"That said, John made ic clear that there is a goal to try to get under the CBT in 2020. But he also said, and Tom followed up and clarified, that that is a goal but not a mandate.:

The Red Sox, whose payroll was around $240 million in 2019, face a difficult task in getting below the CBT next season. They have significant money coming off the books as some players depart for free agency, but Xander Bogaerts and Chris Sale are due raises with contract extensions that begin next season. There also are heavy raises in arbitration-eligible salaries due for some players, including Mookie Betts, who should make around $30 million next season.

J.D. Martinez also is unlikely to opt out of his contract that would pay him over $23 million next season, and the club is continuing to pursue a long-term extension with Betts.
- Boston Herald

So there's the situation. The Red Sox have a goal of getting under the CBT for 2020 and about $30M to shave from payroll. Despite some hefty dead-weight contracts coming off the books (hello, Pablo Sandoval), the salary increases across the roster are likely to erode their net benefit to almost zero.

Note: All values are in the AAV salary value used for calculating the CBT, not the actual dollar value due in any particular contract year.

Expiring contracts: $62.2M
Rick Porcello ($20.625M AAV)
Pablo Sandoval ($18.45M)
Mitch Moreland ($6.5M)
Steve Pearce ($6.25M)
Eduardo Nunez ($5M)
Brock Holt ($3.575M)
Tyler Thornburg ($1.75M)

Salary increases: $19.1M
Chris Sale $10.6M
Xander Bogaerts $8M
Player benefits $0.5M

Player options: $8.5M
Andrew Cashner $8.5M (Note: net payment by Sox in 2019 was 1.5M; 2020 option for $10M)

Arbitration projections: $12.25M+?
I'll update this as projections are posted in the next week or so.
Mookie Betts $30M ($10M)
Jackie Bradley $10.5M (2M)
Sandy Leon $2.75M (0.25M)
Eduardo Rodriguez
Matt Barnes
Steven Wright
Heath Hembree
Brandon Workman
Gorkys Hernandez
Andrew Benintendi

Net savings (before arbitration adjustments): $22.4M

The Red Sox could very easily decide that Andrew Cashner's 5+ ERA is not worth an additional $8.5M. There have been some rumors that they like Tanner Houck's progress a lot and that discussion surfacing at the end of the season may not be entirely coincidence. Without long ties to Fenway, he's low-hanging fruit that could be replaced from within.

The Red Sox need to talk Dustin Pedroia into retirement. Forget sentimental reasons to keep the dirt dog around or any crazy idea that he will come back a force: since the Sox bowed out of the 2017 playoffs in the first round, Pedroia has a total of 34 MLB plate appearances. With all respect due for his abilities, 2020 will be a season of reacclimation (at best) heading into his final contract season. Maybe let him be the infield instructor but get him off the roster.

Uncertain is the situation with JD Martinez. Even with lower-than-anticipated megacontracts last offseason, a WAR in the 2.0-2.5 range could approximate the $22M AAV that Martinez signed for in the spring of 2018. He's clearly demonstrated that his phenomenal 2017 season wasn't a fluke and it's not out of the question that he opts-out given the market. The hitters available this winter with a WAR above 2 are Yasmani Grandal (option), Anthony Rizzo (option), Anthony Rendon, Josh Donaldson, Mike Moustakas (option), Brett Gardner, Marcell Ozuna, Starling Marte, Adam Eaton, Nelson Cruz (option), and Edwin Encarnacion (option). Martinez is younger than Cruz and Encarnacion by at least five years. Grandal, Rendon, and Donaldson might be the closest competition on the market but they do not compete in terms of where they play. I think that the FA market contraction has most people suggesting that JDM will stay in Boston but I won't be surprised to see Boras read that competition as an invitation to at least get similar value ($22M AAV) for a longer period than the three years he has remaining. After all, it's no accident that he negotiated opt-outs the year after the big FA class from last year and into this (and next year's) market.

How would you go about cutting payroll while also fielding a competitive team in 2020?