The good thing about having to pay certain guys is that we can. Not a lot of teams will even approach a 189M payroll like the Sox will...And be willing to go over it. Soon the LT should be at or around 200M.
You have to trade young prospects sometimes. Its just part of the game. Even really good ones depending on whats going on in the organization. The trade has to be whats best for the organization. The Goal for every organization regarding trades is to get the best possible value back in return. DD seems pretty good at this. Kimbrel has been a good move. pomeranz was needed and looks to be a good/smart move, even if Espi works out. Bringing up Benintendi. Holding on to certain prospects/young players. Good draft getting Groome. So Id say hes done really well so far overall.
I didnt like that they didnt sign Lester to what couldve been a 22M/5-6 year deal at the time. He is still going to be worth what the Cubs gave him into his mid 30s IMHO. I think Price has adjusted to his new team and will end up earning his pay. FA is always going to cost more, so 30M is fair for an Ace is todays MLB. Thats why locking up Lester was so important. We probably couldve had Lester and Porcello for 42M rather than 50M with Price. There is always those certain vets that your going to have to pay, including your own home grown talent when/if the time comes. Eventually your going to have to pay some of these guys. Thats just part of it. Unless your the Rays or Athletics of course. But were not
The trick is to identify those in your own system and lock them up early if possible and your payroll allows.. Not all moves/deals will work out. But Between good drafting, development, trades/FA, and also figuring in injuries and underperformance that always happens, theres a lot going on for a Prez of Baseball ops and a GM to juggle. Theres always going to be deals that go wrong and prospects that dont work out, etc. you just have do more good than bad. Not easy, but I like who we have in the FO running thins right now.