Joe Throwback: Kenny Williams

Funny thing about writing: Sometimes you write something and don’t think much about it and it ends up going viral and becoming super-popular. And sometimes you write something and you think, “Hey, this one’s pretty good,” and then nobody reacts to it. I remember being kind of proud of this story about White Sox president Kenny Williams back in 2010. But it didn’t seem to resonate with readers. That’s OK. I still like it.

Kenny Williams does not like the way this interview is going, which is a bad sign because the interview has not started yet. He does not like it because he knows there will be questions. Questions, to a man like Kenny Williams, demand honesty; he has never quite forgiven the people in baseball who lied to him. Honesty, to a man like Kenny Williams, demands introspection. And introspection, to a man like Kenny Williams, demands thinking about some things that he would rather not think about.

Things like: “What am I doing in this game?”

And also: “No, really, what the hell am I doing in this game?”

No, Kenny Williams does not like the way this interview is going, though not a single question has been asked yet. Of course, he does not retreat. He never retreats. He sits still on the bench at U.S. Cellular Field, and he stares out at the field, where the Minnesota Twins take the last swings of batting practice, and he says this: “I don’t do interviews like this. I don’t talk about myself. That’s not what it’s about. That’s not what I’m about.”

“Would you rather not do it?” he is asked, the first question.

“Well,” he says in a resigned way, “you’re here.”

He stares back out at the field. An autograph seeker has spotted him in the dugout, and she shouts out, “Kenny! Kenny Williams!” He does not seem to hear her. The cracks of the bat lock his attention. The Chicago humidity makes his shirt stick to his back. He says, “I was not built for baseball. One hundred sixty-two games? Spring training? The postseason? Come on. All those games? I’m not a baseball guy. I’m not built for this game.”

Kenny Williams is thinking about something.

“You know I love this city,” he says. “I love my job. Understand that. Get that part right. I love what I do, and I love where I am. But if the Oakland Raiders called tomorrow and asked me to run the team, I would go. I would do it.”

He wants me to write this down. I write it down. He is joking. He is not joking.

“Don’t misunderstand,” he says. “Get it down right. Get it down that I love what I do. Don’t get it wrong, now. I absolutely love what I do.”

“But you would leave to run the Raiders?” I ask. It’s the second question of the interview. Kenny Williams keeps staring out at the field and, for the first time, with a hint of a smile on his face.

“I’d have to go,” he says. “I’d have to tell people, ‘Sorry, I’ve been called home. The Silver and Black has called me home.’”

White Sox owner Jerry Reinsdorf talks with Williams before the club honored Harold Baines in 2019. (Nuccio DiNuzzo/Getty Images)

Of course, Kenny Williams claimed Manny Ramirez. It had to be that way. The White Sox are in second place, which means they are not in first place, which means that Kenny Williams had to do something. Truth is, when the White Sox ARE in first place, he still has to do something. There’s a story about Williams, a story that you will hear over and over around Chicago as people fitfully try to explain the unexplainable: What burns inside one of baseball’s most confusing men.

“Oh, you want to know about Kenny,” they will begin, and they will tell you this story. The White Sox had won the 2005 World Series — the first baseball championship in the city of Chicago since 1917. And a lot of people around the game whispered that Kenny Williams got lucky. That’s something else about Kenny Williams. People around the game tend to whisper about him.

Whatever. Every move he made that year, even moves that were savaged when they were made, more or less worked. The White Sox let go of four-time All-Star Magglio Ordonez and signed Jermaine Dye, who was 31 and seemed older and had been mostly mediocre in Oakland.

Williams traded hard-hitting Carlos Lee mostly for speedy and decidedly not hard-hitting Scott Podsednik.

Williams picked up underachieving reliever Bobby Jenks off waivers, signed 32-year-old Dustin Hermanson coming off a blah season, and signed a 39-year-old El Duque for quite a lot of money.

In January, Williams signed A.J. Pierzynski, who was coming off a dreadful year in San Francisco, where he had solidified his reputation as one of the more disliked players in the game.

By this point, Williams had already traded prospects for Freddy Garcia and traded two-time All-Star Esteban Loaiza for the disappointing Jose Contreras.

None of these moves, not one of them, was considered especially brilliant when he made them. But every last one of them worked, as did his hiring of the flamboyant, erratic and irrepressible Ozzie Guillen as manager. The White Sox won 99 games and then rolled through the playoffs and the World Series in record style, winning 11 of 12 in October.

