OK - I'm down with being courteous and all ... but is the small fishing boat really a burdened vessel such that he no longer needs to yield ROW to a sailboat? Note that the poster said the fishing boat was under way - not anchored. If the boat in question was moving and it was impossible to tell that the guy was trolling anything until too late, I wouldn't feel that bad about having snagged a line...certainly not $250 bad. Based strictly on the information presented here, I would offer him to split the cost of the rig and if he didn't like that, I would offer to file a claim with the waterway folks and let them decide (DNR, Coasties, etc.).

Secondly, if his poles were so poorly restrained in the boat, what the hell was he going to do if he actually hooked a fish? That guy is likely at home laughing with his buddies about how he got $250 out of that sailboat guy (in front of his kids).