Having a good team is the sexiest way to kick off baseball's winter season. Your team and your fans have visions of pennants dancing in your heads, and the free-agent market looks like a buffet of awesomeness as you think about what big-name signings and acquisitions would make your good team into a great one.
But when you're an also-ran, the options are less exhilarating. A big signing may just make your non-contending team more expensive. A rebuild job may be a smart decision, but the moment you decide to start tearing up your team can be heart-rending and won't sell tickets for next season. These decisions need to be made one way or another, and frequently these will make up the turning points that decide if your team will someday become the 2016 Cubs or the 2016 Padres.
With that in mind, how have the bad teams in baseball done so far this winter? For each of these teams, 10 games out of the playoffs or worse, let's look at what they needed to be doing this winter, and how well they've accomplished that goal.
Arizona Diamondbacks (69-93)
The Mission: Rebuild the front office.
Arizona probably had a worse season than you'd have expected from their talent, but even if the team had gone 82-80 and missed the playoffs by a less nauseating margin, the same fundamental problem would have remained. Simply put, Arizona's front office was not remotely up to the challenges a modern front office deals with. Just stuffing an old player and an old manager into a front office and letting them throw some money around is, as plans go, a thoroughly archaic concept. Horse-drawn carriages were once an efficient method of transportation, too, but in 2016 they're more for romantic sojourns in Central Park, not for competing with tractor-trailers for shipping goods. To get where they're going, Arizona first needed to figure out where they actually are. And that's what they did, snagging one of the top GM candidates in Mike Hazen from the Red Sox. They also brought in Amiel Sawdaye (also from Boston) and Jared Porter from the Cubs to fill out the front office. Good moves, but their work is now just starting.
Chicago White Sox (78-84)
The Mission: Take apart the core.
The plan in Chicago had been simple: Add enough through free agency and trades to supplement a recovering farm system and make a few serious runs in the AL Central, one of the weaker divisions in baseball. Unfortunately for the White Sox, the pieces never came together, they never finished .500 with Jose Abreu or David Robertson or Melky Cabrera or Todd Frazier or Adam Eaton, and players like Chris Sale and Jose Quintana only got the briefest taste of winning early in their careers. Even if the plan was good -- I'd argue it was, though the execution wasn't always -- at this point it's just not happening. Chicago had to accept that their window was just about closed, and they had to get while the going is good. After all, the longer you wait to rebuild, the more painful it is because your tradable assets may have lost value.
And they did it! The plan isn't complete yet, but you don't trade Chris Sale and Adam Eaton as they did if you plan to just tinker around the edges. They may have varying ideas on the optimal way to get value out of Quintana, Robertson, Frazier and eventually Abreu, but there's no doubt that's the plan. Trading just two players so far, the White Sox already have a top-five farm system. The White Sox could end up with the best farm system they've ever had, or at least as far as I can remember.