The White Sox and Chicago Cubs have not traded very often in the history of both franchises and most of the trades are forgettable, but with the Aramis Ramirez talk there are a few in my lifetime that are definitely worth mentioning. Well, two to be exact.

1998: Cubs trade Jon Garland to the White Sox for Matt Karchner
The trade that would alter Chicago

baseball history to the point that Andy McPhail would have liked to have jumped into a Dolorean to fix this mistake in 2003. McPhail was President at the time when GM, Ed Lynch, was desperate to add a righty reliever to the contending Cubs bullpen.

The right arm the Cubs would add to their bullpen was at best average reliever, Matt Karchner, from the White Sox in exchange for the Cubs 10th overall draft pick from the 1997 draft, Jon Garland. Karchner had posted a 5.15 ERA with 11 saves for the White Sox, so when the Cubs came calling the Sox were happy to oblige. The Sox were looking to the future so they asked the Cubs for their first round pick, Jon Garland in exchange.

It’s shocking to me that Ed Lynch was that desperate and dumb to trade away so much talent for such mediocrity, especially since Garland was a first round draft pick. If Garland had been a later round pick that blossomed into greatness then it would have made more sense.

In 2003, the Cubs had one of the better rotations in baseball with Mark Prior, Kerry Wood, Matt Clement, and Carlos Zambrano, but they also had Shawn Estes and his 5.73 ERA. It’s safe to say that Jon Garland would have been a starter in that rotation, and may have helped the Cubs get to and win a World Series.

In 2005, Jon Garland did that very thing for the Chicago White Sox, as the Sox went on to win the 2005 World Series lead by an incredible starting rotation.

1992: Sox Trade Sammy Sosa and Kenny Patterson to the Cubs for George Bell
This turned out to be the worst trade of all-time for both clubs, as time would tell. Sammy Sosa was traded in 1992 because he wouldn’t adjust his approach to hitting under legendary hitting coach, Walt Hriniak’s instruction. Sosa started the 1992 season by hitting two home runs on Opening Day for the Sox. I remember thinking that he was finally going to be the player that the Sox traded for, unfortunately that was the highlight of his shortened season with the Sox.

Thanks to steroids Sosa turned into one of the premier sluggers in baseball, while a non-steroid aided Frank Thomas became a Hall of Fame hitter under Hriniak’s tutelage.

Still, I went to Wrigley a lot during the home run chase of 1998 between Sosa and Mark McGwire and had great time watching the spectacle take place. Sox fans hated Sosa, not for any reason other than we all felt like the Sox let a good one get away.

The reason it’s the worst trade in the history of trades between the Sox and Cubs is because it’s the only trade that ultimately backfired for both sides of town.

George Bell was more worried about his gas station in the Dominican then playing baseball, and was a total bust for the Sox.

Meanwhile, Sosa had every chance to be the next Mr. Cub, but poor decision making on Sosa’s part turned him into a pariah around Wrigley Field. The once adored player is now just a bad memory that ended with Sox fans getting the last laugh.