1931
The White Sox changed outfielders Carl Reynolds And John Kerr to Washington for second baseman Jackie Hayes and jars Bump Hadley And Sam Jones.
Hayes played the remainder of his days with the White Sox, compiling 6.1 WAR over nine seasons, with real standout campaigns in 1933 and 1936. “Sad Sam” also finished his career with the White Sox, starting for four seasons (8.5 WAR total) before retiring after the 1935 season at age 43. Hadley enjoyed an excellent career, but pitched only three games for the South Siders in April 1932 before being transferred to St. Louis.
Reynolds went to Washington and had a solid year (equal to Hayes’ best) before being shipped to the Cardinals in a deal for Goose Goslin. Infielder Kerr was a substitute for the Senators for three seasons before his career ended. He played few consequences, but saw action in one game in the 1933 contest. World series.
Ironically, exactly nine years later after this trade, the White Sox released Hayes, who lost the sight in his eyes due to glaucoma.
1957
New Cleveland GM Frank Lane made his return to the American League with a splash: in a trade that shocked and outraged many White Sox fans, the popular outfielder was Minnie Minoso and infielder Fred Hatveld were traded to Cleveland for the future Hall-of-Famer Wynn asked and outfielder Al Smith. Wynn was coming off the first losing season of his career, but would lead the AL in wins and innings pitched in 1958. He and Smith were among the last pieces acquired for the 1959 pennant-winning franchise. Wynn won the Cy Young that season, with 22 wins, and Smith was a solid contributor for the Sox until he was traded before the start of the 1963 season.
1973
It was just one of many trades between the White Sox and Jalisco Charros (Horsemen) of the Mexican League, but turned out to be one of the best: Chicago sent a shortstop Rudy Hernández back to Mexico in exchange for starting pitcher Francisco Barrios and minor league reliever Manuel Lugo. Barrios would make it to the majors for good as a swingman in 1976 and was the top starter (4.4 WAR) for the vaunted 1977 South Side Hit Men. He remained a loyal rotation through 1978 before injuries began. Overall, Barrios was an 8.4 WAR pitcher with a 4.15 ERA/4.05 WHIP over just 129 games in the majors – solid, by any definition.
1980
Owner Bill Veeck played the legend coaching card again and hired a top batsman See Pinson as hitting coach for 1981. The lefthander played 18 years in the bigs and had five-tool talent, including 2,757 hits, 256 home runs and 305 steals.
Pinson was just 42 years old when he was hired and just five years removed from his playing days. Given the solid but uneven play of the 1981 White Sox, perhaps Veeck was considering activating the legend.
1990
In an ill-fated attempt to add more punch to the lineup, the White Sox sent Erik King And Shawn Hillegas to Cleveland for Cory Snyder and minor league shortstop Lindsay Foster.
It wasn’t that King or Hillegas were excellent in 1991 — though their combined 2.0 WAR would have helped in the division race — but that Snyder was unbearably terrible. Already an overhyped prospect (drafted No. 4 overall in 1984 after a stint with Team USA), Snyder was a player who only played slug and barely managed to be a positive asset with the bat overall. In just 50 games with the White Sox, he hit the ground running for -0.5 WAR before being dumped to the Blue Jays in July.
1997
Jerry Manuel was named the new White Sox manager, replacing him Terry Bevington and becoming the second Black skipper in franchise history. When he was hired, Manuel had no previous major league management experience. He defeated the former White Sox shortstop Bucky Dent and Larry Parrish, among others, for the job.
In Manuel’s seven years, the White Sox made one postseason (2000) and had three winning seasons. He would be named Manager of the Year for his efforts to conquer the Central Division in 2000 with 95 wins.
2008
Partly due to the belief that he simply wasn’t a big-game pitcher, Javier Vazquez was dealt to Atlanta as a lefty reliever BooneLogan for catcher Tyler Flowersinfielder Brent Lillibridge and minor-leaguers Jon Gilmore (third base) and Santos Rodríguez (relief pitcher).
Vázquez was brilliant in 2009, matching a career best (also set in 2007, with the White Sox) with 6.2 WAR and finishing fourth in the NL Cy Young voting. However, he would not play baseball again after the 2011 season.
Flowers was a promising player (No. 99 in all of baseball at the time of the deal) who had already been in trouble with a PED suspension. Over seven years with the White Sox Flowers brought almost nothing to the table offensively (84 OPS+) and saw almost all of his value in the emerging metric of the field frame.
Lillibridge was also a promising prospect, reaching No. 63 overall before making his MLB debut in 2008. He never really gained a foothold in the Majors, though after a brief but powerful breakout in 2011, he worked his way to an .845 OPS and 1.5 WAR over 97 games while playing five defensive positions plus DH.
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