When your team is the New England Patriots, it’s easy to be overconfident about their chances at the Super Bowl. They’ve been to The Big Game a record ten times, won the championship five times and are led by perhaps the greatest quarterback of all time in Tom Brady. On paper, Super Bowl LII looked like a steal as they were facing the ultimate underdogs – the Philadelphia Eagles, led by backup quarterback Nick Foles.

So you can’t blame Barry Lipsett, president of Top 40 supplier Charles River Apparel (asi/44620), for making a few bets with clients and sales reps. He does a lot of charity work in the Boston area and had a firm belief in his team. His company joined the fun by offering $1,000 to any customer who correctly guessed the final score. Even though nobody did, Charles River still sent sweatshirts to all participants in their favorite teams’ colors.

Unfortunately, Lipsett was way off on the final score, as the Eagles made history by winning their first Super Bowl championship. A man of his word, Lipsett bought an Eagles T-shirt, ordered some Philly cheesesteaks and tasted defeat in epic fashion. He also shipped out a few Eagles sweatshirts and New England fried clams to the victors.

At the risk of rubbing it in, maybe next year he can come down to the City of Brotherly Love and eat a true cheesesteak.