I write a lot about Jon Lester.
He’s a great pitcher who gives a mighty interesting quote, but that’s not why I, your friendly neighborhood White Sox scribe, write so much about Jon Lester. It’s because of what Jon Lester did for the Cubs and what the White Sox need somebody to do for them.
Well, the White Sox might have just found their Jon Lester in Dallas Keuchel.
Keuchel is reportedly joining the South Side starting rotation, a huge, splashy addition that White Sox fans were waiting for Rick Hahn and his front office to deliver this offseason. Yasmani Grandal was one, and now Keuchel is one, too.
But simply being a really good player who gets a rich, multi-year contract does not make you a Jon Lester.
Lester bought into what Theo Epstein and the Cubs were building after the 2014 season, a campaign that saw 89 losses on the North Side. Kris Bryant, Addison Russell and Kyle Schwarber hadn’t even been called up from the minors yet. But Lester, thanks to a longstanding relationship with Epstein and the brass he brought over from Boston, bought in. He got one of the biggest paydays in Chicago sports history to do it, but he bought in. He, along with a new manager in Joe Maddon, turned the Cubs from a work in progress into a contender. In his first year with the team, the Cubs went to the NLCS. In his second, they won the World Series.
Basically, Lester made the Cubs legit. Will Keuchel play a similar role for the White Sox?
Time will tell, of course. Part of what made Lester “Lester” on the North Side is that he pitched tremendously, at an All-Star, Cy Young level. He gave the Cubs an ace who could dominate in the postseason. He brought two World Series rings from his time with the Red Sox and he brought an attitude and he brought winning culture to a team that had never had it.
Keuchel checks plenty of those boxes, a Cy Young winner, a World Series champ and unlike Lester, someone who’s been through a rebuild and come out the other end with a ring on his finger. He’s got plenty of winning experience from his days with the Houston Astros, and he’s fresh off a brief stint with a young Atlanta Braves team that had championship aspirations in 2019. He’s also a phenomenal defensive player, with four Gold Gloves under his belt. He’s getting a lot of Mark Buehrle comps, and being the next Mark Buehrle would be welcomed on the South Side just as much as being the White Sox version of Jon Lester would be.
But Keuchel could do what Lester did: He could make the White Sox legit.
Folks have been looking for the White Sox to plant their flag, to say, “We’re here to win and win now.” And they’ve done all they can do in that regard, developing a talented young core and signing two All Stars in Grandal and Keuchel. The players are the only ones who can truly declare that the White Sox have arrived. That’s up to Keuchel and Grandal and Jose Abreu and Eloy Jimenez and Yoan Moncada and Lucas Giolito and Tim Anderson and Michael Kopech and Luis Robert.
Keuchel, by virtue of his veteran status, will likely be shouldered with leadership expectations. Can he take what he’s accomplished in his career and turn it into a Lester-esque second act?
It’s important to note that Keuchel is not the same pitcher he was when he won the Cy Young half a decade ago, and so perhaps we shouldn’t expect him to carry a load at the front of the White Sox rotation like Lester did for the Cubs. Lucas Giolito will still have a huge part to play in guiding this starting staff on and off the field, with Hahn mentioning Giolito’s burgeoning leadership qualities earlier this offseason.
But Keuchel has bought in, coincidentally also after an 89-loss season. Surely a potential $74 million payday over the course of four seasons had a lot to do with it. But he’s here now, a part of the long-term plans on the South Side. His biggest influence might not come in luring other free agents to the White Sox but in producing on the field, having a significant impact in the clubhouse and stepping up when the moment calls for it, be that in a pennant race or in the postseason itself.
Imagine the White Sox hitting the postseason stage for the first time in more than a decade with a bunch of youngsters getting their first spin in the glare of October lights. And who’s taking the ball for the South Siders? The guy who’s been there and done that.
Keuchel wasn’t the White Sox first choice for a splashy offseason pitching acquisition. They tried to sign Zack Wheeler to a five-year deal, offering him more money than he took to pitch for the Philadelphia Phillies. (It’s quite possible they could have wanted both, of course, but at the very least Wheeler’s decision came earlier in the offseason calendar.)
But Keuchel could end up being the right choice, certainly someone with a better resume who brings some different attributes to the South Side. Maybe Wheeler could have filled the Jon Lester role in his own way, but he isn’t that type of accomplished veteran. Keuchel is.
Again, time will tell whether Keuchel can have a similarly massive impact on a Chicago rebuild. But in this earliest stage of his South Side tenure — the deal hasn’t even been made official, as of this writing — he’s already made these White Sox a threat to make some noise as early as 2020.
He’s already made them a lot more legit.