Cherington had a 5 year plan or long term vision, similar to what Theo did with the Cubs, but not as extreme. He was building a strong farm while trying to stay competitive. In 2013, he did a great job of adding pieces without sacrificing the farm. In 2014 and 2015, not so much.
During Cherington's years here, the young core and the team as a whole were not yet at the place where it was time to 'go for it'. When Dombrowski took over, it was time. Cherington was not given the opportunity to see his vision come to fruition. Henry became impatient and panicked. Dombrowski is reaping the benefits of Theo's and Cherington's hard work.
Had Cherington been given the opportunity, I am positive that he would have made some moves and am positive that the team would have made the playoffs. I am also positive that we would not be falling of the cliff in 3-4 years.
No, I am not a fan of Dombrowski's team building philosophy. That said, if we win a championship or two in the next 3 years, I will happily take back everything I said.