Maybe it won't quite be an ear-to-ear grin, as he flashed in late October 2005, when the White Sox won their first World Series title in almost 90 years, or during the ensuing celebratory parade in front of approximately 2.5 million people in Chicago. But it should be a knowing smile of satisfaction.
Not only has Williams added possible impact players such as Jake Peavy, Alex Rios and Mark Kotsay to an already solid team in pursuit of an American League Central crown, but he has done so by bringing in more than the proverbial guns for hire in an attempt to win a division. These are players who will help in the present but also maintain the franchise's strength for years to come.
Yet, when this six-game homestand began on Monday against the Royals, the White Sox general manager certainly was not focusing much on how wisely he had set up the White Sox for future seasons.
"Right now, I'm really not happy with what I've seen," Williams told MLB.com, focusing on the second-place White Sox, who he firmly believes should be nothing short of a division champion. "It's difficult for me to be too excited about tomorrow when today is not being taken care of.
"So, as I have played with different thoughts about 2010, I really like this team as it is presently constructed, more than I've liked a lot of [past] teams that have had more success up to this point. I really like where we are and where we are headed and what's coming up from the farm system.
"I like a lot of elements to it. I love the balance, the flexibility, the pitching, the defense is getting better. It's a more athletic team," Williams said. "In my mind, I don't know if we are going to achieve enough success this year or ultimately have the resources, but I would love to bring back this whole darn team."
That "success" barometer has been invoked on a few occasions by Williams since adding the $52 million left on Peavy's deal over the next three years and bringing in the remainder of Rios' seven-year, $69.835 million contract, starting in 2008 and running through 2014, via last Monday's waiver-wire claim. The White Sox had done extensive research and fact figuring to make sure they could take on such a salary increase, but the way this present team ultimately performs will influence if valued potential free agents such as Jim Thome or Jermaine Dye possibly could return for 2010 and beyond.
In order to better understand Williams' mindset, he was asked to define 2009 success. Is it simply a winning, competitive season or is success a second straight division title? Anyone who knows Williams realizes success, for him, is laid out as nothing short of another World Series crown.
"It's all I can see," Williams said. "I don't know that anything less [is good enough]. At the end of the day, you are either the last man standing or you are not. The greater your successes are, the greater your chances are for all the resources you need to have a team that you really want to put out there.
"If the end result isn't success," Williams said, "you have to look for another way."
Keeping the same team together is appealing to an entrenched veteran such as starting pitcher Mark Buehrle, who has been with the White Sox since 2000. He also realizes that rarely, if ever, does the same exact group return from year to year, but knows that through the work of Williams and his staff over the past few years, there won't be as much upcoming turnover within the White Sox.
As for Williams' comment concerning his deep connection to the 2009 squad, Buehrle could relate to part of Williams' feelings.
"Just away from baseball, as far as the core group in the clubhouse, the personalities of the guys and the families, it ranks up there with some of the better ones," said Buehrle, who has been a part of every one of Williams' nine teams. "But I hate to compare them on the field just because we haven't done anything here yet."
Even if the White Sox don't match 2005 and can't bring back the whole group, they have a strong core already in place, mixed with veterans and rising young talent such as John Danks, Gavin Floyd, Carlos Quentin, Gordon Beckham and Chris Getz. Williams certainly won't be force to overpay, in his estimation, while dealing with the offseason open market.
And while the White Sox have not had the greatest success in pursuing high-end free agents in the recent past, with Torii Hunter's name coming to mind, Williams certainly isn't ruling out that particular venue for future improvement. He isn't ruling out any manner in which to make the team better.
"Well, there's more than one way to skin a cat," Williams said. "Yes, there have been a couple of times where we've gone after people in free agency, and for a variety of reasons, we did not end up with the guy. So, you have to look at other avenues -- free agency, such as a Cuban guy like Alexei [Ramirez], or a trade, or in the latest case, a waiver-wire transaction.
"You try to make your team as strong as you possibly can, however you can. You get talent in however the [heck] you can. Sometimes you have to pay a premium in terms of where it's the talent you give up and sometimes you pay a premium in terms of the dollars that you give up. I like the idea of getting talent the last manner [in Rios], in which we didn't have to give up any Draft picks.
"Would I prefer where we were able to work something out where we brought down some of the money so we had future flexibility? Absolutely," Williams said. "That's no secret. But you know what? I wish everybody was making less. I would like to pay everyone a little less."
Williams paused, with a smile, before once again tying in 2009 to the financial future.
"Win," Williams said, "and we don't worry about that."
Scott Merkin is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.