In case you haven't noticed, the Red Sox have a new head of baseball operations—one David Dombrowski. Given his past behavior, he's not exactly 'a riddle wrapped in a mystery inside an enigma' (to quote Winston Churchill). Nevertheless, his situation here in Boston is pretty unique. This team needs: 1.) a stud at the top of the rotation and 2.) a completely re-vamped bullpen. They might also need a first baseman and (if Jackie Bradley, Jr. or Rusney Castillo are traded) another outfielder. Will 'Double D' double-down on the kids and look to build a contender from within? Or, will he go for broke—signing a bevy of free agents like Chris Davis at first, Alex Gordon in left and David Price on the mound? Or will he go with a mix of both approaches? Whatever he does, he will be facing an increasingly angst-ridden fan base that has seen three last place finishes in the last four years—albeit with a World Series Championship thrown in for good measure. The problem is, expectations now call for championships as the norm not the exception.