Sergio Santos gets one last shot at making it in the majors as a shortstop
1900
The still-minor league White Sox purchase second baseman Dick Padden from the Washington Senators. In truth, Padden was sold to Detroit, but in some transaction lost to time, Padden ended up on the South Side, as the White Sox’s first player-manager. (Charles Comiskey is regarded as the 1900 team’s manager, but player-managers were the norm at the time, so at most the two men co-managed the White Sox.)
Padden, then 29, had his best season — unsurprising having moved “down” from the National League to the then-minor American. He hit a career-best .284 with another career high, 36 steals, while playing in 130 of Chicago’s 135 games.
Oh, and Padden led the White Sox to the first AL pennant, with an 82-53 record.
When the White Sox moved into the major leagues in 1901 and enticed pitching ace Clark Griffith to jump to the AL, part of the proviso was granting Griffith the manager’s role. Thus Madden re-jumped back to the National League, and the St. Louis Cardinals.
2006
The White Sox pull off what turns out to be a terrific deal, in a swap of blue-chippers. Seattle sends its ballyhooed southpaw Matt Thornton to Chicago for outfielder Joe Borchard.
Borchard was a first round (No. 12 overall) pick in 2000 but beyond hitting what is still the longest home run in new Sox Park history (504 feet) in 2004 never had a single positive-WAR season. He lasted for six games in Seattle before being placed on waivers in May.
Thornton, the No. 22 overall pick in 1998 by the M’s, fell under the tutelage of pitching coach Don Cooper, conquered his control issues, and became a dominant reliever for the better part of a decade. Right away, he contributed to White Sox success, with an outstanding 1.7 WAR and 3.33 ERA in 2006. Over his seven-plus years in Chicago he tallied a 3.28 ERA/3.02 FIP and 10.8 WAR over 512 games, and was named an All-Star in 2010.
2009
The White Sox swapped shortstop Sergio Santos — signed as a minor league free agent on January 12 — to the San Francisco Giants. Whether explicitly plotted or not, this deal seemed to be predicated on giving Santos one final shot to make it in baseball as a hitter. Support for this hypothesis comes in the form of Santos failing to make an impact with San Francisco at the end of Spring Training and getting shipped back to Chicago on April 1 — at which point his transformation from hitter to relief pitcher began.
Just one year later, Santos broke north with the White Sox — as a key setup man in the bullpen.