Take as an example a question asked to Guillen prior to Sunday's Game 3 of the American League Division Series concerning his choice for the best team in baseball.
"I think the best team in the American League to be honest with you in Spring Training was the Seattle Mariners," said Guillen with a smile. "Just look at the team in Spring Training, and wow. Good ballclub."
Seattle finished with 101 losses and the second-worst record in baseball. None of Guillen's remaining decisions were remotely as close to off the mark. And Guillen had plenty of controversial calls to make in a season filled with mishaps and inconsistent play.
The White Sox went through the final month of the 2008 campaign without Carlos Quentin, Joe Crede and Jose Contreras due to injury. Quentin was a bona fide Most Valuable Player candidate at the time he broke a bone in his right wrist, and Crede, stopped short by back problems again, has proven to be one of the better clutch hitters in recent franchise memory.
That ability with the game on the line certainly would have come in handy Friday, when the White Sox stranded 12 runners. As for Contreras, he stands as the most playoff-tested of all the White Sox rotation. It would be easy to use these injuries as an excuse, but the team somehow fought its way into the postseason.
Guillen was the one who set the tone for the team's survival.
"There was no doubt it was going to be harder to do what we want to do," said Guillen of the injuries. "It's tough, though, because you go by what the leader says. If I was going to say, 'Oh God, those guys are down,' well now they can use that thing to cover [themselves] and say, 'Well, this is why we lose.'
"No, that's why I said we want them, but we don't have them. We had people out there that could still do the job, and they did it."
On-the-field problems such as those mentioned above were piled on by off-the-field problems, according to Guillen. Those issues ranged from the blowup doll controversy in Toronto to Guillen speaking out against his offense in Tampa Bay, to his shortstop calling up to the pressbox to have a call changed and the ensuing ramifications from that decision.
"Tough season for me. Real tough," Guillen said. "I think tougher than 2007, when we really were bad."
Navigating these choppy baseball waters should get Guillen's name mentioned in the Manager of the Year discussion. But Guillen himself said Tampa Bay's Joe Maddon is the hands-down choice to win in the American League, and by his estimation, Minnesota manager Ron Gardenhire did the best job overall.
Ultimately, Guillen only remains concerned with wins and losses. Even surviving his toughest of five seasons at the helm, Guillen isn't worried about falling into the managerial genius category.
"To me, it's easy to manage when you have a good ballclub. It's easy to manage when you win 120 games," Guillen said. "The players make you good or bad. This was the hardest year for me, as a man, as a manager. There were a lot of problems off the field, on the field.
"People say that in 2005 I [won] the AL Manager of the Year. To me, it was like, if  is managing, I want to manage every year. That wasn't managing. That was a good ballclub. They put everything together. But this year, we make three lineups one day. Every day, something was going on. Injuries and problems. Off the field, stupid things.
"I don't live for being considered a good or bad manager, genius or that. As long as 25 guys out there know what I can do, that's all I care about. At the end of the career, the only thing that matters is who wins the most games. Right now, I'm climbing. Some guys are already there, but I don't have to prove to anyone how good or bad I can be."
Scott Merkin is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.