Zack Wheeler won't be joining the South Side starting staff, though not for lack of trying on behalf of the White Sox, who made a richer contract offer than the five-year deal Wheeler got from the Philadelphia Phillies.
But that effort alone won't plug the two holes in the White Sox rotation, and they'll need to go elsewhere to find the upgrades they need. Where?
Well, they can keep swimming in the same free-agent waters they hoped to pluck Wheeler out of, with a second tier of free-agent starters still out there populated by Madison Bumgarner, Hyun-Jin Ryu and Dallas Keuchel. You might ask why we're just skipping over Gerrit Cole and Stephen Strasburg, the perennial Cy Young types at the tippy top of the market, and that's a good question. But the White Sox haven't been linked anywhere near as strongly to either ace as they were to Wheeler, with MLB Network's Jon Heyman going as far as saying there's "no belief" the White Sox would pursue either guy. Though it's worth wondering whether Wheeler's decision to head to Philly makes the White Sox reconsider.
Anyway, we'll stick with those second-tier guys for now.
Bumgarner has long looked like exactly what this rotation needs, an accomplished pitcher who could serve as the Jon Lester for this Chicago rebuild. Bumgarner's a three-time World Series champ and might very well be the best pitcher in the history of the World Series, where he owns a career 0.25 ERA in five appearances. Even though he's already logged 11 big league seasons and has pitched in four different playoffs and has a combined 1,948.1 innings between the regular season and postseason, he's just 30 years old. The mileage on his left arm might make some wary, but after a couple of injury-shortened campaigns in 2017 and 2018, he made 34 starts for the San Francisco Giants last season. It's worth noting his 3.90 ERA in 2019 was the highest of his career, though it was also lower than Wheeler's 3.96 ERA.
In the wake of Wheeler picking the Phillies, the White Sox were already reported to be among the "heaviest suitors" for Bumgarner's services.
In the wake of Wheeler signing with Phillies and Hamels signing with Braves, Bumgarner market is clarifying. Per sources, White Sox and Twins among heaviest suitors there. Yankees involved to some degree.
— Andy Martino (@martinonyc) December 4, 2019
Ryu, meanwhile, had the lowest ERA among qualified starting pitchers in baseball last season, at 2.32, that dazzling number coming a season after he posted a 1.97 ERA in 15 starts. Durability has been Ryu's bugaboo. He missed the 2015 season, made just one start in 2016 and has averaged 22 starts in the three seasons since. But he's undoubtedly been excellent when he's been on the mound the last two seasons. Ryu is significantly older than Bumgarner; he'll turn 33 before Opening Day 2020.
Keuchel, who will turn 32 on New Year's Day, would also bring a winning history to the rotation. He's been through a rebuild and come out the other end a world champion with the Houston Astros. In 2015, he won the AL Cy Young Award. He hasn't been overwhelmingly consistent, following up the 2.48 ERA he posted during his Cy Young season with a 4.55 ERA in 2016. He had a 2.90 ERA the year the Astros won the World Series, but he's finished with 3.74 and 3.75 ERAs in the two seasons since. Keuchel was a victim of the draft-pick compensation triggered when he rejected the Astros' qualifying offer an offseason ago, remaining unsigned until June. The Atlanta Braves scooped him up then, and he did well down the stretch for the NL East champs, with a 3.75 ERA in 19 starts.
It should be noted the White Sox have other holes on the roster that need addressing this offseason, even if none might be more pressing than starting pitching. But should they decide to spend big on, for example, a right fielder (such as Nicholas Castellanos or Marcell Ozuna), perhaps the trade market is a more realistic possibility for finding that starting pitching.
It's also important to note that the White Sox are searching for two starting pitchers, meaning the second might be found in a lower tier than the one housing the three names discussed to this point. Past those three, the market thins significantly, with Michael Pineda and Tanner Roark potentially being the next most attractive options.
Options exist, yes. But they aren't exactly bountiful, especially if one of the two starters is desired to be a top-of-the-rotation type that can pair with Lucas Giolito to create a formidable 1-2 punch. If the White Sox are forced into shallower waters in their search for starting pitching this winter, that would put some more pressure on Michael Kopech, coming off Tommy John surgery, and Dylan Cease, coming off a 5.79 ERA in his first taste of the majors in 2019, to quickly blossom into top-of-the-rotation types.
There's a lot of offseason left, of course, and the White Sox are expected to continue their aggressive search for upgrades. As Wednesday showed, however, being aggressive and being willing to spend don't always equal success.