He hit the target in 2005. But as Williams watched the Blackhawks celebrate their third Stanley Cup title since 2010 with Thursday's parade and rally, the White Sox executive vice president had to admit to being a little bit envious.
"[Heck] yeah. Jealousy," said Williams with a resigned smile. "I wanted that for this franchise.
"And it wasn't for lack of trying. As a matter of fact, it's funny a lot of the criticism I've gotten over the years has been for trying too hard maybe to get back there. If you are not trying to get to that stage, I really believe you should be doing something else with your life."
The Blackhawks, who colorful White Sox television play-by-play announcer Ken "Hawk" Harrelson called the most exciting team in sports, stand as a model for teams to follow. They constructed a good young corps of players, let them lose and develop together before adding key veterans so help them win.
In order to get those top players, though, teams usually go through some lean years. Williams had only one truly bad season, in 2007, during his tenure as GM and just one Top 10 Draft pick in Gordon Beckham in 2008.
"Sometimes in order to get those really top-of-the-line, you know, higher-impact-type guys, you see them go to a lot of teams that finish last in the standings," Williams said. "We just haven't been that, we've had some tough seasons but I guess you can say we haven't had enough of them."
General manager Rick Hahn has been in charge of the White Sox title push since 2013 and has built a solid young core. The team looked on paper to be a true contender going into 2015 but hasn't lived up to that hype to date.
Meanwhile, the Blackhawks were celebrated throughout the city on Thursday and at U.S. Cellular Field that night. Williams knows Blackhawks owner Rocky Wirtz and President and Chief Executive Officer John McDonough and is happy for the entire organization. He just always envisioned the White Sox having the same type of success.
"I can't be happier," Williams said of the Blackhawks. "I'm not saying I wish it was us rather than them. What I'm saying is I wish it was us too."
Scott Merkin is a reporter for MLB.com. Read his blog, Merk's Works, follow him on Twitter @scottmerkin and listen to his podcast. This story was not subject to the approval of Major League Baseball or its clubs.