I've never played in any tournaments with prize pools that large (I've only been playing since May), but I do remember my first $5,000 freeroll.
I played that tournament in July. There were 383 people entered in the tournament, top 50 spots paid. I was pretty nervous, but my wife got me a beer so I wasn't in too bad a shape to play.
Anyway, I got really lucky and managed to sneak into the money with very few chips (I had about $3000 and the blinds were at $250/$500). I was now on my second beer and both a friend of mine and my wife were watching me play.
And that's when it happened: I started "table-skating" (or "table-surfing"). I don't know if the term exists, but I started getting moved from table to table, being placed in position that guaranteed me at least 7 or 8 hands before the blinds would hit me. This happened over and over and I managed to skate my way down to 24th spot. I was now guaranteed $50 (pretty good for a freeroll).
I then played my usual game and managed to hang on to hit 17th spot and a $100 payday. Considering my bankroll was only at $300 at the time, I was pretty happy.
I then went on to have a few more beers and won a multi-table SNG at
Royal Vegas Poker for $16 more.
K.