Well in most cases other than Benning somehow, the GM who signed the deal is fired and the next guy gets to deal with it. This whole, "nobody forced the GM to offer those deals" is looking at it entirely from a punitive standpoint and is not looking at what is good for the team, the league, the players, or the fans. How on earth is the Skinner contract in any way good for the league? Yeah, the GM is an idiot, but watching a franchise wither away and lose passionate fans is a losing proposition.
Looking at the Skinner and Bobrovsky contracts it's hard to imagine things getting even worse. But frankly, the GM who makes a $50m mistake gets fired. As the other guy pointed out, owners don't want to be pissing money away on compliance buyouts. If you screw up that badly with your owner's money, you should be getting fired anyways. I just don't see why a franchise needs to piss away the years of good players like Eichel, or watch a star goalie like Markstrom walk out the door because their idiot GM signed some boneheaded deals. The Oilers have wasted prime years of McDavid and Draisaitl because Chiarelli f***ed up and it's an absolute nightmare for the league. The Salary Cap is meant to promote parity, it shouldn't be costing teams years of relevance.