I am going to come out strongly in favor of the move to bring in Dombrowski. Looking at individual moves or even strengths and weaknesses of individual teams he's constructed misses the forest for the trees. He's built a winner everywhere he's been, and he's worked in different eras and under owners with different philosophies from win now to blow it up. The net of everything is quite positive, as shown by that graph several pages back, despite ways to quibble with its methodology. I'm sure he's well v, ersed in modern analytics and has the scouting background to know both what they tell you and, more importantly, what they don't tell you.
The biggest advantage is that he won't be emotionally attached to any of the players in the organization. He has also shown two traits that I think are key to building the pitching staff that this first-rate offense deserves. First, he's shown that he can properly value the future vs. the present in prospect trades. Second, he's shown that he clearly understands the Charley Finley maxim: "It's not signing superstars for big money that will kill you, it is signing nonstars to superstar money that will kill you. In that vein, I hope that one of the first things he does is discuss the "never acquire a pitcher over 30 on a long-term contract" edict with John Henry, and the second thing he does is explain why overpaying for Miguel Cabrera is very different from overpaying for Ric Porcello. Put another way, explain why "overpaying in dollars to underpay in years of commitment" is not necessarily a higher risk-return investment frontier--to put it in Henry's wheelhouse--than as any other strategy for acquiring top tier talent.
The second tier signings of Ramirez, Sandoval, and Porcello to first tier money, came from that edict, though to my knowledge there was no specific edict from ownership to sign those particular players this particular offseason. Thus, those decisions lie squarely in Ben Cherington's lap. In contrast, the hands of the Detroit owner are clearly documented in the long-term big money contracts handed out by Dombrowski. At least in the signing of Miggy, I remember without having to look it up a quote attributed to Illich along the lines of "I just can't imagine Miggy ever playing for anyone else."
So Bravo to ownership for recognizing there was a problem, and taking a bold step to fix it by bringing in one of the best of all time. If Ben Cherington truly had the oppportunity to work for Dave Dombrowski and turned it down, just add that to the long line of bad decisions he's made in the past 4 years. Even in 2012 with the brilliant house cleaning after they fell out of contention, he made many small decisions -- like trading Reddick plus for Bailey and Lowrie plus for Melancon -- that were questionable even without hindsight, and the failure of those transactions led to the need to punt the 2012 season.