OK, so there was Kenny Williams at the end of one of the more rewarding seasons ever for a general manager. After the final game, the White Sox players and coaches and everyone loaded on the bus, and it reeked of champagne and sweat and joy, and the celebration raged on, and it was then, at precisely the happiest and most content professional moment of Kenny Williams’ life, that he slid next to Ozzie Guillen and said: “OK, here’s what I’m thinking about next year’s team.”

He was joking. He was not joking.

“I really do not handle success well,” he says. But, he admits, he handles failure even worse. And right now the team’s in second place, and that’s the worst place. Second feeds on his strongest and fiercest impulses. In first place, sure, he’s uneasy. In third or fourth place or fifth place, yes, he’s furious.

But in second place, he is incomplete. Second place could be first place. Second place should be first place. He has to do something!

While so many other general managers around baseball like to talk, like to weigh, like to contemplate and ruminate and deliberate, Kenny Williams ACTS. The football player inside him rages. The son of strivers has something to prove. When the Dodgers put Manny Ramirez on waivers — Manny Being Manny, the fiercest, strangest, most brilliant conundrum in baseball over the last decade — everybody KNEW Kenny Williams would sign him. Of course, he would.

The White Sox were in second place.

“Do you think Ramirez will be the difference?” he was asked.

“I can’t see the future,” he grumbled. It was a dumb question. The right question to ask was: COULD Manny Ramirez be the difference? That’s the point, the only point. And of course, he COULD be the difference. This is another thing people miss about Kenny Williams. It’s not about being right or wrong with him. It’s about doing something.

It’s two weeks later now, and Manny Ramirez has not been the difference-maker. The White Sox are still in second place — by eight games now. It’s mid-September. The war is almost over. Time runs out. And Kenny Williams is still incomplete.

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Sometimes when Kenny Williams finds himself crawling into himself, he goes to the car. He drives. That calms him a little bit. He can’t say why. It’s not like Chicago traffic — all those cars stopping and starting and coughing exhaust fumes all around him — should be relaxing. But somehow, it is.

He doesn’t know why. There’s something about the windows being rolled up, maybe. There’s something about the stifling air. There’s something about the car movement. Who knows? He just knows that when he’s driving, when he listens to games on the car radio, Ed Farmer and Darrin Jackson bringing him the news from across town, yes, he can almost tolerate the games. Failure doesn’t feel so close.

Failure got him into this game, he will tell you. The White Sox had drafted him in the third round in 1982, and Jerry Reinsdorf himself walked into his home to recruit him to play for Chicago (“Only time I’ve ever done that,” Reinsdorf has said.)

Kenny Williams’ baseball talent was unquestioned. But, he always felt more like a football player. He played football at Stanford for a year; he was on the same team as John Elway.* Even as a freshman, he was Stanford’s top returner. He was fearless on a football field. The sport matched his personality. Kenny never felt more like himself than when he was in his football uniform.

*At the end of that season, Stanford famously lost to Cal on The Play — you’ll remember it, all those laterals, Stanford’s band ran on the field, etc. Williams played in that game, but he was not on the field for that play. He believes, to this day, that if he had been on the field, he somehow could have altered college football history.

So why did he choose baseball? The answer will blow your mind: He chose baseball because of failure.

“I hit like .230 my first full year in the minors,” he says. “That’s why I chose baseball.”

He is joking. He is not joking.

“I had never failed before,” he says. “At anything. I had to play baseball. I had to conquer it or something.”

He shrugs. Williams admits he is drawn to failure as much as he is repelled by it. He seeks out failure so he can vanquish it. It’s just what’s inside him.

Maybe that comes from family. His father, Jerry, sued for the right as a Black man to be on the San Francisco Fire Department. His mother, Ethel, climbed the corporate ladder as a business executive at a time when there weren’t many women executives, and there certainly weren’t many Black women executives.

Kenny himself is the first African-American to run a sports franchise in Chicago, and he’s only the third Black general manager in the history of Major League Baseball. The Williamses are a family of achievers. Kenny Williams isn’t the only successful person out there who believes that he will never accomplish as much as his parents. But he’s the only one running the Chicago White Sox right now.

“I just wasn’t cut out for baseball,” he says again. And he’s right, he wasn’t, not as a big-league player, anyway. He did make it to the big leagues, which would have been a grand achievement for another man. He had some power, had some speed, and he showed some promising signs as a rookie in 1987, when he hit .281, hit 11 homers, stole 21 bases, played a sound centerfield.

But Williams has always had trouble with the bad days. How do you conquer the bad days? How do you turn that last strikeout into a triumphant homer? To hit, to field, to perform over a long season, you need a quiet mind. Kenny Williams’ mind is anything but quiet. The White Sox moved him to third base his second year, and he hit .159 in half a season. He hit .189 for the rest of his big-league career.

