From reading the replies and related threads, I think I have got what I was looking for. In general, it appears that a properly worded waiver can protect someone from liability if the person exhibits a reasonable duty of care and is not a total jackass. However, if the person exhibits gross negligence, then they can be held liable. The key being gross negligence.
IANAL but something I know for a fact is that anyone can file suit against anyone else in the US for pretty much anything. That in no way gaurentees the suit will win in court, but there you go.
What your friend needs to ask is what he wants to win from the triathalon organization. They have an interest in making him happy regardless of their legal responsibility. A suit can be costly and result in bad press even if they win.
If I were one of the organizers, I would be trying to negotiate a discount on a new bike for the guy, maybe offer a manufacturer a free mention if they replaced his wheels. I’d also see if the volunteer’s car insurance would cover the damages, and offer to join the victim as a friendly witness on his side in case he decided to pursue suit against them instead. I’d also waive his entry fee for the next year None of this would I do because of any legal responsibility - do it because it’s the right thing to do for a guy who undeservedly got nailed.
If your friend wants that kind of support, he’ll probably get it. If he wants to sue for millions, well, good luck with that.
None of this would I do because of any legal responsibility - do it because it’s the right thing to do for a guy who undeservedly got nailed.