Usually, but not always, the holdout is one of the chip leaders who wants to take advantage of the bubble.
Allowing the "deal" to be made despite the person holding out is, in my view, collusion between multiple players, and should not be allowed.
Ken, I’m curious how the term collusion applies here? No one is conspiring secretly to gain an edge on another player. The players are being very open, and in no way did they mention anything about playing at that holdout player or softplaying eachother, nor did they show any animosity towards that player. I’m not saying you’re wrong, I would just like a little more elaboration on that.
Good question. Making me think about it more deeply...
I guess I never thought that collusion always had to be a problem with secrecy, meaning although a collusory act is usually a secret one it doesn't have to be. I think I've accepted "collusion" in the poker context as having a meaning more like "agreeing to act in concert against another".
This reminds me a bit of the debate about whether or not we should be asking that staking arrangements between players at a final table be disclosed. I guess part of that debate involved discussing whether a presumption that players who have that type of relationship with each other will softplay each other, or at least act in ways in which they really aren't playing as they might if they truly were playing "one player to a hand", because their goal is to act in a way that furthers their collective interests. Since those types of arrangements haven't (yet) been made illegal, then at least disclosing that fact would put others on notice and could allow them to try to protect themselves accordingly, presumably.
I think the act that you describe has some similar issues, but goes way beyond that. If everyone else has agreed to pay the bubble, the opportunity for someone to actually be that bubble has been lost. It's fine if everyone agrees, but if not everyone agrees, it's hard for you to convince the holdout person that everyone else is going to play exact the same way as they might if they were all playing "one player to a hand" on the bubble. I think that in effect they ARE targeting that holdout player and playing against them -- everyone else has acted as a TEAM for that particular decision, which will have a direct impact on the way the hand is played for all the hands after that which would have otherwise been "bubble" hands. So if it's not technically an issue of "collusion" in some books, I'd say it certainly is a violation of "one player to a hand" or some variation of that.
With respect to the insurance argument, I'd ask this... whose getting the insurance premium? Not the holdout, presumably. If they are desperate to pay out the bubble, would it be ok to pay the holdout something until he agrees? If I was the chipleader and the holdout, and you guaranteed me first place money, I think I'd agree to pay the bubble... ;-)
It's a difficult problem because I do see not wanting to give an incentive for backroom deals. But I guess if they do a secret deal, they risk disqualification, and the house is not involved. I don't know... it's not an easy problem. "We know that there's a chance that you might steal from this guy when he's not looking, so at least if you're up front and steal from him when he's looking, then we're ok with that and it won't be stealing anymore." lol