He was cut out for football.

“I just don’t have the ability to control my aggression,” he says. “I’ve gotten better. Believe me, I’ve gotten better. But baseball is really the polar opposite of football when it comes to that. Football is an aggressive act. Baseball is not. And that was my downfall.”

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Kenny Williams wouldn’t want to hear this — but his story is eerily similar to that of Billy Beane. He wouldn’t want to hear this because he has been labeled as the anti-Beane. In Moneyball, he more or less represented the clueless baseball people — “He doesn’t need any motivation … but I think the Moneyball stuff really bugged him,” one of Williams’ close friends says — and Beane has made a handful of high-profile trades with Williams that have not necessarily worked out for Kenny (Baseball Prospectus once ran a story with the headline: “Kenny Williams, A’s Fan”).

Also, it has long been trendy to celebrate Billy Beane as a new kind of GM (relying on stats and various other objective measures) and saddle Kenny Williams with the old-school tag (relying on gut and such).

But… eerily similar stories.

— Both were California high school kids, brilliant in multiple sports, Stanford types, (Beane also had interest in going to Stanford to play football and baseball).

— Both carried cute first names and strikeout swings and competitive furies that made pro baseball a tough game to play.

— Billy Beane hit .219 for his disappointing big-league career. Kenny Williams hit .218.

— They both retired — or were retired — at 27.

— When his baseball playing days ended, Billy Beane approached Oakland GM Sandy Alderson and asked if he could be an advance scout. Kenny Williams approached Chicago White Sox owner Jerry Reinsdorf and asked if he could try to find hidden talent in America’s inner city. Alderson and Reinsdorf mentored their former players.

— Beane became Oakland’s GM when he was 36. Williams became Chicago’s GM when he was 36.

— Beane’s teams, facing small payrolls and being viewed as second-best in a huge market, have won 53.8 percent of their games and made the playoffs five times.

— Williams’ teams, facing an identity issue and a divided Chicago and a long history of mediocrity with a couple of near-misses, have won 52.4 percent of their games and a World Series.

So why are they viewed so differently?

“I think Kenny and Billy are actually very much alike,” says another person close to Williams (nobody wants to be named when talking about Kenny Williams). “I don’t think that Kenny would agree with that, and Billy might not either, I really don’t know. They do look at the game somewhat differently, maybe. Billy might be more stat-oriented and Kenny more scout-oriented. But as far as their personalities, their commitment to winning, I think they’re a lot alike.”

One thing they share is their laser focus on winning. When they call about a trade, they’re not calling to chat. Williams, in particular, is well-known around baseball for his bluntness. “With Kenny, there’s no B.S.,” one GM says. “I like that. He’s not calling to feel you out. He’s not calling to play games. When Kenny Williams calls, you know that he means business. He wants to get something done.”

That doesn’t mean that everyone in baseball is a fan of Kenny Williams. As mentioned, there are always so many whispers going.

“I know a lot of people in the game who think he’s kind of a mess,” one baseball executive says. When pressed to explain the reasons, he will only say: “I don’t know. I respect Kenny, I think everyone has that respect for him because he’s aggressive and is not afraid to make a mistake. But the moves he makes don’t often seem to make sense. Look at the Rios thing. That’s a perfect Kenny Williams move. It makes absolutely no sense until …”

Until it does. That’s the Kenny Williams slogan. Williams took a huge beating around the league last year when he picked up Alex Rios on waivers from Toronto. By picking up Rios — who was in the middle of a terrible season — the White Sox assumed a $60 million tab that will stretch out until 2014. Williams (backed by Reinsdorf, of course) was willing to bet big on Rios returning to All-Star form at a time when, you can be absolutely sure, nobody else in baseball would have made that bet. Nobody. There were rumors of a big celebration in Toronto after they were able to clear Rios’ salary. It makes no sense until…

Until it does. Until this year, when Rios, 29, is playing just about at the All-Star level he was playing at when he got the big-money deal in the first place. And suddenly, the White Sox are set in centerfield for years.

“You know what?” Williams says. “It’s our fault — it’s my fault in particular — if we don’t get a lot of credit for what we’re doing here. There are some people in this game who go around saying, ‘We’re trying to do this,’ and ‘We’re trying to do that.’ There are people who remind everyone of the good moves they made. And they get a lot of press for that. We just don’t do that. We fly low and try to get the job done. So, no, people don’t talk as much about what the Chicago White Sox are doing.”

“Does that matter?” I ask. “Do you care what people think?”

Kenny Williams pauses. He knows what he should say. But questions to a man like Kenny Williams demand honesty.

“Yeah, I care,” he says. “I wish I didn’t.”

