Long contracts are not ideal in isolation. Of course, from a buyer side, you'd like to go transaction to transaction. But we know the practical limitations. Long contracts are sometimes necessary to win an auction - and you have to evaluate whether the end state of the deal is acceptable. The Pedroia deal for instance, you know at the end of it he is not going to be an All-Star, but if you think he can be an average-below average 2nd baseman, the salary (taking into account baseball inflation) is pretty reasonable. (not a bargain, but not a ripoff) I was in favor of a long Lester deal because I thought his stuff aged well enough that by the end you'd be paying $27M for a durable low-end #3, which is still a useful guy. The administration's general belief I think is that longer deals are better bets for position players than pitchers, which is certainly sensible and true, but there are no absolutes.
Seeing Cherington's work here as something a bit more complex than good or bad, a devotee or a hater - is also sensible, but clearly some of the angry posters on the topic have a bit of "Hulk Smash!" in their thought process. The biggest mistake Cherington administration made was wussing out on playing the children. Letting Ellsbury walk because you had Bradley did make sense - you knew you were not getting 6 wins out of Bradley, but you also knew that Ellsbury was a very very low likelihood to be that too. What did NOT make sense was signing Grady Sizemore's broken down, past sell-date body and then giving him a starting gig over a spring's worth of at-bats. Moving Bogaerts off of shortstop was another of those things too - although that was a little more sensible seeing what a wasteland 3B was, and Drew was a good SS for us in 2013 - but still skittishness that the kids would not all turn into Mike Trout at-once. AJ Pierzynski was another - although there were sound reasons for keeping Vasquez on the farm. The team has an elite development machine, let it do its thing and be confident in your own evals.
I mean, you look at the last few weeks and the team has shown some life. It's fun - the kids are working through things which can only be learned at the big league level - and you get some information. Now, a team like Boston can afford to only want their premium guys playing for the big club - instead of Tampa who needs farm kids of all stripes to be affordable at all - but go ahead and play them. This was something Bobby Cox did to great effect in Atlanta, and something Epstein and Francona knew how to handle as well. (the best example being staying with Pedroia despite how overwhelmed he was when he first arrived)