Dealmaking when you have a chance

[Hal 2000]

Live $1k freeroll w/ $40 rebuys + add-on. $2440 total in the pool. Down to 6 of us. Without a deal only top 4 would have cashed here. One guy's in front by a mile, so the deal proposed was for him to take $1100, and we whack up $1340 among five of us. One kid, barely looked 21 and clearly had never been in this situation, says he wants to keep playing because he's got the most chips out of the five of us. He had about 18k, and were at $100 ante, 1k/2k blinds. Rest of us have anywhere from 10-15k. BIIIIIG advantage, right?

So, since he doesn't want to do business, we keep playing. Newbie then promptly gets all-in with JJ against 1010. Other guy spikes a 10 and newbie is down to about 4 or 5k.
He predictably responds with "Now I'll do a deal" Picture laughter from 5 players and 20 or so railbirds.
Long story short, the greedy punk cost himself 70 bucks of his share. Looking back we should have let him get eliminated and then made a deal.

[Shoe]

Why would you rebuy for $40 in a freeroll, am i missing something?

[Bremen]

Same reason you would normally rebuy?