Who Is Chicago's Worst General Manager?

Who Is Chicago's Worst General Manager?

No need to sugar-coat what this piece is all about. Chicago has a wonderful, rich sports tradition and has some of the most exciting young players in every professional sport calling here their home. But, right now, Chicago has some GMs making epic mistakes that will undoubtedly leave some of our favorite teams the laughing stock of their respective leagues.

First of all, just to lay a foundation for this discussion, I'm going to eliminate two Chicago GMs from the field of potential worst: Stan Bowman with the Blackhawks and Gar Forman of the Bulls. While both have experienced success while sitting as GMs of their respective teams, my concern is more that their resume isn't complete enough to evaluate.

While Bowman didn't build the Stanley Cup champions, he hasn't done a bad job in two summers since. However, how much can you really take away from a guy who hasn't been given the chance to bring anyone he's drafted to the NHL, and who has been handed one of the worst salary cap situations in the history of any professional sport? I'm giving Bowman a grade of TBD.

With Forman, the track record so far looks awfully good in many respects. He was named co-Executive of the Year in the NBA last year, and put together a team that landed in the Eastern Conference Finals. He also built a nice team around the league's MVP. But has he done enough in a short amount of time to merit an overwhelming pass, or fail, when grading? Not yet. He's still sitting with a TBD as well.

So the three guys we're talking about are Kenny Williams of the White Sox, Jim Hendry of the Cubs, and Jerry Angelo of the Bears.

Williams, named the GM of the White Sox in November 2000, has the most grace of the three because he's brought a ring to Chicago. But how do you overlook the last couple years on the South Side? He's brought in Manny Ramirez, Alex Rios, Adam Dunn and Jake Peavy, all of whom have been incredible, biblical disappointments. Peavy's injuries have kept him off the mound most of the time he's been a member of the White Sox, while Rios and Dunn have been ghosts. The hardest part of this season's team to stomach is this harsh reality: Williams is spending $24M on two of the worst slugging percentages in major league baseball in Rios and Dunn.

We also cannot ignore the success of former White Sox around baseball. Gio Gonzalez is a 25-year-old All Star this year with Oakland, averaging almost a full strikeout per inning while cutting his ERA to a career-best 2.84 on a bad team. Similarly, Nick Swisher has been pretty good for the Yankees; his 62 RBI are more than Dunn (38) and Rios (23) combined. Aaron Rowand won a subsequent ring in San Francisco, while the Sox haven't replaced him in center yet, while Jim Thome might not be a daily impact player for the Twins but still has managed 27 RBI in only 147 at bats this year.

For his efforts, Williams has the White Sox payroll sitting at an all-time high (nearly $128M) and the team sits three games out in the Central Division and 11 games back of the Yankees in the Wild Card race entering Sunday.

During Williams time as GM of the White Sox (2001-present), they have been in the playoffs twice (2005, 2008).

Hendry's resume is a series of contraditions. He took over as Cubs GM in July of 2002, and the Cubs jumped to a late-inning implosion from the World Series immediately in 2003. But since then the Cubs have been little more than an overwhelming disappointment. This is the fourth consecutive year the Cubs payroll will be over $118M, and the Cubs have three postseason games to show for it. Indeed, in Hendry's time as GM on the North Side, the Cubs have won seven games in three postseason trips (four of which were in the division series against Atlanta in 2003).

This year, while Williams has missed on Rios and Dunn but is at least close enough to the division lead to justify staying put at the trade deadline, Hendry has taken the headless chicken approach to moving players. Only the Houston Astros have a worse record than the Cubs in the entire majors, yet the Cubs have some veterans that would probably be able to bring back decent prospects in a trade with a contender. While Aramis Ramirez and Ryan Dempster have the ability to veto a trade out of Chicago, Carlos Pena and Marlon Byrd could be exceptional additions for a team looking to add a bat for a pennant race.

Yet the Cubs do nothing.

The Cubs suck, and Hendry's lack of vision is a major contributor to that reality. If the Ricketts family doesn't notice the Cubs' record being half-way down the toilet drain, they are certainly seeing all the empty seats at Wrigley Field this year. One seat that should be empty the minute the 2011 season ends should be in the General Manager's office at Wrigley. Hendry's time in Chicago needs to end.

And yet perhaps the most confounding GM in town might be Jerry Angelo.

The draft means more in the NFL than in any other sport, and Angelo has been exceptionally awful at the league's annual selection meeting. Consider the players taken by Angelo in the first round of the NFL Draft while the Bears' GM (not including 2011):

  • 2010: none
  • 2009: none
  • 2008: Chris Williams, OL
  • 2007: Greg Olsen, TE
  • 2006: none
  • 2005: Cedric Benson, RB
  • 2004: Tommie Harris, DT
  • 2003 (14): Michael Haynes, DE
  • 2003 (22): Rex Grossman, QB
  • 2002: Marc Columbo, OL

Columbo and Benson had to go somewhere else to be worth anything in the NFL, and Harris became the poster child for underwhelming after an explosive early career. Grossman was "our quarterback," and Olsen never found a quarterback - or offensive coordinator - that knew how to use his athletic ability. From this list, Williams is the only guy left on the roster.

In Angelo's tenure, the team has won three division championships and played in one Super Bowl. And yet how do you handle winning the division in 2010 over an injured Packers team that eventually won the Super Bowl? Moral victory?

Look at the last two postseasons from Angelo.

He "upgraded" his blocking tight end position (something Mike Martz doesn't use) by giving Brandon Manumaleuna a five-year, $15M contract. He also "upgraded" his short-yardage and back-up running back position by giving Chester Taylor a four-year, $12.5M deal.

This summer, he "upgraded" the tight end position by trading former first round pick Olsen for a third rounder, cutting Manumaluena and signing Matt Spaeth. They then signed former Cowboys running back Marian Barber to a two-year deal, again "upgrading" the running back position.

Meanwhile, popular veterans Olin Kreutz and Brad Maynard are leaving. Kreutz was reportedly willing to take a substantial paycut to stay in Chicago, but the organization allegedly wanted the All-Pro to take another $500k off the top. Disrespectful? Perhaps. Stupid? Absolutely. The team doesn't have a replacement for the only player the organization has called their starting center for the last 12 years, which included six Pro Bowls.

The Lombardi Trophy is sitting a couple hundred miles north of Soldier Field, and the best Angelo can do is... Roy Williams?

It's hard to say who the worst GM in town is, but there are three guys trying really hard to at least win that crown this year.

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