:format(webp)/cdn.vox-cdn.com/uploads/chorus_image/image/70393794/2368379.0.jpg)
2003
Another bold stab by GM Ken Williams came as he acquired starter Bartolo Colón as part of a three-way deal with the Montreal Expos and New York Yankees.
The Yankees first sent Orlando Hernández to the White Sox for Eddie Candelario and Antonio Osuna. The White Sox flipped El Duque to Montreal along with Rocky Biddle, Jeff Liefer and cash for Colón and Jorge Nuñez.
Colón had a good 2003 season for the White Sox, with 15 wins, 242 innings pitched and 173 strikeouts. It was his walk year, so he parlayed his South Side audition into a four-year, $50 million deal with the Angels — with whom he’d win the Cy Young in 2005.
Williams brought Colón back in 2009 hoping for the same, but got little for his troubles. In fact, Colón got hurt, was overweight and when assigned to a minor league rehab stint never reported! It was rumored that Colón was distraught over the death of Michael Jackson, and when manager Ozzie Guillén heard such he emptied out Colón’s locker and dumped the possessions in the hallway outside of the White Sox clubhouse.
(Williams would also bring back Hernández, almost exactly two years after this trade flip, and El Duque would be a pivotal part of the 2005 title season.)
2021
The White Sox continued to make strong moves to get back into serious contention for a championship, announcing the signing of Liam Hendriks, one of the top relief pitchers in baseball, to a multi-year deal. Since taking over as the A’s closer on June 21, 2019, Hendriks had recorded a 1.99 ERA over 68 innings pitched, with 39 saves, 111 strikeouts and a 0.79 WHIP in 65 appearances.
The “creative” contract netted the Australian righthander $54 million over as few as four years, with an unusual twist, perhaps the first of its kind in baseball. The fourth year of the deal had an option year, worth $15 million. If the White Sox were to decline the option, a $15 million buyout would be paid in 10 equal installments between 2024 and 2033. (Deferred money, something NFL teams often do, could help with the luxury tax threshold should the Sox be in a position where it becomes an issue.)
Hendriks didn’t disappoint in the first year of his deal. He posted 38 saves, a 2.54 ERA and 113 strikeouts against only seven walks in his first year on the South Side, winning AL Relief Pitcher of the Year honors.