The Most Dickish Thing I've Ever Done (But It Was Hilarious)

I recently went to Atlantic City for the PokerStars Festival, a series of tournaments meant to promote poker now that PokerStars offers online play in my home state.
Because Resorts, which partners with PokerStars, doesn't have a poker room, the tournaments were held in a ballroom. As I walked through the tables I saw some well-known players sitting amongst regular folks aka amateurs.
I also recognized a friend of mine, Andy, and on his direct right was Barry Greenstein, peacefully reading news articles on his iPad.
I noticed Andy, whom I had never met in person, only online, was wearing a tank top that said "If you're offended, I'll help you pack" and had a big American flag in the middle.

Turns out two other friends (I use the term loosely) paid him $100 each to wear the shirt the entire day. As I was being told this story, I was inches from Barry Greenstein who looked up at me, and then I said:

"Barry, they're paying him $200 to wear this shirt. How much are they paying you to wear that sweater?"

Luckily it was well-received and when I saw him sitting alone later (he remained at his table during a break) I went over and apologized and we had a good laugh. He took it very well. And then we briefly talked about politics. He couldn't have been nicer. And I couldn't have been more dickish.