OK, I'll contribute to your Psychological exercise:
If Mr. Machado is still pining for the Yankees, then I'm over pining for him. If the Sox have actually offered him 8 years and $250 Million +, and certainly extended themselves in other ways to make him feel comfortable, yet he still doesn't want to come to the South Side, I'd be ok with just moving on. This team is not going to compete for the Division, in 2019, with Manny, even if they sign him. I'm personally ok with one more year of the rebuild and one more Draft, after this year's #3 pick. Therefore, I would suggest the following:
1) Trade Alonso and Jay, at the nearest opportunity, even if the Sox have to pay part of the contracts. Neither has any long term usefulness, on the contending team, starting in 2020.
2) Give the outfield corners' playing time to Eloy and Palka, who might also spend a little time DH'ing or spelling Jose at 1ST, while he DH's. If Palka hits enough, he could be a useful piece going forward, given his age and lack of service time. He might ultimately be a first baseman, or a DH. That left handed bat can always be useful, if he gets on base enough.
3) Let Engel start the year in CF, in order to shore up the questionable outfield defense. Once Luis Gonzalez, who is the oldest and probably the closest to Major League ready prospect, is ready, bring him up and let him vie for the position, until Robert is ready, in a couple of years. Monitor the progress of the promising corner outfielders, to see who might ultimately emerge as a viable candidate. Adolfo, Rutherford, Basabe and Walker all have a decent chance of developing into valuable pieces, but playing a corner, they need to hit. Gonzalez may end up moving to a corner, when Robert is ready, and having been brought up early could help to determine if his bat plays well enough for him to fill a corner OF slot.
4) Move Moncada to 3RD and give him a year to get comfortable there. Yolmer goes back to his natural position at 2ND, which he can very capably hold down until Madrigal is ready, hopefully next year.
5) Don't acquire any more veteran starting pitchers, but instead give the starts to the youngsters in an attempt to find out who can fill the rotation, behind Kopech, Cease and Rodon, starting in 2020. There are enough promising arms in the organization to fill the staff, starting with Lopez, Giolito, Hansen, Lambert, Banuelos and Covey. Fulmer may even finally figure it out. Hopefully, a few will emerge and take the pressure off the need to retain Rodon, on an expensive free agent contract, in 2022.
6) Save the financial resources to extend the younger guys, who will hopefully emerge as solid core pieces. Use the rest of the money to fill any holes which still exist starting in 2020.
7) Let's see which of our Minor League players take a big enough step forward, and begin to use that farm system capital as trading chips, after they have established decent Minor League resumes.
8 Mix the newly acquired, veteran bullpen arms with the best relief prospects, in hopes of sorting out who might be counted on to handle the load, starting in 2020. Guys like Burdi, Ruiz, Hamilton, Tyler Johnson and Fry might be good enough to make up the bulk of the relief core, after Herrera and Colome exit.
9) I don’t know what to think about catcher, as there is a good chance that the Sox could select one with their #3 pick, in this June’s Draft. If Rutschman is available at #3, I suspect that the Sox would grab him. Then too, it will be interesting to see what kind of year Langeliers has. If they take someone else, like Vaughn, then I assume that both Zevala and Collins remain the prime candidates, starting in 2020.
There, I feel better now. Thank you.