The curious case on Toronto’s Bay Street: $500,000 Super Bowl pot goes missing

Two days before the game, word started to spread: The pot had gone missing.

Every year around the Super Bowl, Bay Street stock traders and their friends participate in a high-stakes pool. Run by an old-school floor trader from the Toronto Stock Exchange, the private gambling affair is highly exclusive, and entry is open only to those with the right connections.

Given the clientele, it is no pedestrian affair. A hundred slots are up for grabs at $5,000 a piece − payable in cash. The total pot is $500,000.

For many years − possibly even decades, no one can quite remember when it began − the pool has run without a hitch. But this February, the ritual fell apart. On the Friday before the Super Bowl, according to multiple pool insiders, the organizer shared the news that the prize money had disappeared. The reason given: He’d been robbed.

The mystery of what happened to the Super Bowl cash is captivating Bay Street. A number of pool participants who spoke to The Globe and Mail were granted anonymity because of their fears that their wagers were illegal. But none are particularly upset. In fact, they were uniformly sympathetic with the organizer and his plight. Even this year’s winner, a veteran real estate financier who lost out on $300,000, said he was never angry over what played out, and gave the organizer credit for trying to fix the problem by tapping future Super Bowl contests for cash to repay those who should have taken money this year.

In the pool, winning the first or third quarters translates into a $50,000 windfall; winning at halftime means taking home $100,000; and capturing the top prize at the end of the game delivers $300,000.

In an e-mail sent to participants, the pool co-ordinator apologized for the disaster. “I appreciate everyone’s input and understanding given the unfortunate events leading to this and we will be making significant changes to the collection process going forward," he wrote. The Globe has not been able to reach the organizer.

Fundamentally, the Bay Street pool is no different than the contests staged in basements and bars across North America. It is based on a table with 100 squares; across the top are numbers from zero to nine, representing the points scored by one team and down the side is another run of numbers from zero to nine, representing points put up by their opponent.

Each square, which is randomly assigned, represents a possible score, and prizes are awarded at the end of each quarter. There’s a big prize for whoever has the correct square at the end of the game. This year, the New England Patriots beat the Los Angeles Rams by a score of 13 to 3, so the winner had the square that corresponded to Patriots 3, Rams 3 on the chart.

Two things make the Bay Street pool different. First, most Super Bowl squares see gamblers toss in $10 or $20 per entry, leading to prizes worth $1,000 to $2,000. In this version, buying one square costs $5,000 – and it must be paid in cash, preferably in $100 bills, according to participants.

To collect the cash, the co-ordinator goes from office to office with a backpack. He’s often greeted with high-fives and cheers.

The Bay Street pool also has prestige. It’s a word-of-mouth affair, and to enter you need to know someone with an inside track. These gatekeepers tend to spread the joy around by syndicating their entries, perhaps splitting a square with 10 of their friends or colleagues, so that each person pays $500.

One participant said he heard that the robbery took place in Mississauga; another said he heard that the thief trashed the house.

If the organizer was robbed, he apparently didn’t go to the authorities. Police departments in Toronto and three surrounding regions said there were no reported residential robberies on this scale in the week leading up to the Super Bowl. Constable Ryan Anderson of the Halton Regional Police Service said: “Our officers have no record of a reported theft of $500,000, and I think we would remember that call.”

The pool started out as a bet among friends and has grown over the years. No one seems sure whether the current form is fully legal.

The answer to that, according to lawyers Michael Lipton and Kevin Weber at Dickinson Wright LLP, who focus on the gambling field, likely depends on whether the organizer takes a cut. Under the Criminal Code, if he is merely holding the money for winners, and if the pool is based on a legal sport, it should not be a problem.

In his e-mail, the organizer said he “will not be taking any fees” this year or for the next four years as part of his plan to make up the lost funds. His repayment plan will take four years.

After each Super Bowl from now until 2023, there will be partial payouts for this year’s prizes, with $12,500 to the first and third-quarter winners, $25,000 to the halftime winner and $50,000 to whoever has the final score correct.

To make the math work, the size of the final prize each year will be cut to $200,000 from $300,000.

“Good luck to all,” he ends the e-mail, “and once again, thank you for your understanding throughout this difficult process!”