Originally Posted by flyer85
What causes some GMs/organizations to make such high risk/low return decisions where the odds of a deal working in your favor over the entire contract are extremely small?
It's just the environment, and it's probably only going to get worse. Teams have cash to spend, but the more expensive free agents get, the more they'll want to lock up their own good young players as a countermeasure before they get to free agency. The supply and demand balance is out of whack. A GM either pays the inflated prices or he doesn't play, and in certain markets with certain owners, not playing is not an option.
Having said that, even in an inflated market some deals are dumber than others.