To hedge or not? The big dilemma facing Blues bettor

Blues' fan doesn't plan to hedge 250-1 bet on Stanley Cup (2:51)

Scott Berry has a $400 bet at 250-1 odds on the Blues to win the Stanley Cup and has no plans to hedge the bet. (2:51)

How does logic prevail when you're a true fan? How do you remove emotion with major money on the line, especially when your passion and fandom enabled this glorious position?

That's the dilemma facing Scott Berry, who can cash $100,000 if his beloved St. Louis Blues win the Stanley Cup. It stems from a $400 futures bet (250-1 odds) placed in January when the Blues held one of the NHL's worst records.

The central Missouri native said on "Daily Wager" he has not hedged his position, which would have entailed a bet on the Boston Bruins once the Blues reached the Stanley Cup Final. That would have locked in a guaranteed profit around $40,000. Additionally, through PropSwap, a third-party marketplace not associated with any casinos that allows bettors to buy and sell bets (an eBay for bettors), Berry has received several offers to sell his ticket throughout this postseason. Currently, could get $75,000 (minus 10 pct fee) to not worry about Games 6 and 7. The Bruins are now listed at +250 to win the series at Caesars Sportsbook, meaning Berry can make $25K for every $10K wagered on the other side.

Hedging is a fascinating topic in the gambling world. Emotion is the common thread. In blackjack, insurance is never mathematically justified (unless you are counting cards). Yet, recreational players occasionally take even money on their own blackjack hand when a dealer shows an ace, forgoing the 3-to-2 payout to avoid a push. The allure of avoiding disappointment and securing profit wins out -- and similar opportunities routinely present themselves to sports bettors.

This goes well beyond the simple form of wagering on the Bruins to win Lord Stanley and waiting out the series. With the growing popularity of in-game wagering, bettors can manage their positions like a stock portfolio. Individual game bets and alternate spreads enter the equation. This approach can actually amplify winnings beyond the $100,000, although the tradeoff of getting too cute can induce even more stress, sub-optimal bets and even a net-negative ultimate outcome. It's a dangerous game to play, especially for a novice bettor unfamiliar with the betting market's ebbs and flows.

Every bettor has their own protocol. I have encountered similar situations over the years. Personally, one caveat is treating any hedge as a separate entity. Handicap the game. Do you like the Bruins in Game 6, if you did not have that futures ticket in your back pocket? Also, Berry could travel to a state with legalized gambling and bet during the game, piloting his bankroll as the game unfolds. Or wait and do all that for Game 7.

But for me, there are limitations to that general mindset. Once you pass a certain monetary demarcation, robotic behavior vanishes -- and $100,000 is still $100,000. Operating in a vacuum is impossible so I certainly approach the betting angles differently, if certain dollar figures present themselves. Everyone has their own appetite.

Berry has wanted no part of this. He told me on "Daily Wager" that any bet against the Blues would feel like cheating or inappropriate. I encountered the exact same attitude and stance last year when the Vegas Golden Knights reached the Stanley Cup Final. I flew to Las Vegas for a story and met fans sitting with odds as high as 500-1. They weren't budging, and Berry is cut from the same cloth. Additionally, Berry is the St. Louis superfan right now, finding himself interviewed by local media and national outlets like NBC's pregame broadcast.

To the uninitiated, it comes across as greedy or stupid. Both are deadly sins when it comes to money. But it just isn't that simple. Berry also told me that he fears any hedge would "disrupt the Gambling Gods." Look, I get it. In my younger years, I believed changing seats on the couch helped me win a bet. I also have convinced myself that I can jinx a bet. We all feel we are part of the process. That's also what being a fan means and what led Berry to this situation: a fun, throwaway bet on his favorite hockey team while visiting Vegas for a work conference.

Only Berry can make the decision to guarantee money with a hedge or go for it all with his favorite team. It is fun to imagine the hypothetical but we never truly know how to behave unless we are in that exact scenario. Emotion plays too big of a factor. Berry knows this.

He also knows it's a darn good dilemma.