I thought it was weird last winter when trading Porcello wasn’t more widely supported on this board, but it’s entirely possible that DD explores it and found no takers. Not many teams were adding pitching (or trying to win), and there were a lot of guys available cheaper than $20M.
But I agree with you that of course it was the right move, though I don’t think turning around and giving that money right back to Keuchel would’ve helped much.
No one wants to break up the band after they go platinum. But some times you need to make little changes to ensure continued success. Maybe Keuchel wouldn't have helped much but he would have been better in that 5th spot than what they've been running out there if they'd signed him in the off-season and just ate the draft pick and he wouldn't have cost that much per season, so they would have had extra money to play with to make another signing (or two) that would have bridged the gap.
I doubt it was explored because there would have been takers, especially when teams lost out on the big name free agents and especially because he's a CYA-winning pitcher who won 20+ games as recently as a couple of seasons ago and has "big game" experience. You could make the argument that Keuchel offered much of the same for less money and "only" draft pick compensation but teams always seem more willing to trade than lose draft picks for some strange reason. Why would the Red Sox want to give that up? The same reason they were willing to let Pedro walk: money.
If they thought this bullpen would be "good enough" without Kimbrell and Kelly (adding Wright and one of many kids), then getting rid of Porcello from the SAME TEAM THAT WON 108 GAMES AND THE WORLD FUCKING SERIES would have been met with wild disbelief and anger.
Maybe so, but as I said above, some times you need to make changes to keep things rolling right along. Of the three Red Sox championship teams before last year's title-winners, I can't recall any of them that came back EXACTLY the same the next season. More's the point, there were generally some pretty big changes. After 2004, Pedro left (for nothing) and they signed Matt Clement to fill the spot on the staff. After 2007, they brought back Schilling but he was not a contributor and so they got Bartolo Colón (who quit on the team) and Paul Byrd. After 2013, there were wholesale changes including losing Ellsbury, Dempster retiring (whether talked into it or not), Saltalamacchia leaving, and Pierzynski coming in. And while the 2014 squad was ultimately doomed, the previous two times saw the team go back to the playoffs.
I realize it's a different sport and the shelf lives of the players are different, but Belichick has made some shocking trades after successful seasons and very rarely have they come back to haunt him. Meanwhile, the Patriots have been in the playoffs almost every season and have won 6 titles out of 9 tries.
Porcello should have gone. Maybe Dombrowski tried, but I personally doubt it. Either way, it's always going to be a "what if" regardless of how the season plays out.