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Come Fan with UsFriday, July 10, 2026

Kenny Williams Guiding His Son Through Dark Times

Chicago White Sox GM Kenny Williams has a history of curious moves as a general manager, but he also has the most clearly defined role of his life.

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Kenny Williams might be the president of the I Can’t Believe He Won a World Series Club. I’d like to think there are rabid Brian Sabean partisans who take pleasure in filibustering the election process, but Williams is definitely a bigwig. He controls the personnel moves for a team in one of the biggest markets in the game, and he often makes controversial moves. That’s a good way to build up a thick skin.

So when his son, Kyle Williams, made a pair of crucial fumbles in the NFC Championship Game almost two weeks ago, Kenny was probably as prepared as any father could be to offer his son support. From an interview with the New York Times:

After everything Williams has been through personally and professionally during his son’s formative years, he said Kyle is well equipped to handle life in the public eye — both the good and the bad. “He’s seen my mail,” Williams said. “I have firsthand knowledge of what it’s like. He grew up in a house where it was discussed and talked about what to expect.”

I really don't care about the White Sox, but I'm pretty sure that even I sent Kenny Williams a nasty letter after he picked up Alex Rios. The Blue Jays essentially put up a Craigslist ad that read, "$50,000 - 36 Boxes of AOL Free Trial CDs - Buyer Hauls," and where the right-thinking world knew to sprinkle holy water on their computer and slowly back away, Williams thought, "Wow! Thirty-six boxes! What can't you do with all those? I wonder if I can talk them down to $75,000!" So, no, he's not a stranger to criticism.

Kyle Williams had the misfortune of making his blunders in an age where there isn’t a cooling-off period between reaction and action. It used to be that the cranks would have to get out a piece of stationery, write the danged letter, affix the postage, and drop it in a mailbox. At any time during the process, the offended soul could think, “Wait, this is the kind of thing that an unhinged, awful person would do. I should probably reconsider.” With the immediacy of Twitter, Kyle (and his family) received threats within the hour.

I’ve watched every game of Kyle Williams’ professional career. He moved from a sixth-round pick (in football terms, a non-prospect) to the regular offensive rotation quickly, partly because of injuries, and partly because he had been impressive. He dropped to the sixth round because of his size, but it was clear that he was always one of the fastest players on a field filled with players paid millions in part because of their speed.

And it always tickled my funny bone whenever they'd bring up the little tidbit that his dad was the GM for the White Sox. I'd usually make a Juan Pierre joke. My three-year-old daughter wouldn't get it, but you have to start them early, like you might with a foreign language.

And when Kyle Williams made those four errors (two of which were just close calls, but still egregious flubs), my heart sank as a 49ers fan first. But after the game, my heart sank for Kyle Williams, who would have to live out the rest of his career with this game being a header on his Wikipedia page. Until further notice, this is what defines him. Just as we know Freds Merkle and Snodgrass more than a century later because of how they messed up, so too will Kyle Williams’s name be synonymous with something unfortunate for the next few decades. Bill Buckner had over 2,700 hits, but what did you think of just now?

With that in mind, it’s hard to consider Kyle Williams as a lucky man. But he’s pretty lucky that he grew up with a dad who knew one of the universe’s greatest truths: There are some idiots who take sports too damned seriously. Kenny Williams began the 1988 season as the White Sox’ starting third baseman, where he made 14 errors in 32 games. He finished the year with a .159/.221/.305 line. You can be sure that the majority of the correspondence he received didn’t include a lot of keep-your-head-ups.

During that 1988 season, though, Kyle Williams was born. During the toughest time of Kenny Williams’s career, he got the biggest jolt of perspective that a human being can get. His priorities surely shifted. Whatever had been important was knocked a peg down.

Now, with his son having a low point in his career at the exact same age, Kenny Williams seems uniquely qualified to help guide his son through a rough patch that few athletes will ever experience. He can point to his World Series ring as evidence that things can get better, that hard work doesn't always go unrewarded. He can point to redemption stories like Dustin Hermanson, who went from first-round injury-flameout to World Series-winning closer just as his career was about to expire. He can point to how during the darkest moment of his professional career, he had a son who never stopped putting things into perspective.

And he can mention that there are some people who take sports too damned seriously, and that those people are better ignored. It wouldn’t mean as much coming from just about any other dad.

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