If the White Sox were to claim that second crown, a multiple-championship goal Williams talked about when he was first hired by Jerry Reinsdorf as the franchise's 11th general manager on Oct. 24, 2000, and has repeated countless times since, then he could be going out on top in more ways than one. Not only would the South Siders be king of the baseball world, but they would do so behind one of the more perfectly laid-out seasons in recent memory by Williams and his front-office staff.
This campaign has been defined by a see-a-problem, fix-a-problem sort of mentality shown by Williams, assistant general manager Rick Hahn, vice president of player development and special assignments Buddy Bell and company. There has been very little lag time from the point of struggle to promotion or acquisition of a solution, from within the system or from outside the organization.
It's the same sort of go-for-it-all approach Williams has employed for the entirety of his 12-year tenure, acquiring 171 players via 72 trades. That total includes third baseman Kevin Youkilis and right-handed reliever Brett Myers, who have directly and positively influenced the 2012 White Sox first-place standing in the American League Central, acquired without Williams mortgaging the present or the future. These moves become the offshoot of years of planning, in some cases, as opposed to a knee-jerk reaction to counter another team's success.
"I've asked questions about particular players of interest who may not be available for another two years," Williams said. "So by the time I have all the conversations with the people, it may be one of our Minor League managers or hitting coaches or the whole staff that's seen the guy play two, three or four years ago, all the way up until now where he's on a greater radar screen. And you've seen a radar screen?
"That starts out as a small blip and the sound, the sonar, gets a little louder, a little louder. Something happens and we need him, and it's not a scramble to try to find someone."
Not every chance taken by Williams warranted an A+ grade. Some wouldn't have even been passing.
When the White Sox needed an offensive jolt for the 2010 postseason push, the team claimed Manny Ramirez off of waivers from the Dodgers on Aug. 30. Ramirez hit .261 with one homer and two RBIs on the South Side. Neither of the trades involving Nick Swisher would go at the top of Williams' resume.
Francisco Liriano was picked up from the Twins prior to the non-waiver Trade Deadline this season as a way to extend the rotation and protect the innings totals of first-year starter Chris Sale and rookie Jose Quintana, but also because Williams felt the southpaw could help take the White Sox from division contender to championship level. A struggling Liriano has shuttled between the bullpen and rotation this past week.
Some of those moves look perfect on paper, but they can take a little while to materialize. See Adam Dunn's 38 homers and 88 RBIs this season before being slowed by a strained right oblique, after last year's disaster as a free-agent acquisition, as an example. As much as the Executive of the Year talk has surrounded Williams in 2012, he knows it doesn't take much for that court of public opinion to change.
"Same [front-office] staff, same thought process, same aggressive energy that we've always had to try to improve the club," Williams said. "What's the difference between being the village idiot in Chicago last year and this year? The players' performance.
"This is all about them. It's all about the coaching staff and it's all about the fans. At this level, I consider us kind of a steward for all of them. And I don't take it personally and I understand when ... . I can see when I'm about to become the village idiot before you can see it. Here it comes."
Prognosticators had the White Sox as a 2011 playoff team, so the "village idiot" depiction came from the underachieving 79-83 performance. The current group has overachieved by many accounts outside the White Sox clubhouse, leading to the plaudits for Williams.
According to Hahn, who has worked with Williams for 12 years as a highly thought of baseball executive in his own right, nothing has really changed as far as approach between the two seasons.
"Ever since Kenny has been in the big chair, he has made it clear we want to be aggressive and creative in trying to solve problems," Hahn said. "When we were sitting there in mid-February, we weren't counting on certain names that have contributed to contribute.
"Again, it's sort of the mindset that he sets in terms of, 'We need a solution for this. How are we going to go about doing it?' We've been able to get creative."
Adding elite talent stands as an important part of Williams' plan. As Williams has grown on this job, he also came to realize the fit is as important as the ability.
In the case of Youkilis, Williams didn't ask his valued scouts and staff what the third baseman had left in his bat or with the glove. Williams wanted to know if Youkilis still had the fight he had shown previously.
As for Myers, Williams wanted another "tough son of a gun" who had experience closing, could mix in all his pitches and throw them any time in the count, while lending another veteran arm to a youth-laden bullpen. Dewayne Wise, who returned to the White Sox as a Minor League free agent after being released by the Yankees, has provided starter's value in a projected extra outfielder's role.
Making those improvements doesn't go unnoticed by a team fighting for the postseason.
"That's an awesome feeling knowing they are here for us and not just content with how we are doing," White Sox closer Addison Reed said. "It's good to know they have our back, and they can really see and appreciate how hard we have been playing and kind of return the favor."
"One wrong move and you can destroy your team, so you have to be cognizant of so many different variables," Williams said. "But sometimes an infusion of a guy that might not be the most popular guy around can actually help you. It just depends on what the rest of the makeup is of your team and how strong you are in character to ride through."
Williams operates under an all-inclusive management style, and according to Hahn, he wants to be challenged and welcomes alternative viewpoints brought to the table. The sum of those viewpoints resulted in a team sitting on the playoff cusp with just 19 games remaining.
Another championship run could mark Williams' last at the White Sox helm, or so he humorously hinted, although it would be hard to imagine another job that could drive and challenge him as much as this one, or mean so much personally.
"He's got a world of opportunities," said Hahn of Williams' future. "But that's a personal decision."