Top 10 Biggest Chicago Sports Disappointments Since 2000

By Danny Sheridan

With SportsCenter coming to Chicago last weekend to do “TitleTown USA”, it got me wondering how Chicago even qualified as one of the 20 cities. Since 2000, other than the White Sox World Championship, we haven’t had much to get excited about. There have been quite a few disappointments though, and here’s my top 10. These can be individual games, specific teams, front office moves etc. Somehow, the Ben Wallace signing and Jay Williams motorcycle accident failed to make this list.

10. Drafting Cedric Benson

True, the 2005 draft as a whole has been very disappointing thus far, but here’s a list of players selected after the Bears took Benson with the fourth overall pick; Shawne Merriman, Demarcus Ware, Carnell Williams, Frank Gore, Derrick Johnson, Jamal Brown and Logan Mankins. Blame Jerry Angelo if you want, however, remember that a lot of Bears fans wanted Mike Williams from USC, who turned out to be an even bigger bust. Considering Benson recently posed for half as many mug shots as he scored touchdowns last season (yes I made that up myself), letting him go was an easy call.

9. Michael Jordan returning to play basketball

Jordan’s stats (21.5 points, six rebounds, four assists) in his two seasons with the Wizards are deceiving. While Luol Deng would kill for those kinds of numbers, Jordan basically held the franchise back for those two years. It’s possible Jordan came back because he thought teaming with Kwame Brown, Christian Laettner, Tyron Lue and company would bring him yet another title (I’m kidding of course). Whatever the reason, it was a huge mistake. You couldn’t have scripted a better way to go out, with Jordan holding the pose on his game winning jumper against Utah in the 98 Finals.

8. The 2001 NBA Draft

What was Jerry Krause thinking? A guy averages 20 points and 10 rebounds his first two years in the league, and then you trade him for a kid straight out of high school? Mistake number two was picking a guy who couldn’t even dominate against a short group of suburban kids from Schaumburg in the state title game his senior year at Thornwood. How good would someone like Elton Brand look right now on the Bulls? Tyson Chandler failed to average double figure points or rebounds in any of his five seasons with the Bulls, while Eddy Curry’s occasional scoring outbursts were tempered by his laziness and defensive limitations. About the only good thing to come from all this was getting two high lottery picks from the Knicks in exchange for Curry.

7. The 2004 Cubs

Once the Cubs added Nomar at the trade deadline, they became a virtual lock for the postseason and even strong favorites to win the World Series. With a stacked lineup that included huge years from Moises Alou, Derrick Lee, and Aramis Ramirez, plus three aces in Kerry Wood, Mark Prior and Carlos Zambrano, this Cubs team was loaded. They won 88 games solely based on talent, choking it away in the final week by losing seven of their final eight games. Thank Latroy Hawkins for blowing three games during that stretch. Plus, the Cubs uninspired play ended up costing Steve Stone and Chip Carey their jobs.

6. Bulls not trading for Kobe

I’m still waiting to hear a decent explanation from John Paxson for this decision. Oh wait, now I remember; Luol Deng, Ben Gordon, and Tyrus Thomas were all going to be future all-stars. Meanwhile the Bulls lost a chance to acquire the best player on the planet. Kobe wanted to come to Chicago and the Bulls had the young players to make the deal work. Forget for a second how Kobe played in the Finals. Put him on the Bulls, and they become one of the East’s better teams. Now, they’re stuck with a bunch of spoiled, underachieving, selfish players who haven’t accomplished a thing yet in this league. Sure hope Derrick Rose is the real deal.

5. Cubs getting swept by Diamondbacks

On paper, it looked like the perfect match up. Arizona had a young, unproven lineup, and really only one pitcher in Brandon Webb who was any good. The Cubs were streaking, had the experience, and the statistical advantage at every position except center field. Getting shut down by Webb is one thing. Letting Augie Ojeda, Stephan Drew, and Doug Davis look like world beaters is another. The best two hitters, Ramirez and Soriano, hit .000 and .143 respectively, and the Cubs led for only one half inning the entire series. By the way, Lou Piniella made the correct call in taking Carlos Zambrano out after six innings in game number one.

4. Injuries to Mark Prior and Kerry Wood

If both those guys had stayed healthy, I’m guaranteeing the Cubs would have at least one or two World Series by now. We saw what happened when they stayed off the D.L. in 2003, but that was a rare occurrence. Prior has won one game since 2005, while Wood is now making Cubs fans extremely nervous every time he takes the mound in the ninth inning. People point to Dusty Baker overusing Prior in 2003, when he averaged 114 pitches per start. What’s ironic is that when Prior first came up, his mechanics impressed all the scouts. Years later, his mechanics are probably what ended up costing him his career.

3. Illinois losing to North Carolina

I wanted to put this at number one, considering how much I followed and enjoyed watching this Illinois team all season. Whether it was Dee Brown giving the school some great pub with his jersey popping, Luther Head draining three’s, Deron Williams running the show, or Bruce Weber sporting that classic look of disbelief on his face over an official’s call, this team came within a few breaks of going 39-0. Carolina had four guys who ended up being lottery picks in that year’s draft, and Illinois played poorly that night. Still, despite trailing virtually the entire way, the game was tied with one minute left. That’s with Illinois shooting 38% and attempting 40 three pointers, compared to Carolina’s 51% shooting. Plus, the officials let Sean May get away with murder.

2. Bears losing Super Bowl

In all honesty, the Colts were simply better. The talent gap between the two quarterbacks was too much to overcome. The fact that it was pouring certainly didn’t help the Bears either once they got behind. Anytime you lose the Super Bowl, it sucks, but at least the Bears didn’t lose on some fluke play or in heartbreaking fashion. It’s funny how one play can alter a football game. With the Bears trailing only 16-14 and driving, Grossman threw an ill advised pass that Kelvin Hayden returned for a score, basically sealing the deal. At least we’ll always have Devin Hester’s opening kickoff return to remember.

1. Cubs losing 2003 NLCS

Fox showed the Marlins on the bench at the start of the eighth inning in game six, all sitting quietly with their heads down. Even they knew it was over. Unfortunately, someone forgot to tell that to Mark Prior, Alex Gonzalez, Dusty Baker, and of course Steve Bartman. Yes, Alou would have caught that foul ball, but that’s not what cost the Cubs this series. Prior hanging pitches, Gonzalez botching a double play, Baker’s indecision, and Kerry Wood’s game seven performance all played bigger roles in this meltdown. I hate it when people argue how good that Marlins team was. The Cubs were clearly better, and would have beaten the Yankees in the World Series.