But the times have changed for Konerko, as have the different stages of his career and his life, and of course, the overall economics.
"At that time, I didn't know what was going to happen," Konerko said. "That was five years ago and it's totally different now. You change as a person. At the time, I had a wife and a month-old baby.
"Now I have a wife, a 5-year-old kid and a 2-year-old kid. Things change along with that. Everything that was involved -- all the moving parts to it -- that were in my life then, was to come back here.
"Where it will be this time around, I don't know. We'll have to find out as we go. It definitely isn't just that you've been in one place for a long time or the number of years in a contract, the money. There's so many little factors to it. It's not all one thing. There are always little pieces that fit into it."
That last free-agent agreement for Konerko worked out to $60 million over five years. He certainly held up his end of the bargain and then some during that time, serving as the pragmatic conscience of manager Ozzie Guillen both on the field and in the clubhouse.
Much like Konerko's stellar effort in 2005, when he hit .283 with 40 home runs and 100 RBIs, he once again illustrated how a potential walk-away year should be handled in '10. Konerko stands as a frontline American League Most Valuable Player Award candidate, with a .310 average, 38 home runs and 107 RBIs.
Those numbers, and simply his 12-year presence on the South Side of Chicago, have fans clamoring for Konerko to finish his career with the White Sox. General manager Ken Williams recently told MLB.com how he wants Konerko to retire as a member of the White Sox, but explained the situation couldn't fully be talked about until the close of the current campaign.
On Thursday, Guillen reiterated his desire to have Konerko stay with the White Sox, but the manager also understands he can't always get what he wants.
"Kenny knows and [White Sox chairman] Jerry [Reinsdorf] knows what Konerko means to this organization," Guillen said. "But besides Konerko in this organization, Frank Thomas was here, Harold Baines was here, Ozzie Guillen was here. That's the situation, you've got to take it with your heart or your brains.
"When you think with your brain, you make mistakes. When you think with your heart, you make mistakes. There's no doubt in anybody's mind they want him to be back here. Money-wise, that's another problem.
"Do we want it? We all do, there's no doubt," Guillen said. "Hopefully they get something done; we'll see what happens. That's a very, very delicate thing -- a unique situation."
As far as Konerko is concerned, money is not the sole factor in this next phase of his career.
"It's about the game," Konerko said. "It's not so much about the contract or the years or the money. It could be that I get more here and don't come back. You know, I got a family to think about. I got, you know, how do I fit in on a team?
"There's a lot of things that go into it. It's not about I've made a lot of money in this game, and it's not all about that. At the same time, when it gets to those situations, it's always been that the player has to take the discount, never the team going above to get him back. You see it from all angles.
"Just to say I'll take a discount, I would never say anything like that. And I'm telling you it could be a better deal than anyone else's and I decide to go somewhere else because of what I'm feeling for myself and everybody involved in that moment. That's the honest truth."
Due to a change in offseason procedures, the White Sox will have five days after the World Series to exclusively negotiate with Konerko. But even if Konerko ultimately moves to another locale, his career contributions dotting various White Sox all-time lists on offense will make him a permanent part of the franchise.
Launching a grand slam in Game 2 of the 2005 World Series sweep helps cement that legacy.
"His number's going to be retired, he's going to have a statue here," said Guillen of Konerko, who said he would be willing to serve as a designated hitter, even though he still is more than capable at first base. "If you look at PK's numbers and what he means to this organization, that's a pretty tough situation for everyone."
"Obviously it's a business, so they have to figure out payroll stuff, and when they do that, then hopefully I'm in their conversation, as far as being brought back," said Konerko of the White Sox. "Until then, I don't know what will happen. I just want to do what's right. At this moment, I don't know what that is. I don't know what I want."