You know....once it's an "Official group ride" the liability deal goes through the roof. That's why on our annual MINI event, our local club makes darn sure to note MANY times that it is NOT an official club event and that we are just a bunch of individuals gathering together for a spirited drive.
Then the fact that they specify how the group is supposed to ride...if it's found to be unsafe...and something happens, ka ching!
Riding with Nice Rumble and the Seacoast Sport club
they had everyone sign a waiver before the ride absolving the club of any responsibility should something not go well. They ran a pretty good pace and almost always had at least 1 or 2 bikes unfit to ride home by the end of the day.
If well drafted (typically means it's really an express assumption of a well defined risk, a covenant not to sue, and an indemnification and hold harmless agreement), that kind of "waiver" will usually hold up against others who have signed it . . . for their own injuries. But against a pillion who has not, a bystander who has not or another motorist who has not, it is almost certainly ineffective no matter what its terms might say -- those victims are not bound by a document they did not sign. So, if they're injured and any fault for the accident is traceable to an unsafe group riding practice, especially if it's enforced by the group or someone in it, it's possible that liability might be extended beyond the individual rider who actually had the collision that caused the injury.
Usually, an individual rider's own negligence is the only proximate cause of an accident. And his own decisions and actions while riding in a group do not make the group liable. This ***-clown ride captain's directions to the group, combined with the president's enforcement of those directions are what make them potentially subject to liability. A little tougher to bind the rest of the group, but not out of the question, especially if some kind of mutual group-think** enforces a dangerous behavior that proximately causes an accident.
Anyone can sue over most anything. Who has sufficiently deep pockets and how bad the injuries/damages are have direct relationships to the likelihood of suits against those whose liability is more remote. Most of the time, we don't really have to worry about those things in "ride your own ride" group destination rides. But insisting upon a dangerous practice and enforcing it is STUPID. Run away before any gets on you!
** And your friend getting his *** chewed by the group for agreeing with your concerns is exactly the kind of thing lawyers are interested in exploring in that liability game of "pin the tail on the rest of the sheep." ******* idiots!