,000 buy-in, $7,500 of which must be bet on the races over the two days of the Breeders’ Cup. It attracts a large field of horseplayers from all over the country. Massis, who grew up in one of Toronto’s Little Italys, off of St. Clair Avenue West, is the BCBC's most famous international participant.

On his first day at the races back in 1973, Massis saw the great Secretariat run. Not too long afterward he became a regular at the Toronto area tracks, and developed an affinity for one in particular.

“Greenwood was the greatest place on earth,” he said of the oval that once stood on Queen Street East between Greenwood and Woodbine Avenues. “It was down by lake, adjacent to one of the better neighborhoods. It wasn’t a track, it was a city unto its own. When they closed that place [in 1994] I cried like a baby.”

Massis’s attraction to Greenwood had as much to do with the people as it did the racing. He recalled one of his early betting partners. “This was a guy who refused to spend a penny on anything but horses,” Massis explained. “One day he told me, ‘Stand over there.’ ”

His partner was pointing to a very specific spot between the security guard and one of the concessions. “Then he made his big move, stealing crackers from the chili stand,” Massis reported. “Then he walked to the coffee stand and started washing them down with creamers. I smacked him in the mouth and handed him 10 dollars. ‘Go buy something to eat!’ ”

Massis wasn’t above concocting a few schemes of his own. Greenwood would run doubleheaders back then, flats in the afternoon, harness racing at night. There was a two-hour window in between, where he’d have nothing to do.

“There was a nurse on duty,” he said, “so I walked up to her at 5:30 after the last Thoroughbed race and told her I’d had too much to drink and had to be at work at 8 for the night shift. She gave me an aspirin and a glass of water, showed me to a little cot and tucked me in, telling me she’d wake me up at 7:30. I told her, ‘Make it 7:15.’ ”

A bolder scheme involved hustling his way into the track for free. That same coffee stand had a promotion where each time you made a purchase you received a stamp on a green card, either in the shape of a jockey’s hat or a horseshoe. When you got 10 stamps, the card would get you in to the track for free.

“I got one of the cards fully stamped and made a bunch of copies. Normally admission was $2, but I stood in the parking lot selling these for 75 cents. One day I got to the turnstile and handed over my card to get in. The lady looked at it and the turnstile locked. This blonde lady, the head of security, came running over to me.”

Massis went into faux informant mode, ratting out the guy in the parking lot selling them for 75 cents. Not only did Massis avoid getting in trouble, they refunded him his 75 cents.

“Growing up, the two major influences were Sergeant Bilko and Bret Maverick,” said Massis, talking about the two famous TV hustlers. “Where I grew up, in a poor immigrant neighborhood, nobody had money, and if you wanted something you had to use your brain to figure out a way to get it.”

That’s exactly what Massis has done with his horseplaying. He still has the same burning desire to beat the track, but a more mature Massis operates within the rules these days. His biggest edge comes from his unusual approach to betting. A small subset of contest players are known for being aggressive, but Massis takes aggressive to the next level. While many players will allocate a small percentage of their overall play to a couple of combinations in an attempt to crush a race, these tight combos are all that Massis plays. He does this in both cash play and tournaments. “When I’m right, I win big,” he said.

In many years, the BCBC has been won by a player going all-in in the final race. “For a lot of players, the live-bankroll contests have become about entertainment, play all day and go all-in at the end. For them, it’s a one-race contest.”

Clearly Massis doesn’t care for this strategy. “How can your strongest opinion in every contest be on the last race?” he asked.

In his cash play, Massis is a multi-race player and the absence of horizontal wagers in the BCBC has soured him a bit on the format. “I don’t like that I can’t bet how I want to bet,” said Massis. “This might be the last one for me.”

That’s hard to believe. If his past performances are to be believed, Massis is clearly a guy who wouldn’t be above a little strategic complaining to help him get what he wants. How else are you going to beat the track?