Will Bad Bunny Wear a Dress? Here Are the Strangest Super Bowl Event Contracts

Set, hut!

Football season is almost at a close, which means bets on the Big Game are skyrocketing. Analysts expect viewers to wager approximately $1.76 billion on this Sunday’s Super Bowl LX, a nearly 27% year-over-year increase. New prediction markets from firms like Polymarket, Kalshi and now Robinhood are offering bettors the opportunity to take increasingly niche gambles on everything from which companies will run ads during the event to what words might be spoken by the announcers. (Event contracts for the latter from Polymarket include “underdog,” “concussion” and the phrase “Now, here’s a guy.”) Should advisors be concerned that their clients might be parlaying their 401(k)s away?

“We have seen a rise in this in our younger clients, aged 20 to 40 years old,” said Kyle Mostransky, CEO of investment management firm Mostransky & Associates. “Our concern is that this leads into crypto speculation, meme stocks and treating investing as picking winners and not owning businesses.”

Banking on It

Apps like FanDuel, BetMGM and DraftKings capitalize on the legal sports betting industry — estimated to be worth more than $10 billion — by offering real-time wagers on everything from football to darts. These apps can blur the line between skill and chance, Mostransky said, which encourages younger, less experienced investors to buy in. It’s also bleeding over into the world of investing. “I don’t see an issue with a big event like the Super Bowl, putting $100 on a box or doing it for charity,” said Larry Sprung, founder of Mitlin Financial. “But when people are betting on how long the national anthem is going to last, or how long the coin flip is going to take, I think it’s crazy.”

Advisor Upside decided to undertake a serious investigation into some of the strangest Super Bowl-related contracts on the market as of Wednesday afternoon, including:

• The color of the Gatorade that will be poured on the winning team’s head coach. (Orange was the most popular option, at 25%, although yellow is clearly the best.)
• Whether halftime show performer Bad Bunny will wear a skirt or dress during his performance (15%).
• Which celebrities will attend the game, with the top three bets being former New England Patriots quarterback Tom Brady (99%), Amazon founder Jeff Bezos (60%) and singer Justin Bieber (56%).

To Parlay or IRA? Ultimately, rolling the dice on sporting events is up to the individual, even if it might not be the best long-term financial decision. But advisors should still know when to put their foot down, said Joon Um, a financial planner with Secure Tax & Accounting.

“When we step in is when betting starts creeping into money that should be earmarked for savings, taxes or long-term goals. Then it becomes a planning issue, not a lifestyle one,” Um said. “Being based in LA, we also have plenty of clients who enjoy Vegas trips, so we frame betting the same way: entertainment spending with clear limits.”