Although Guillen has received a great deal of notoriety for his continuously colorful depictions of his team, and, often, his analysis of individual players, the leader of the South Siders certainly has impeccable baseball credentials and the vast knowledge of the game's intricacies necessary to handle this new role. He played 16 seasons in the Majors and took part in six playoff series, including a 1999 World Series loss to the Yankees when he played for the Braves.
A talented shortstop, Guillen was a three-time All-Star and received an American League Rawlings Gold Glove in 1990. But his fame and fortune have come more from his highly acclaimed six-year stint as the White Sox manager than his production on the field.
Guillen lead the White Sox to a World Series title in 2005. Chicago beat the Astros in four games, completing an 11-1 postseason run to the championship, a lofty mark that the Yankees could equal this year with five more consecutive victories.
It was Guillen who picked the Yankees to win it all this season when asked for his prediction during the final week of the 2009 campaign, as the White Sox were finishing their schedule in Detroit.
"I have to go with New York because of their pitching staff, and they're hungry. They want to be there," Guillen said. "The ballclub is very solid. But you never know. I remember going to the playoffs when St. Louis was the worst team in baseball, and they won the championship.
"When you get in, you don't know what's going to happen. [On] paper, I think New York looks better. They got three guys who are pretty good pitchers, their bullpen is pretty strong and their lineup is pretty strong. You don't win that many games just because."
The eldest of Guillen's three sons, Ozzie Jr., recently completed his fifth season as one of the Spanish-language broadcasters for White Sox games. He begins similar work with the Chicago Bulls on Nov. 13.
Scott Merkin is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.