So It would be hard to think of good questions for this because i dont know much of the lore around any of my teammates lol. But I think as far as what I would be going for, its clear: the formula was perfected by the late and great Norm Macdonald when he infiltrated an interview of Blake Griffin, and later done again by Mr. David Letterman. If I was going to infiltrate a presser to mess with my teammates, I would simply just ask them the dumbest fucking questions I could think of. Here i'll try and think of some

"I saw you broke a stick tonight on a slapshot, was that part of your plan?"

"Were you aware that the Turd Ferguson trophy is not actually a turd?"

"I saw the zamboni driver put on a terrible display in the second intermission, do you think he is at risk of being traded?"