Here's the outfielders Boston has under contract for next season; Yoenis Cespedes, Shane Victorino, Rusney Castillo, Allen Craig, Daniel Nava, Jackie Bradley Jr., Mookie Betts, and Brock Holt. You only play 3 outfielders at a time - so having 8 seems a bit much. Even if you say Brock Holt and Mookie Betts are really infielders - that still leaves 6 outfielders for 3 starting jobs. Something has to give.
Meanwhile - here are the starters that are under control for next year; Clay Buchholz, Joe Kelly, Brandon Workman, Rubby Del La Rosa, Anthony Ranaundo and Allen Webster. Does any of those names jump out at you as a number 1 or 2 starter? Me neither.
So what to do? The obvious first answer is to sign Jon Lester to a long term deal. At this point 6-years for $150 million is what it will probably take. Then you hope Lester is more like Andy Pettitte when it comes to durability and less like Jack McDowell.
Even if you sign Lester - a rotation of Lester, Buchholz, Kelly, Del La Rosa and pick a name doesn't sound like a playoff contender. Signing free agent James Shields would obviously help but what are the odds of one team signing 2 of the top 3 free agent pitchers? That's why a starter is probably the number one trade priority for the team this off-season. The most obvious name would be Cole Hamels who is owed $94 million over the next 4 seasons.
The good news is that the class of free agent outfielders this year is pretty weak - and guess who has outfielders to spare? Pretty sad but I'm looking forward more to the hot stove than to the rest of the season. I think many fans feel the same.