Looking at the payroll vs. production right now, and it is stark to see that, by and large, the guys cashing big checks have been the biggest disasters. Here's their salary by player this year:
Ramirez: $19.8M, -0.9 fWAR
Sandoval: $17.6M, -0.9 fWAR
Napoli: $16.0M, -0.2 fWAR
Ortiz: $16.0M, 0.4 fWAR
Victorino: $13.0M, 0.2 fWAR
Porcello: $12.5M, 0.0 fWAR
Castillo: $11.3M, -0.5 fWAR
That's $106M in payroll producing -1.9 WAR collectively - and this doesn't even factor in Masterson or Craig just collecting paychecks for zero or negative production to the MLB team. Just an astounding misallocation of resources. The good news is that the guys producing are the ones on attractive contracts. Betts, Bogaerts, Holt, EdRod, Miley, Pedroia and Buchholz (pre-injury) were all on either below-market deals or still are still pre-arbitration.
In some ways, this is a good problem, as you want your young guys being contributors. In another, it's a real challenge, as moving big salaries with 3-4 years left on a deal will be a tough pill to swallow. There's not a lot of teams that can or will stomach a $20M+ commitment for a mediocre veteran player - unless AJ Preller wants to start wheeling and dealing again.
Bottom line, the team needs to clear the flotsam and jetsam. Napoli and Victorino will solve themselves soon. Ortiz has already said he's not going anywhere, so there's not much they can do there. The real issue lies in the most recent signings. In order for this team to get righted, the organization has to figure out what to do with Porcello, Castillo, Sandoval and Ramirez. It will likely require eating a big chunk of one of these deals to move on, and also require someone (likely Porcello or Castillo) bouncing back to be solid contributors, but they need to find a way to clear out payroll and roster space. They just cannot make improvements to this team if they're going into 2016 with over $100M committed to guys playing at or below replacement level, even with guys like Betts, Bogaerts, and EdRod basically playing for free.