Nick, this is where the attrition game comes into play. If Henry parlayed contracts like a Steinbrenner, then so be it. You cannot create a window with money alone nowadays. You need to use your farm to either deal for top notch talent or develop it. Ben and Theo developed the talent. Dan used it to create this monster of a club. Every single good team will have attrition. Other teams pull away from the super team and the price rises and teams fall. The sox peaked and won a title right smack in the middle of their window. They've got one more year before the pain sets in.
Bogaerts is a very good player. There aren't too many 5 WAR players out there. He has been close to 5WAR now in 3 of the last 4 seasons. His first season of his next FA contract will be entirely as a 27 yr old. His age, production and position will be huge for determining his contract. He could conceivable get an 8 yr deal and be prime level for 6-7 of those years. He is gonna get huge money. And while you think his loss will be mitigated by keeping the other players, remember the construction of your lineup. When you have JBJ, Vasquez, and Nunez at the bottom of your order, are you willing to have another minus offensive producer in Xander's place? Also, I know JD changed your lineup, but when he opts out after 2019, he will be 32 years old. Do you offer another 5 year deal at big money to a DH knowing he will not be worth it maybe even a year or two into the contract? I honestly think DD will sign Xander no matter the cost and will thank JD for his time here, offer a QO and let him walk