Intentionally not catching a pop up happens quite often in baseball. They do it even with one person on base. That usually happens when a batter attempts to bunt a runner over, but pops it up. The runner notices the pop up, and quickly rushes back to first, and the batter takes his sweet precious time getting out of the box (think of barry bonds). If the pitcher (or whoever fields the ball) is savy, he'll seriously take note of where both the runner and batter is before deciding whether to drop the ball or not. I've seen Greg Maddux do it numerous times on TV.
What about pool (lame attempt to keep this pool related)? What if you have an automatic loss of game if you commit an intentional foul? Intentional fouls are tactical and part of the game. Same with dropping a ball in baseball.
Okay, i'm done participating in the hijacking of this thread.