What factors into Sox signing Machado, Harper?

CHICAGO -- With one word in his Monday morning column on MLB.com from the General Managers Meetings in Carlsbad, Calif., Jon Paul Morosi sent White Sox fandom into a frenzy.
That word was "both," as in the White Sox perhaps could be in a position to add "both" infielder Manny Machado and outfielder Bryce Harper via free agency this offseason. Morosi followed that line with the caveat, "there's no guarantee they will land either," but White Sox fans already were gone.

Future lineups were being constructed with Machado and Harper. Parade routes were being discussed. Days off were being requested for late October, starting in 2020.
It's part of the Hot Stove beauty, when the seemingly impossible becomes believable. But let's take a deeper look into White Sox interest in these 26-year-old superstars.
Would the White Sox really sign both Harper and Machado?
General manager Rick Hahn bristles when people turn to what the White Sox haven't done in the past, quickly pointing out the ongoing rebuild and the addition of outfielder Luis Robert via the international market as changes against that perceived norm in the present. José Abreu's original $68 million deal (over six years) still stands as the richest one in franchise history, and even if the White Sox have offered more in other failed pursuits, it seems unlikely the organization will commit potentially $30 million per season over eight to 10 years to two players.
They certainly have the payroll flexibility to do so, with Cot's Contracts projecting them at $54,425,000 for 2019 and below $10 million in each of the three seasons to follow. Adding Machado and Harper would theoretically push the '19 payroll over $120 million but certainly wouldn't be the finishing move for the rebuild. It would give the White Sox even greater flexibility to package prospects to fill other voids with veterans.

Should the White Sox be in on both?
Absolutely. Adding either Machado or Harper makes perfect sense for the White Sox at this point of the rebuild. Take the Cubs' rebuild as an example: Jon Lester coming to the North Side prior to the 2015 season did not finish off the process, but it gave instant credibility to what the Cubs were doing, and the Cubs earned a Wild Card berth that year. The same feeling would manifest this offseason for the White Sox.
Does Machado and/or Harper want to come to the White Sox?
Here is the $350 million (or maybe even more) question. These top-level free agents enter the process knowing the team or teams they want to play for. Clubs outside that group can move their way into the mix via money and pushing the team's plusses. But in some cases, players rule out particular destinations.
Why would Machado and/or Harper want to join the White Sox?
These players could be sold on two major points, assuming the White Sox made an offer commensurate or even above other teams. Machado and/or Harper would have to truly believe in the young talent amassed by the White Sox translating into multiple future World Series contenders and understand they immediately become the face of that rebuild in one of the top three markets in the country. Chicago is an impressive city to add to the mix if you can overlook the unending road construction.
Does adding one of these two mean instant contention?
Michael Kopech's Tommy John surgery knocking him out for 2019 sets the White Sox back a bit. But in the American League Central, with all but the Tribe rebuilding, it's possible for the right moves to push the White Sox from 100 losses in '18 to competitive.
Who would you pursue?
I'd go after Harper first. Think of an outfield with Eloy Jiménez, Robert and Harper left to right, and an infield of Yoán Moncada, Tim Anderson, Nick Madrigal and let's say Abreu third to first, with Zack Collins at catcher. Not a bad group to hit the diamond.

Do the White Sox have other needs this offseason?
Hahn plays things close to the vest, but he has stated on a couple of occasions the need for pitching, both starting and relief. Again, it's important to stress this offseason doesn't signal the end of the rebuild -- it's closer to the beginning. But bringing on Machado or Harper could speed things up exponentially.