Betting in the futures market can be a slow burn.
It's difficult enough to correctly pick a winner on any given night. Now, try picking three teams, across three different sports, to win their respective championships, and going on a seven-month roller-coaster ride to see if your passion for a single city can win you a boatload of money.
Chris Brockman, a lover of Boston sports, strapped himself in for that ride when he placed a wild prop bet in October.
"Basically, a buddy and I - both die-hard Boston sports fans - were talking about futures bets before the World Series last year," Brockman told theScore on Tuesday. "So we both went in together and bet Red Sox and Patriots (to win a championship), Red Sox and Celtics, and then a prop of three or more (Boston teams to win a title) for 40-1."
With two-thirds of that prop bet complete, Brockman's attention is now directly on the Boston Bruins, who are up 1-0 in the Stanley Cup Final against the St. Louis Blues.
The first leg of the three-team wager cashed with relative ease shortly after Brockman placed it. The Red Sox were -135 favorites to beat the Los Angeles Dodgers in the World Series and won in five games.
"We assumed the Red Sox would beat the Dodgers," Brockman admitted. "But even when we made the bet, the Patriots weren't looking like a Super Bowl team."
Indeed, as we've so often seen in recent years, the Patriots - and a 41-year-old Tom Brady - faced increased skepticism. New England was 5-2 when the Red Sox celebrated their championship at Dodger Stadium, but the market soon cooled on the Patriots following three losses over a five-week span, and their Super Bowl odds fell to 10-1.
The Patriots righted the ship with two straightforward victories to close out the regular season and then proceeded to crush the Los Angeles Chargers in the divisional round.
It wasn't until the AFC Championship Game that Brockman really started to sweat, as New England was down 31-24 on the road to the Kansas City Chiefs.
"So the guy who I have the bet with, we go back and forth about nearly every Boston game," he said. "So, needless to say, there was lots of cursing and wishing we had hedged before the game since it was such a long shot. But once the game started, we knew how it was ending. We have Tom Brady and Bill Belichick. Being a spoiled Boston fan is fun."
The two friends were right, as Brady orchestrated a textbook two-minute drill to tie it up. The Patriots then won the coin toss in overtime and marched down the field to punch their ticket to the Super Bowl, which they emerged from victorious by a score of 13-3 against the Los Angeles Rams.
Now, this months-long wager comes down to the Bruins, an outcome Brockman certainly wasn't expecting in October.
"The thing is, I don't even really follow the Bruins," he said. "I'm definitely someone who only pays attention when they're in the playoffs. My buddy and I didn't think they'd be the ones to have a shot in this bet. We were banking on the Celtics getting their stuff together and make a Finals run where we could hedge big with the Warriors."
But as the Bruins mowed down their postseason opponents and other Eastern Conference contenders began to fall, Brockman realized the epic long shot may actually pay off.
"When all the top dogs in the Eastern Conference got upset early on, (Tampa Bay Lightning) especially, and (Washington Capitals), we knew the Bruins had a real shot at winning the Cup and making this insane 40-1 shot a possibility," he said.
"It's insane. Never thought it would be the Bruins who would be the ones to make this happen, but here we are."
Perhaps the most incredible part of it all is that Brockman - an on-air producer for "The Rich Eisen Show" - rarely mixes betting with fandom.
"I'm not one to normally bet on my teams," he said. "It was more of a, 'Hey, these are crazy odds, what if it happened and we didn't bet it?' So we did."
After breaking his habit for those crazy odds, Brockman is just three Bruins wins away from getting off the roller coaster and cashing in on his all-Boston bet.
Alex Kolodziej is theScore's betting writer. He's a graduate of Eastern Illinois who has been involved in the sports betting industry for 11 years. He can quote every line from "Rounders" and appreciates franchises that regularly wear alternate jerseys. Find him on Twitter @AlexKoIodziej.
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