He always gets it done, until he sets a team up for 5 years of failure and leaves... The Red Sox would probably still be bad had the Dodgers not bailed them out for some unknown reason. The Red Sox won a World Series the year after the bailout with essentially the same roster minus the bailout guys. It was a bit of a fluky thing (both being good enough to win it all in '13 and a sub-70 win team in '12), but I think that they'd still have been fine sitting on a pile of dead money with Carl Crawford. A-Gon would've been fine for a few years, Beckett was injured but his money would've been gone 2 years later. They basically only added Napoli and Shane Victorino in the stead of those guys the following year. You could argue they'd have struggled to bring in the next era of guys helping them sitting on Crawford, Gonzalez, Beckett, etc. but I think Gonzalez would've had some good years, Beckett was OK Any GM of a big market when offered the idea of: "well, you could sign Carl Crawford to fill this hole in our organizational system or you could trot out some subpar prospects" will take the big money deal eventually. Friedman is about as good as it gets as avoiding that and he's going to sign some big $ guys this offseason. The Red Sox are dominant and they are sitting on a gigantic pile of dead money again. The Dodgers have been a force since bailing out the Red Sox, both the high payroll and lower payroll versions have been. It's not so taboo for big markets. You run the risk of eventually having a bad year if you're a mega market like LA/Boston(salary-wise they are)/NYY, but all of these teams are sitting on $50 million in guys that aren't playing. The Dodgers have been on a bit of an austerity run the past few years but they're going to probably have some decisions coming up soon.