So, here's what I think may happen.
First, I think the Ms will soon trade Edward Encarnacion, probably to the Rays, for more prospects. Hopefully Colin Poche will be one, and he will become the closer apparent. Any others will become immediate chips for the next move.
With Encarnacion gone, I think the Ms will trade with the Yankees again, getting Sonny Gray and Jacoby Ellsbury for, say, Ryon Healy and, probably, Ian Miller or Josh Stowers, and/or someone like Max Povse or Matt Festa plus international spending allowance room. The Ms are really running out of chips unless they make this a 3-way with the Rays with the return for Encarnacion going directly to the Yankees. The Yankees will want to save face with their return, but I suspect want to get rid of Ellsbury's contract enough to let Gray go too, similar to the way other dump trades have gone this year. And Healy may be better than Luke Voit or Greg Bird, even coming off a bit of a down year. The Ms will go ahead and use Ellsbury as the 5th OF, DH, and clubhouse leader, with the hope he will be attractive at the trade deadline to a contender.
Then, I think that almost inevitably, Kyle Seager, even with his "poison pill" extension, will get traded to the Padres for Wil Myers. If traded, Seager is owed $72.5M. Myers is owed $73M. The only difference is loading - Myers contract is to 2022, but is only $5M in 2019. Kyle's is also to 2022 with the extension, but he is owed $19.5M in 2019. Their career offensive performance numbers are remarkably similar (0.768 OPS for Kyle, 0.765 for Myers), but Kyle can play 3B well, which Myers cannot. Myers is 3 full years younger than Kyle, and may still have some ceiling left at age 28. The Padres, though, are openly after the best 3B they can find -- and, in spite of age, Kyle is that, and probably will be for the rest of his contract.
I also suspect the Ms will try to do a package deal with Seager and Leake, like the rumoured Segura-Leake for Myers+ trade discussions earlier in the off-season. Gray will take Leake's spot at the top of the rotation in any case. The Ms will pass on the money from the Cardinals plus some more to make the deal result in some Padres prospects also coming back. Of course, these prospects may also be used to send to the Yankees to get Gray, rather than give up someone like Kyle Lewis. I suspect Leake is not enough to get Francisco Mejia, but someone like Jacob Nix would be useful to either the Yanks or the Ms.
My guess is that Dipoto wants a young RH starter, which Gray still is at 29 with 5 years in the majors, to pair with Marco, and will take a chance on Myers stepping up as a performer on a young team (he's just a few weeks older than Mitch Haniger, but also has 5 years in the majors) with Ellsbury for a mentor at least for the first half of the season. By clearing Kyle, Leake, and Encarnacion from the payroll, even with Myers added, the future payroll room looks nice. Myers is entirely adequate at 1B, if not the hulking slugger normally envisioned, and can take the 5th OF / DH job when Ellsbury leaves and Evan White looks ready. He's expensive unless he takes the ever-anticipated step up, but his proven RH bat may be quite useful in a lineup that is currently very LH.
As to Jay Bruce, if some team shows even the slightest interest, I guess he is gone. Otherwise, he's another placeholder the Ms will try to flip to a contender at the deadline next year, when they call up Lewis or Filia to play LF. Swarzak is another potential deadline trade candidate, but his stock is pretty down now to return anything that useful. If the Ms can get Poche as a closer-to-be, Swarzak may be a good mentor there as well.
So, I expect Dipoto will continue the house-cleaning he has started, but things don't really look like a complete tanking tear-down. A rotation with Gray-Marco-Felix-Sheffield-LeBlanc is not notably weak if Felix can regain some moxie, and a lineup with Haniger, Myers, Ellsbury, Smith, Narvaez, and Gordon (with a good toe), is also not that weak. Add Crawford, Bruce and Gamel stepping back up, and it might be reasonably strong, if not as powerful as Cano and Cruz have made it the last few years. All but Bruce and Ellsbury still have time and room to grow into better hitters, though, so it's not like it's full of the whifftastic and the never-weres.
Then again, IFF the Ms can sign Kikuchi, that rotation starts looking REAL good! Sheffield can sharpen up in Tacoma while Felix either shows he's capable or becomes a very expensive mop-up reliever. By mid-year, with Dunn and/or Swanson coming along, there could be 5 studly-types in that rotation!
I am not going to be surprised if I hear Dipoto has signed Jose Iglesias as Crawford insurance, or Wilmer Flores to play 3B if Seager goes. Both are still pretty young (Iglesias is 29, Flores 27) and have been contributors in the past, if not offensive forces. And there's still a question if Freitas is going to be the B/U catcher, or they sign a placeholder like A.J. Ellis (player-coach?) or Devin Mesoraco. But the spots vacated still need some fill-in. For my Christmas present, Jerry could do another trade with Cleveland for a potential B/U catcher -- Sicnarf Loopstok*. Just hearing the Ms TV/radio crew pronouncing that would put some joy into the year!
I'm a bit discouraged by the "re-imagining", but if Dipoto continues on the same track I'm not ready to resign as an Ms fan. I personally suspect Segura showed during Cano's suspension that he isn't the best clubhouse citizen or teammate, so the trade with the Phillies was probably for the best once Cano was gone. And, if the ultimate return includes Gray, I'll personally consider the maneuver a success, in fact. With the prospects nearing MLB(tm) readiness like White, Bishop, Lewis, and Dunn, I'm actually pretty stoked for 2020, if not for 2019. We all should be a bit patient -- this actually might turn out nice!
Anyway, thoughts of a dry brain in a cold season.
Merry Christmas to all!! And may Doc receive the gift of health! I'm praying for him.
*From the Netherlands Antilles (Aruba), his father was Francis and in Dutch, loopstok is a walking stick or shepherd's crook. But he's also supposed to be a decent C prospect!