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The day Kenny Williams took over as GM of the Chicago White Sox, he had scheduled his first 365 days. It wasn’t a firm schedule, understand. He always gave himself the freedom to back away from it, go do something else. “I’m not rigid about it,” he says. “I’m really not.”

But it doesn’t change the point: Before he ever started as GM, he scheduled every single day for a whole year. He still has a detailed schedule that stretches throughout the entire year, day by day.

“But,” he says, “sometimes I’ll go a couple of weeks without even looking at it.”

He has an organized mind, that’s all. On his Wikipedia page, it once said that he claims to have eaten a peanut butter and jelly sandwich every day for nine years, a statement he says is absolutely ridiculous (“I have no idea where that came from… I probably haven’t had a peanut butter and jelly sandwich in like 13 years,” he insists).

But Williams’ obsession with order has reached urban myth proportions, Wikipedia proportions, in large part because, like all urban myths, it COULD be true. Kenny Williams is regimented. He is organized. He may not eat peanut butter and jelly every day, but it’s not hard to imagine. He craves order.

His appreciation for order tends to counter his own acceptance of chaos. Everyone knows that the atmosphere with the White Sox is lively. Every day, it seems, there are clashes. Every day, it seems, there are surprises.

“There is not a single guy in that clubhouse,” Kenny Williams says, “not a single guy that I haven’t had an argument with. And most of them I’ve had several…. We have an open environment here. Everyone is going to know exactly what I want from them, and what I expect from them. There are no secrets. And if that leads to arguments, so be it.”

Williams believes that crackling tension is part of what makes the White Sox successful — not unlike his beloved Raiders. He does not want people around him to hold back. He does not want people around him who think the way he thinks.

“The second you think you’ve figured out this game,” he says, “that’s when it’s going to come up and kick your ass.”

Take his manager, Ozzie Guillen. It’s well-known that they have their differences. They are different in every possible way. So those two clash and they hug, and they embarrass each other, and they fight constantly. Ozzie says some crazy things, and Williams shrugs.

“Look, not a day goes by that I don’t ask myself if it’s worth it,” Williams says. “But I think it is worth it. I think the creative energy Ozzie brings fits what we’re trying to do.

“Sometimes I have to remind myself this is what I want. I have to remind myself going into the year that just about every day somebody’s going to do something that pisses me off. Somebody’s going to challenge me. This is what I want. This is really what I want. But, yeah, I do have to remind myself.”

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The White Sox are not going to catch the Twins this year. The math makes that clear. The White Sox got a lot better this year – with a late rush they still could win 90 games after finishing below .500 in 2009 — but Kenny Williams will take little solace in that.

“You win or you don’t,” he says.

He will probably have a few more painful days left this season, and then … well … he doesn’t know now. Every year takes a lot out of him. This year has taken out even more. He has spoken publicly about the possibility of leaving.

“I will not deny that I’m growing weary of the soap opera,” he told MLB.com back in June, back when he and Ozzie Guillen were clashing even harder than normal.

“This has been some year,” he told reporters in August after Ozzie’s son Oney took some shots at Williams on Twitter.

There has been sharp criticism of Williams and Guillen in Chicago, mainly for not bringing back Jim Thome, who has been a difference-maker for the Minnesota Twins. Manny Ramirez, Williams’ desperate last shot, does not have an extra-base hit or an RBI since coming to Chicago.

Anyway, the season is not quite over, and the EKG has not quite flatlined, and there’s another game tomorrow.

Kenny Williams has a letter framed on his wall that he likes to look at now and again. It’s a letter he received from Oakland Raiders owner Al Davis a few days after the White Sox won the World Series. He still remembers the thrill he felt getting the letter, with its embossed silver and black lettering, The letter congratulated Williams for a job well done, and for doing things the Raider way. It’s one of the prize possessions of his life.

“It would make more sense for me, the way I am, to run the Raiders,” he says. He is joking. He is not joking. Doctors have told him he has to calm down, has to stop letting the games of a long baseball season detonate inside him, and he says that he is trying. “I’m getting better, I really am,” he says, and then he admits that he can’t stop being himself. The only escape is to go out to the car and drive around and listen to a few innings on the radio. But it’s a temporary escape.

“Sometimes, I think about why I’m like this,” he says. “Why does it mean so much to me? I know that these are just games. I know. I look at my parents and what they had to go through, what they had to accomplish. I know that what I do … it matters, I’m not saying it doesn’t matter … but it’s sports … these are games … and I just … why does it matter so much to me?”

He stops and looks me straight in the eye.

“See,” he says, “this is why I didn’t want to do this interview.”