Top 10 Trades of the Kenny Williams Era (Part 1)

With the MLB Trade Deadline on Thursday and the White Sox involved in trade rumors with teams from Boston to Oakland and seemingly everyone else in between, it seems like a natural time to look back on Kenny Williams' career to date. Since taking office in late 2000, Williams has been the model of an aggressive GM, willing to trade away even the most highly touted prospects for Major League talent. Considering it was Williams' plan and execution that brought the White Sox their first World Championship in 88 years, it's hard to be very critical of his work; while at times (especially early times), Williams seemed overmatched and out of his league, his recent work has, at times, been nothing short of brilliant.

So, in honor of the deals (and no-deals), brewing in the White Sox front office, here are the ten best trades KW has pulled off since his tenure as General Manager began...

TO SOON TO CALL: December 3, 2007 - Acquired Carlos Quentin from the Diamondbacks for Chris Carter.

While Quentin has been one of the major breakout stories of 2008, it's important to remember that one of the major reasons the Sox were able to pry the highly touted prospect from the Diamondbacks were questions of his durability. In two injury-shortened seasons in Arizona, Quentin never fully displayed the potential he showed at Stanford and 4 seasons in the Arizona farm system. While this deal will seemingly undoubtedly one day be in Williams' top 10 (and maybe be his best ever), with only a little over 1/2 season after the fact, it's still too early to properly gauge this deal. However, at this point, the only way it seems that this could even be considered a push, would be for Quentin to completely break down and Carter to develop into the power-hitting first baseman he could possibly become. Currently, Carter is hitting .261/27/83 for the Stockton Ports, a High-A team in the Athletics' organization (Carter was later dealed by Arizona to Oakland in part for Danny Haren), however his numbers and growth are paled by Quentin, who at the same age was already in AA and had a higher slugging percentage, with almost 20 less home runs (showing a total power package and not an all-or-nothing approach).

#10 - January 29, 2002 - Acquired Willie Harris from the Orioles for Chris Singleton

After three quality seasons in center field for the White Sox, Williams shipped then 29-year-old Singleton for Harris, and while Willie never developed into the second baseman the Sox hoped they'd acquired, he provided the team with 4 years of dependable play as a utility man and pinch runner. He also scored the deciding run in Game 4 of the World Series and Singleton only played full-time for 1 season in Baltimore and 1 more in Oakland before finishing his career in late May of 2005 with the Devil Rays.

#9 - July 31, 2007 - Acquired Jon Link from the Padres for Rob Mackowiak

If there's still one valid criticism of Williams its been his inability to turn veteran MLB players into quality young prospects during during down years, and while that's not necessarily a big problem for someone from a market like Chicago, it's still valid criticism. However, at last year's trade deadline, he was able to deal Mackowiak, an overplayed, under-performing utility outfielder/infielder (at best) for Link, a relief pitcher having a nice season in Lake Elsinore, the Padre's High-A ball team. However, in 2008, Mackowiak hasn't appeared in a Major League game since early June when he was hitting .132/.254/.208. Link has blossomed in his first full year in the White Sox's farm system. Link's notched 27 saves in Birmingham, with a 1.77 ERA and striking out just about 1 batter per inning. He was named to the Southern League All-Star Game and has become even more important with the rash of injuries and ineffectiveness that has plagued the Sox bullpen; Link may be seen sooner than later.

# 8 - March 27, 2002 - Acquired Damaso Marte and Edwin Yan from the Pirates for Matt Guerrier

After posting several solid seasons in the White Sox system, including an 18-win campaign in 2 stops in 2001, Guerrier seemed destined for, if not stardom, at least a solid career in the Majors, but days before the 2002 season started, Williams shipped Guerrier to Pittsburgh for Marte and Yan. Though Edwin's never panned out as a Major Leaguer despite stealing 88 bases in 2002 and 76 in 2003, Marte was, for the most part, a dependable left-handed reliever who peaked in 2003 when he posted a 1.58 ERA in just under 80 innings. Guerrier, on the other hand, has failed to live to his promise. Since debuting in June of 2004, Guerrier has only started 3 games, the last on September 12, 2006. True, Guerrier's been a dependable reliever, but for a guy who a few years ago seemed destined for a job in a starting rotation, you can't complain too much about giving him up.

# 7 - March 20, 2006 - Acquired Matt Thornton from the Mariners for Joe Borchard

In a swap of failed first round picks, its hard to argue with the Sox's results here. Thornton's had his ups and downs, but so far the hard-throwing lefty has been a rock in the bullpen, throwing nearly 40 innings and posting a 2.50 ERA. The change of scenery never helped Borchard, who's bounced around 3 organizations over the past 3 seasons, and is currently playing for the Richmond Braves in AAA, and while he's hitting .274, he's not belting out 29 home runs per season (like he did for the Charlotte Knights in 2005), Williams was able to turn the failed prospect for a reliable lefty out of the bullpen.

#6 - January 15, 2003 - In a three-team trade with the Yankees and Expos, acquired Bartolo Colon and Jorge Nunez for Antonio Osuna, Delvis Lantigua, Rocky Biddle, and Jeff Liefer

This was truly Williams 1st big splash in the trading market. Though he dealt for starting pitchers in the past (David Wells and Todd Ritchie), Colon was the first highly sought after starter that the Sox landed. Though there were plenty of rumors that the Yankees helped pull the deal off to keep Colon from the Red Sox, he ultimately spent 2003 on the South Side. None of the players the Sox gave up ever amounted to much; Biddle spent 2 seasons with the Expos and never pitched more than 80 innings in a season, Leifer bounced around between the Expos, Devil Rays, Brewers, and Indians and is most notable for getting locked in a bathroom during a Spring Training game, Osuna had a nice looking ERA but only pitched about 90 innings in 3 MLB seasons after the trade, and Lantigua apparently never pitched again.

Colon was everything the Sox expected, winning 15 games for a Sox team that should have made the post-season, and while his career in Chicago was short, Colon netted the Sox a pair of compensation picks in the Sandwich Round and 2nd Round of the 2004 Draft from the Angels that turned into Tyler Lumsden and Wes Whisler. Though Colon didn't lead the Sox past September, the excitement and fulfillment of this trade proved that Williams had grown into one of the league's better general managers able to find premium talent and acquire them for scraps, which will be a theme in part 2.

Part 2 (Trades 1-5) in the next few days and then a day or two later, Williams' worst trades.