It's fine to have it as a goal, but as I say, the man considered by many to be the one of the best GM's in history only did it once in 9 seasons with us.
Amazingly enough, the Red Sox only won the division once under Theo in 9 seasons, and it was in his 5th season.
I don't think winning the division is necessarily the real barometer of success.
It's a beautiful deal, really. Whitlock gets financial security, the Sox potentially get a bargain, and have a lot of control with those 2 team options and low buyouts.
Nice work by Bloom IMHO