First, let me state that this was a 3000 person freeroll on RV - I would not normally be so risky on a hand like this. But, considering the circumstances, I thought that it was worth a shot.
Not even close to the money yet and I was getting short stacked. I was on the big blind, which was, I think, $100 (maybe $50), but after the blind I was down to around $550 and had not been catching any cards. There were a few biggish stack at the table, ranging from $2000-$4000+, the rest were maybe $700-$1500. Table was pretty passive, except for one or two of the larger stacks, but even they weren't too aggressive.
I'm dealt Kc2c on the BB, about 4 callers, I check.
Flop is something like 245 (might have been 235, but that's not an issue), with one club. I go all-in for around $550 to start the betting
Here's the thought process:
1) It's a freeroll
2) While I only have bottom pair and good kicker, the chances of the other callers pairing the board, in my opinion, were rather low (SB had folded, I think), so I could already be leading.
3) Outside chance at a flush, but that wasn't much of a consideration.
4) All-in move could signal to the table that I have a straight, two pair, or trips, especially since I got a free look at the flop. Thus, I could force everyone to fold.
5) If anyone does call, there would be a good chance that they just have high cards, like AK or KQ, and think they have the best hand with the rag flop.
Result: all but one fold, who has 99. Turn was another club, so I had 14 outs on the river, but I didn't catch it and went out at about 1000th place. Turns out, if the guy did just have high cards, as I thought might happen, I would've won, as nothing hit the board above an 8.
Again, I would not make this move in a real money game, but considering the situation, while it was risky, I don't think it was all that stupid. Points 4 and 5 above were the most important in my thought process.