Guillen later managed the Chicago White Sox from 2004 to 2011, winning the World Series in 2005 and then moving to the Miami Marlins in 2012.

As a player, Guillén was respected for his passion, speed, hustle, intensity and defensive abilities and his ebullient love for the game.

[1][2] In 2005, Guillen became the first Latino manager in major league history to win a World Series when he captained the Chicago White Sox to their first championship in 88 years.

Guillén was a light-hitting, quick-handed shortstop, emerging from a line of Venezuelan shortstops that included Chico Carrasquel, Luis Aparicio (both White Sox players), Dave Concepción, and Omar Vizquel (who played for Guillen as a utility player for the White Sox).

[7] When the next batter hit an infield single, Guillén never hesitated as he rounded third base, catching the Yankees defense off guard and scored the game-winning run.

[10] The injury caused him to miss almost the entire season, and subsequently diminished his defensive range as well as his stolen base output for the remainder of his career.

[13] He hit .273 and scored four runs in the 1993 American League Championship Series as the White Sox were defeated by the Toronto Blue Jays in six games.

[11][14] In October 1997, after 13 seasons with the White Sox, Guillén was granted free agency status and signed a contract to play for the Baltimore Orioles.

[17] After playing one year with the Tampa Bay Devil Rays in 2000, he retired as a player at the end of the season at the age of 36.

[11] Guillén's .974 career fielding percentage ranks him 40th overall among major league shortstops, ahead of, among others, of both Luis Aparicio and Dave Concepción.

This trio would win every American League Gold Glove for a shortstop from 1986 until 2001, with the one exception being Guillén's 1990 season award.

[20] As a hitter, he was known as a free swinger, posting one of the highest at bats per walk ratios in major league history and also had one of the lowest on base percentages for many of the years he played.

[21] Guillén played his entire Venezuelan Winter League career with Tiburones de La Guaira.

In 2005, he led the White Sox to their first American League pennant since 1959, and their first World Series win since 1917 with a four-game sweep of the Houston Astros.

In November, Guillén was voted the 2005 American League Manager of the Year Award by the Baseball Writers' Association of America.

[33][34] In February 2016, Guillen was hired to manage the Tiburones de La Guaira of the Venezuelan Professional Baseball League for the 2016–17 season.

In 2022 he was named bench coach for France in the World Baseball Classic, joining the staff of manager Bruce Bochy.

[48] On April 10, 2012, Guillén was suspended for five games by the Marlins due to comments made about former Cuban president Fidel Castro.