Who did it better
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This is obviously a hard question to answer and one that is very subjective. We won’t really know the answer until a couple of years from now.
It really is quite comparable when you look at the two teams and where they are right now.
You could say that San Diego has done better in the free agency market because they’ve been able to sign the superstar player in Machado. I don’t care what Jon Heyman or anyone else says, that Machado signing was a win for San Diego and will be for years to come.
But, when talking about the future, the Padres have gotten themselves into some bad deals that are going to hurt them going forward with Hosmer and Wil Myers.
While the White Sox haven’t made the huge splash in free agency for a superstar player, they also haven’t hampered their future payrolls by getting stuck in long contracts.
San Diego has done much better in the draft and international market than the White Sox.
And even though the Padres got a couple of potential superstars in Paddack and Tatis Jr. through trades, I’d probably still give the edge to the White Sox for the depth of quality talent they got back in their trades.
Padres potential 2020 lineup: Tatis Jr., Pham, Machado, Hosmer, Myers, Girsham, Profar, Mejia.
White Sox potential 2020 lineup: Moncada, Robert, Abreu, Encarnacion. Grandal, Jimenez, Anderson, Mazara.
I like the White Sox lineup better as it has much more depth even though the top of the Padres lineup is probably better.
Padres potential 2020 rotation: Paddack, Richards, Lamet, Davies, Quantrill/Gore
White Sox potential 2020 rotation: Giolito, Keuchel, Gio Gonzalez, Cease, Kopech/Lopez
I really like the White Sox rotation too, but I’ll give the nod to the Padres.
Chicago plays in a pretty weak division, so it wouldn’t surprise me if they competed for the AL Central and an AL Wild Card spot in 2020.
It would be quite the shock if San Diego even sniffed the NL West division title over the Dodgers if another big move isn’t made, but they should at least be in contention for an NL Wild Card spot.
The two rebuilds are very similar and I can’t wait to see the turnaround for both clubs. If Gore and Patino come up and be what we expect, then I’d say the Padres are better setup for the future.
But it’s really that close that it could hinge on whether or not those two become top of the rotation pitchers.
Rebuilds are not fun to go through, but once it’s time to turn things around it’s a lot of fun to go back and look at how it happened. For the Padres and the White Sox, I really hope 2020 is the season when they start to contend. And how fun it would be if these two teams meet in a World Series soon?