There are only three teams that have a smaller Largest Contract Ever than the Chicago White Sox, and those are the Oakland Athletics, whose biggest deal was for Eric Chavez in 2005 for six years and $66 million, the Pirates, who signed Jason Kendall for $60 million, and the Cleveland Indians, who signed Edwin Encarnacion (and then traded him) for $60 million. That makes it kind of odd that the White Sox are considered one of three finalists in the Manny Machado sweepstakes, but considering all of the context, it makes it perfectly reasonable.
What separates them from those previous three teams are obviously the market sizes; by Forbes they have a valuation $1.5 billion and a revenue of about $266 million, which puts them around the middle of the pick in value despite never having shelled out a single large deal in their recent history.
Owner Jerry Reinsdorf and company also secured a new TV deal with NBC Sports Chicago, and despite qualms over sharing this market share with the Blackhawks and Bulls, it could be a boon in terms of revenue that could both help them land Machado or Bryce Harper, and also have a multiplicative effect whereby it boosts both gate sales and TV ratings after the fact.
If you were to look at recent White Sox history, it may be already too late to spend, or maybe just the right time. Just a few years ago, before their tear-down that sent their core of Chris Sale, Jose Quintana, Adam Eaton, and David Robertson scattered across the league, they had the makings of a potentially dangerous team in the NL Central. They made some free agent splashes like for the aforementioned Robertson, Melky Cabrera, and Jeff Samardzija, but let’s be honest, we all knew that was never going to be enough to secure a division win or pennant.
Now, the tables have turned with a new generation of White Sox at the table. Jose Abreu is the only one remaining from the last core, still their largest contract ever, and he is now adjacent to a number of new and up-and-coming players. Eloy Jimenez, who came over in the lauded Quintana deal with their crosstown rivals, should bear some fruit in 2019: he hit .355/.399/.597 at Triple-A last season, and Steamer projects him as a 129 wRC+ hitter next season.
Yoan Moncada is the less-than-expected return from the Chris Sale trade, but you also can’t say he isn’t a cheap or justifiable return. He had a 97 wRC+, a 33.4% strikeout rate, and was worth exactly 2.0 fWAR last year, so if he could theoretically cut down on the strikeouts, and he is just 23 years-old, then he is a slightly-above-average hitter, and you need quite a few of those.
Their pipeline offers a ton of near-future solutions who could buttress a potential Machado or Harper signing. Luis Robert was signed for a massive (second only to Moncada’s) $26 million bonus, and as a 21 year-old possibly five-ish-tool center fielder ready by 2021, there could be hope that the free agent star’s prime could be timed along with his.
Nick Madrigal is the high-floor recent draftee at fourth overall last June, and he could be ready at the same time. The same could be said for the previous year’s Zack Collins, who hit at a 128 wRC+ clip in Double-A and despite some contact issues, average defense means he’s projected as an above-average starter.
Pitching could be trickier and more high risk, but in theory, if Reinsdorf is suddenly willing to spend for Harper, Machado, and whoever else, a pitcher down the line like Gerrit Cole, Sale, or Justin Verlander shouldn’t be out of the question.
Michael Kopech will miss all of 2019 due to Tommy John, and Dylan Cease may have command issues, but the bigger lesson from the last rebuild wasn’t so much as hitting on those guys (like they did with Sale and Quintana) but being willing to surround them with the talent they needed to succeed. If one succeeds, and they still have the likes of Carlos Rodon as well, they should have more than enough to contend if they are willing to spend.
A lot of people in recent analyses would probably argue they aren’t “ready” to spend because they aren’t “ready” contend. The fact is... a team is always ready. They did a half measure last time and it backfired, so the lesson is to never do it again? The fact is, if they are willing to sign Machado for the rumored eight years and $250 million or whatever it is, they are not jumping any gun.
There are deals that both make you good now and good later, and there are deals that do both. When you’re rebuilding, the latter is perfectly fine. It’s also an added confidence boost to anyone under the rebuild’s tutelage who sees this by saying that we are ready to win now, even if we aren’t as “ready” as analysts think we are.
Sure, even with Machado and Harper this isn’t much of a contention team in 2019. But with the Indians content in half-retooling and thinking they automatically have the division in the bag, combined with the rest of the division being a dumpster fire and the Twins as well in what looks like the last White Sox team’s quasi-contention, it makes perfect sense to step on the gas and hope the prospects catch up with the signed free agents. Because if it works, a tenure of Machado in Chicago could be quite successful and wise considering even the richest teams are deciding to pass for reasons unknown.