With the baseball season quickly approaching, and being a continuously disappointed Cubs fan year in year out, I felt it necessary to talk about the top 6 disappointments I have experienced. I know, it seems that every year has some kind of major disappointment with the Cubs, but I will be the first to admit that some years I fully expect them to be crappy. Needless to say, those years probably won't make this list. This list will only feature events that have happened in my lifetime. As much of a disappointment 1969 was, I cannot put that on here because I didn't experience it.
6. 1998: Kerry Wood was a rookie in 1998 and was coming off a Rookie of the Year win and, in my opinion, the greatest pitched game I have ever seen 
when he struck out 20, walked none, and gave only 1 hit. But the playoffs were a different story. The Cubs had to beat the Giants on a play-in game just to be the wild card that year. They wound up drawing the Atlanta Braves that year and faced, in order, John Smoltz, Tom Glavine, and Greg Maddux in the the playoffs. In hindsight, this doesn't sound like too much of a disappointment. Actually, during the regular season the Cubs had a winning record against the Braves and my opinion at the time, a better team. Needless to say, the Braves swept the Cubs in 3 games with only one of them being remotely close.
when he struck out 20, walked none, and gave only 1 hit. But the playoffs were a different story. The Cubs had to beat the Giants on a play-in game just to be the wild card that year. They wound up drawing the Atlanta Braves that year and faced, in order, John Smoltz, Tom Glavine, and Greg Maddux in the the playoffs. In hindsight, this doesn't sound like too much of a disappointment. Actually, during the regular season the Cubs had a winning record against the Braves and my opinion at the time, a better team. Needless to say, the Braves swept the Cubs in 3 games with only one of them being remotely close. 5. 1989: In 1989, the Cubs had a great duo of rookies in Jerome Walton and Dwight Smith, who finished first and second in the Rookie of the Year voting, respectively. If you couple this with Ryne Sandberg, Andre Dawson, Greg Maddux, and Mark Grace, you had the makings of a really big season. They seemed to breeze through the season only to meet the San Fransisco Giants in the playoffs. They probably would have been OK if anyone other than Will Clark was playing first base for the G-men. He batted .650 with 2 HR's and 8 RBI in the series and completely took the wind of the sails for the Cubs.
4. 2007: This was a strange matchup because the Cubs SHOULD have played the Phillies since they were both division winners and the D-backs SHOULD have played the Rockies since that would have been a 1-seed against the wild card. But since divisional teams can't meet in the first round, the Cubs had to play the D-backs. The Cubs had an OK team this year and I really didn't expect them to make the playoffs but they got really hot at the end of the year and headed to the playoffs with a lot of momentum. But the lack of offense from the Cubs finally caught up to them and they got completely shut down by the D-backs. The only positive from this series was that Geovany Soto used this as his coming out party and it propelled him to a Rookie of the Year campaign the following year.
3. 2008: Here are where the fun ones begin. 2008 was a year that marked a century since the Cubs last won a world series. That's right, 100 years! So coming off of a good campaign in '07, everyone thought the Cubs would finally get that title. Almost for the entire season, the Cubs had the best record in the major leagues. They won 97 games and had all of the cylinders hitting for the entire season. The starting pitching was great, the bullpen was lights out, the lineup was extremely productive. But just as they did in '07, they completely pissed down their legs in the playoffs. Watching them in the regular season was a complete joy. Conversely, I could not bear to watch them in the playoffs because they could barely hit the ball out of the infield. The Cubs had only one less hit in the series than the Dodgers but had FOURTEEN (14) fewer runs. Let me say that again, one less hit and FOURTEEN fewer runs. Talk about a complete lack of focus. This series made me so extremely disappointed that I swore I would not watch them in the playoffs until they actually win a playoff game. Now we all know that's a lie but that's what I felt.
2. 1984: Before the ball rolled through Bill Buckner's legs for th
e Red Sox, Leon Durham thought that actually catching a softly hit ground ball with runners on base would have been right thing to do. Unfortunately, his body did the opposite and he did not catch the ball and the Padres wound up winning the game and the series. The Cubs were up 2-0 in a best of 5 series only to lose three straight (that happens frequently with them). They had a great team of Sandberg, Jody Davis, Ron Cey, Gary Matthews, Rick Sutcliffe, Bob Dernier, and Lee Smith. They simply should have won this series. I will give great credit to Steve Garvey for batting .400 and knocking in 7 RBI. But the Cubs collapsed big time on this one. At the time, they hadn't been to the playoffs in over 40 years. This should have been the one and it wasn't. F'n Leon Durham!
e Red Sox, Leon Durham thought that actually catching a softly hit ground ball with runners on base would have been right thing to do. Unfortunately, his body did the opposite and he did not catch the ball and the Padres wound up winning the game and the series. The Cubs were up 2-0 in a best of 5 series only to lose three straight (that happens frequently with them). They had a great team of Sandberg, Jody Davis, Ron Cey, Gary Matthews, Rick Sutcliffe, Bob Dernier, and Lee Smith. They simply should have won this series. I will give great credit to Steve Garvey for batting .400 and knocking in 7 RBI. But the Cubs collapsed big time on this one. At the time, they hadn't been to the playoffs in over 40 years. This should have been the one and it wasn't. F'n Leon Durham!1. 2003: Here we go...5 outs away, Prior on the hill, Cubs in the lead...then it happened. I'm not going to say that Steve Bartman cost the Cubs the game because any fan would
have attempted to catch that foul ball. But the fact that happened causing Alou not to catch the ball which gave the Marlins another chance completely shifted the landscape of that game. The very next batter hit a (very) soft ground ball to shortstop Alex Gonzalez, who during the regular season committed only 9 errors. Just as Leon Durham did 19 years before, Gonzo booted the ball and allowed the go-ahead run to come in and score. The next night Kerry Wood was pitching and one could just feel that things weren't right. Forget the fact that Wood and Prior hadn't lost back to back games all year. Something just didn't sit right that night and you could just feel that every time the Cubs did something positive, like Wood hitting a HR, the Marlins would counter. Sure enough, the Marlins won the decisive game 7 in Wrigley and danced their way to a series title over the Yankees. Did I mention that the Cubs had a 3-0 lead in the best of 7 series and wound up losing 4 straight? I told you it was a common theme. Words cannot begin to describe the disappointment I felt after both games 6 and 7. I'd like to think that as a somewhat intelligent adult, I wouldn't get too caught up in the emotional impact of a loss, but 2003 was painful. 5 outs...
have attempted to catch that foul ball. But the fact that happened causing Alou not to catch the ball which gave the Marlins another chance completely shifted the landscape of that game. The very next batter hit a (very) soft ground ball to shortstop Alex Gonzalez, who during the regular season committed only 9 errors. Just as Leon Durham did 19 years before, Gonzo booted the ball and allowed the go-ahead run to come in and score. The next night Kerry Wood was pitching and one could just feel that things weren't right. Forget the fact that Wood and Prior hadn't lost back to back games all year. Something just didn't sit right that night and you could just feel that every time the Cubs did something positive, like Wood hitting a HR, the Marlins would counter. Sure enough, the Marlins won the decisive game 7 in Wrigley and danced their way to a series title over the Yankees. Did I mention that the Cubs had a 3-0 lead in the best of 7 series and wound up losing 4 straight? I told you it was a common theme. Words cannot begin to describe the disappointment I felt after both games 6 and 7. I'd like to think that as a somewhat intelligent adult, I wouldn't get too caught up in the emotional impact of a loss, but 2003 was painful. 5 outs... 
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