Riffing off a post in the general offseason thread...
Short term, the joke is likely to be on other teams after the Yankees scoop up Harper, Machado and maybe both at rates that will appear to be bargains compared to what the expectations were a few years ago.
NY is around $213M currently for 2019. I don't personally think this would be the smartest way to proceed, but...
Trade Andujar along with Ellsbury (21/21/5 remaining on his contract) to SD for Manny Margot, SD is evidently really high on Andujar to fill their 3B spot next to Tatis and Urias at SS/2B, and they have very few financial commitments so could swallow the Ellsbury money if they wanted to (and in fact NY/SD did a smaller version of this last winter with one year of Headley's money bundled with the unharnessable talent of Bryan Mitchell for basically nothing in return). If that's not fair as is, it could be evened out with secondary players to make it work. Andujar has much more value to SD than NY (they can let him try to get better at 3B for a year or two, and if that's still not tolerable, I think he could be OK in LF), I actually think that would be smart for SD to jump on if offered as Andujar looks to have a special bat and they seem to have soured on Margot, who would be a great organizational fit for NY in AAA between Hicks (FA after 2019) and the still super young and a few years away Florial.
Sign Machado and Harper to matching 8/208 ($26M per) deals with a player optout after 2 or 3 years. Obviously I have no idea if that would be enough but given the marketplace and that we know both players would prefer to play for the Yankees if possible, it's an idea.
That would put NY around $244M, still somehow under the top tax level, and with the following team:
Torres 2B
Judge RF
Harper DH
Stanton LF
Machado 3B
Hicks CF
Sanchez C
Voit 1B
Tulo SS (Didi on the DL)
Bench: LeMahieu, Gardner, Romine.
Clint Frazier, Margot (2 options left), Bird, Wade all in AAA.
Yowza.