Asking Kenny Williams if he's pleased is a little like asking your average neurotic comedian the same question.
Pleased? Are you kidding? The next step would be happy. The man still can't watch a Chicago White Sox baseball game in its entirety because it's too painful (think Brad Pitt working out in "Moneyball"). So watching his team defy most sensible predictions and remain in the thick of the playoff hunt in mid-August has to be pure torture. And even if it wasn't, he wouldn't tell you.
The White Sox general manager does reveal that he has been significantly inspired by Colin Powell's latest book, a memoir titled "It Worked for Me: In Life and Leadership," but is instantly sorry.
"I probably shouldn't have shared that," Williams says with a forced laugh.
In the first chapter, Powell expands upon his documented "13 Rules of Leadership," which include:
It ain't as bad as you think.
It will look better in the morning.
Don't let adverse facts stand in the way of a good decision.
And no doubt a Williams favorite: Don't take the counsel of your fears or naysayers.
Seemingly convinced for at least part of his 12-year tenure as Sox GM that the pockets of critics and handful of outright racists made up the majority, Williams has seemingly conquered that.
"It's something you have to develop very early on in your tenure and that's a tough, thick skin," he said. "You've got to understand that all you're able to do is exhaust yourself in trying to make the club and organization as good as it can be and if certain things don't break your way, it is professional sports and everybody is trying to do the same thing, trying to put their organization on top."
Williams has no doubt exhausted himself. After spending a club record $127 million on a team that went 79-83 and finished in third place last season, he is now a genius largely because the same players -- Adam Dunn, Jake Peavy, Alex Rios -- who made him look the fool last year have turned things around. But in pushing for the postseason, Williams' theft of Kevin Youkilis from the Boston Red Sox, and trades for Brett Myers and Francisco Liriano, only enhanced his reputation as a gambler.
"People say that, but we take great pains in having conversations that are sometimes overanalytical in making our decision -- sometimes on the sabermetric side, when we get a gut feel and sometimes on the scouting side -- but more often than not, it is a blend of those," he said.
Whichever the case, the Sox have drawn the attention and admiration of baseball observers for seemingly pulling off the most difficult of feats, that being rebuilding without being awful in the process.
"That's extremely hard to do. There's no time to reset the clock," said Yankees GM Brian Cashman. "What Kenny has done for the most part is attract players who have significant tools. He got Matt Thornton off waivers, (Chris) Sale in the draft, Jose Quintana, traded for Gavin Floyd, took a gamble on Rios, stuck it out with Peavy. He bet on the resurgence of Youkilis. Not every move you make is going to be successful, but Kenny is not afraid to make moves, to shake it up to make things happen.
"He took a chance on Dayan Viciedo. We liked him, but we didn't like him as much as the White Sox did. We thought he was really a first baseman and DH and they have him slimmed down and playing outfield, and he has 17 home runs to show for it. They did the same thing with Alexei Ramirez. They liked him a lot more than we liked him and that type of move has worked out for Kenny. He has taken what appeared to be small moves and over time has made them bigger ones."
When Williams first uttered the word "rebuild" last winter, no one listened to what came afterward: "When I said it's not going to be a domino-falling effect," he said. As he talks about it, it becomes obvious that whether they want to or not, the Sox use the Cubs as a constant barometer.
"We have two very distinct markets here between the Cubs and ours," Williams volunteered, "and I don't think we can reasonably expect our fan base to be as tolerant of a complete rebuild as the other side of town. But here's the rub. Even with that, if we felt something was the right thing to do we'd absolutely do it. The stars just didn't align that way this past offseason, so we had to do a hybrid rebuild."
Atlanta Braves team president John Schuerholz, longtime GM of the Royals and Braves, said it's tougher than it looks.
"Most capable GMs can put a winning team together and Kenny did that," Schuerholz said. "Where the real challenge comes in is the sustainability of the team you construct year after year after year. Signing, drafting, the free agent market, all those things are cyclical, and it seems like the well-run organizations make those cycles more concentric. They don't last as long when it's going badly.
"When you do that, the perception of people who watch you, most important your fans, sponsors and advertisers, recognize that this GM knows what he's doing. He knows how to deal with the inevitable downturn of the team and seems to make the appropriate moves to repair the whole cloth of the team that makes it not just as good but better."
Schuerholz goes on to stress the importance of your "cadre of idea generators," and certainly Williams is exceptionally lucky to still have assistant Rick Hahn by his side and not running some other team. Still, it was Williams, who includes among his personal tenets that he understands what he doesn't know, who first threw Robin Ventura's name into the managerial discussion last offseason, drawing a prolonged moment of silence in the room before the reaction warmed.
"No question about it," Cashman responded when asked if Williams is the leading candidate for Executive of the Year. "His team wasn't supposed to be in the conversation, and he made a controversial decision in hiring Robin Ventura, who had never managed or coached. We had the gift of having Robin in New York for one year, and he's an incredible person, so I can see what Kenny already knew. But that was a bold move. Again, he's not afraid to make the tough decision."
Williams is quick to point out that he does not have complete autonomy and that team chairman Jerry Reinsdorf has the last word, "in particular when it comes to the dollars spent on the club.
"I enjoy greater flexibility than some," Williams said. "But he's a very smart man and is the best question-asker I've ever been around. You've got to present your case and once you do, you have to stand behind it and put your name behind it."
Those who know Williams describe a noticeable softening of the edges lately, and it is no coincidence that personally, it has everything to do with his relationship with Zoraida Sambolin, a CNN anchor and formerly the morning anchor at WMAQ TV-Ch. 5, who he has been dating for a year and a half.
"On the personal side of things, I'm stable to the point where I've never been happier than I am now," Williams said. "I have a great partner who's just the most amazing woman I've ever met, so it's all good there."
Professionally, the Stanford grad, career .218 hitter and fourth-longest tenured GM in baseball can no doubt focus a little better in the absence of the drama generated by the frequent feuding with former manager Ozzie Guillen over the last few years.
But pleased? Probably not going to happen despite No. 13 on Gen. Powell's list: "Perpetual optimism is a force multiplier."
"On the professional side, I don't think I'll ever get it right because I have a football mentality in sports," he said. "It tripped me up as a player and it trips me up as an executive because I watch 162 games for our club and it's like watching a football game. The intensity on the inside wears on you, breaks you down mentally and you have to find ways to recharge yourself, but I just don't think I ever will.
"Whatever that day is that I'm shown the door or walk out myself, I'll still be saying the same thing -- there's got to be a better way."