Jerry Reinsdorf has been the owner of the Chicago White Sox since 1981, when he purchased the franchise for a whopping $19 million. The valuation of the franchise currently stands per Forbes is $1.9 billion. To date, the White Sox have yet to deal out a contract bigger than Yasmani Grandal’s, which tallies to $73 million. Quite a few teams, including the Padres, Orioles, Marlins, Rays, Reds, and Rockies have all dealt out contracts that are bigger; most had maximum deals that were triple or quadruple that of Grandal.
This is all to say... Reinsdorf has tallied up a mighty amount of coin over the years that has gone unspent. White Sox General Manager Rick Hahn was even quoted by saying that “[A]t the same time [as being on-board with rebuilding], there’s more than one conversation every week when he reminds us how old he is and wondering how much longer he has to wait to get to the promised land. He’s ready to get to the winning stage.”
It wasn’t long ago, remember, when Chicago should have been at that winning stage. When the team had a fine-enough core of Chris Sale, Jose Quintana, Jose Abreu, and Adam Eaton, their version of “all-in” was signing David Robertson, Melky Cabrera, and Jeff Samardzija in the 2014-15 offseason. In 2015 the trio put up 2.3 rWAR, and the team won a total of 76 games. You know the rest of the story; Sale, Quintana, and Eaton went off to greener pastures, two of them winning a Championship, and the team rebuilt anew.
Now after seven straight years of finishing at least 16.5 games back of first place, there’s a glimmer of hope. Grandal is one of them, as he adds about five wins in the immediate. The acquisition of Nomar Mazara, acquired for Steele Walker (lol, I’ll type this name up as much as I can), gives them an edge over replacement level in right field. There’s also a fine, young core coming into form that makes this signing, but not this signing alone, necessary in making this a winning club.
Based on recent ZiPS projections, it seems that will still be wholly insufficient. Someone did some good back-of-the-napkin math in the comments that tallies this to something like 30 WAR, which is imprecise in that we don’t really know playing time breakdown. But if that’s even close to the truth, this is a team slightly below .500. With Cleveland shopping Francisco Lindor and having already shipped off Corey Kluber, and teams like the Royals and Tigers in a full rebuild, essentially only a hobbled Cleveland team and the Twins stand in their way of the division.
As of now, there are four major improvements available to the White Sox on the free agent market: Josh Donaldson, Marcell Ozuna, Hyun-Jin Ryu, and Dallas Keuchel would all be improvements in right field (by a factor of ~3 wins) and in the rotation (by a factor of ~2.5 wins), while Donaldson’s would require some shuffling so it would be a little more unclear, but close to ~4 wins. Regardless, this bumps the team from ~78 wins to ~83, which we could say by a standard bell curve offers them about a 1⁄3 shot of winning more than 90 games.
That’s not even including the players for which improvement will continue. Yoan Moncada is improving. Lucas Giolito has advanced by light years. The likes of Luis Robert, Nick Madrigal, and Eloy Jimenez could all be 3-5 win players in their own rights.
Which is why you really can’t wait. With the AL Central on the downward trend, waiting would only allow other teams to advance in their rebuilds, putting Chicago in the position where maybe 85 or 90 or even 95 wins (look at the AL East) isn’t enough to nab a spot, thus pushing the standards for whom they need to acquire. If anything, they already made a mistake in not making a bigger push for the premier free agents, like Manny Machado, who would still be solid contributors by the time their core is fully rounded into form.
The worst case scenario, as we saw in 2015, is a half-measure. Given the options available it’s pretty unforgivable if the team fails to sign no more than a single player given the division and their historical non-spending; now is the time to strike, or it’s 2016 all over again.