PR might be part of the reasoning, but I think we make a legitimate offer to Betts, this winter, that is fair and generous. If he takes it, great. If he refuses, there will be no Lester-like debacle. To me, the main reason for making a solid winter offer is to know whether we should trade him or not. If he turns down what we think he's worth, it makes sense to trade him, even if maybe that offer would have turned out to be the highest, and we'd have gotten him anyway. Besides, nothing will stop us from offering the same deal after he becomes a FA.
The Sox have a long history of accurately valuing their own players at the time the reach or near free agency, with the exception of Lester and maybe Lackey.
I'd like to see us be a good team, next year, but I'd also be okay with hastening the return to glory by maybe trading away a piece or two to brighten our extended future.
If we reset, I can't see us having a good chance at winning it all in 2020. I'm not saying we can't. We still have a solid core, and if health is on our side, we could look more like the 2018 Sox than the 2019 Sox, but my guess is, we wait until the deadline in 2020 to decide on trading JD and/or Betts and Workman. We may even look to trade players that will be FAs after 2021: ERod & Barnes, if we are already dismantling the team.