I think signing JD would squeeze HRam out of the option, unless there's an injury to Moreland, JD or an OF'er.
I realize arb raises will be costly over the next few years and will alone eat up much of the departing players' contracts lost, but we may not need to add much to the roster, except to resign or replace Kimbrel and Pom in kind.
Timetable on future Sox free agents:
After 2018:
$22M Ramirez
$13M Kimbrel
$8.5M Pomeranz
$3.8M Joe Kelly
After 2019:
$20.5M Porcello
$19M Pablo
$13.5M C Sale
____ Bogaerts
$6.5M Moreland
____ Thornburg
____ B Holt
If we can pay all arb raises with HRam's salary, we can probably have enough to keep Pom OR Kimbrel. Losing one will not make us noncompetitive. If Henry does not mind keeping us over the second penalty level for a second year in a row, we can probably keep both and not go over the third penalty level.
After 2019, losing Porcello and his contract might not be too bad. His money plus Sale's $13.5M could help us keep Sale. We may lose Bogey, but I think losing Pablo's contract can help us keep Bogey and pay the arb raises.
It's after 2020 that keeping everybody and facing a third consecutive over the tax limit penalty will be the true reckoning time, IMO.