Justin Thomas And Smylie Kaufman Had An Epic Flip Cup Game With Sidney Crosby And The Penguins

red and blue Solo cups


It’s typically pretty difficult to play a sport for a living if you don’t have a fierce competitive spirit, and it’s not rare for professional athletes to adopt a “Win At All Costs Mentality” in a number of different areas in life.

That reality is manifested in the many, many stories that revolve around Michael Jordan gambling on the golf course, and it was also highlighted in a tale that was shared by a couple of guys who’ve done pretty well for themselves on the PGA Tour.

Justin Thomas recently sat down for a lengthy chat with Smylie Kaufman on the debut episode of the latter’s new podcast, which included a segment revolving around a pretty wild saga that kicked off when the two men found themselves eating at the same restaurant as Sidney Crosby.

The night in question unfolded while Thomas and Kaufman were on the latest iteration of their fairly legendary annual “Spring Break” trip and ran into Crosby and a few members of the Penguins, who’d also taken a yearly golf vacation on the earlier side after missing the Stanley Cup Playoffs.

Thomas detailed an amazing game of one-upmanship that unfolded after Crosby and Co. sent a bottle of wine to their table, as the golfers responded by asking the waiters to split a Caesar solid into eight tiny portions for the Pittsburgh crew (they received a bunch of shot glasses rimmed with salt and filled with warm water in return before retaliating by sending them shots of 2% milk).

Both squads eventually discovered they’d rented houses right across the street from each other, and they hung out a bit before deciding to play a game of flip cup.

Thomas recalled what transpired during that showdown, saying:

“Our immature childish side takes over. We’re having fun with them, and naturally, the boys are like, ‘Let’s play some flip cup.’

I’m all pumped up. I’m on Sidney Crosby’s flip cup team. Like, this is going to be awesome…

You and Sid were facing off last. Our team was just embarrassing. Potentially the worst exhibition of flip cup I’ve ever seen in my life. It gets to Smiley and we’re literally on our second or third person. Everyone on his team is like, ‘Smiley! Go! What are you doing?’

He’s just hands on his knees looking at Sid, waiting; straight up staring the captain right in the eyes, waiting for him to go. So finally, I go, I finish, and Smiley’s just holding his cup looking at Sid like, ‘You ready?’

Down, up, down, one swing, one flip, done. Game over just like that. It was one of the most baller moves I’ve ever seen.”

That’s a story you tell to your grandkids.