So it only made sense that his White Sox would square off with the Rays in the American League Division Series, which the South Siders lost in four games, ending with a 6-2 defeat Monday.
"I feel proud to be the first manager to start against that team in the playoffs," Guillen said after winning the one-game playoff with the Twins a week ago. "They know how I feel about them. And you guys that have been with me all year know how I feel about that organization."
"They played better than us, there's no doubt," said Guillen, who congratulated the Rays in his opening remarks during the postgame press conference. "They pitched better, they executed better, they got big hits, and I tip my hat to them because they outplayed us."
White Sox general manager Ken Willams was impressed not so much by the fact that the Rays won, but the way in which they got to this point.
"They've done it right," Williams said. "They've done it through the Draft and made some very wise choices. People think the Draft is easy, but it's not easy. A lot of teams have gotten No. 1 picks because of their status over the years, and they've been wrong."
When asked how his opinion of the Rays might have changed from Opening Day through Monday's loss, Williams simply said: "It doesn't matter. They're the champions."
So far, the Rays are only the champions of the American League East. But the future -- both long term and short -- looks bright.
White Sox captain Paul Konerko compared Tampa Bay's style of baseball to the 2005 White Sox, who went 11-1 in the postseason and won the World Series.
"But I think they might have a little more of a consistent offense than we had," Konerko said. "I think you can get by the fact that it's their first time in the playoffs. If they don't let that stuff distract them, I think they'll win. I think they got the best team all-in-all. They got something special going over there, and we tip our hats. They beat us."
"It's good for baseball to have a team like Tampa win," White Sox chairman Jerry Reinsdorf added. "It's too bad that they beat us, but it's really good for the game."
David Just is an associate reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.