What happened to the Cubs this season? Guest author Melissa Rakestraw takes us from heady summer days to autumn nights chilly with defeat, and, as a bonus, ranks the three worst heartbreaks in recent Cubbies history.

The 2008 Chicago Cubs, 97-64, NL Central Division Champs. It was not much of a surprise to me to see this team win the division. I certainly did expect them to win their division; but that doesn’t mean I didn’t appreciate the manner in which they were able to do it. There is no question that this season was the best summer of baseball I have seen a Cubs team produce. They entertained their fans, winning more home games than any other team in the NL, and looked good doing it. There were many great games and moments in those games I won’t forget.

Opening day at Wrigley Field, the Cubs main off-season acquisition, Kosuke Fukudome, hit a 3-run homer in the bottom of the ninth off of the Brewers’ Eric Gagne to tie the game and send it to extra innings. It didn’t end in a Cubs victory that day, but it was an impressive debut for the Japanese rookie and a moment that I was able to witness first hand.

Jim Edmonds, the former Cardinal, winning over the hearts of Cubs fans on June 12 with a game-tying homer in the bottom of the ninth against Atlanta, to send the game to extras, leading to an eventual Cubs’ win. Aramis Ramirez with a walk-off solo home run against the White Sox to give the Cubs a 3-2 win. The Cubs scoring 8 runs in one inning against those same White Sox, with Jimmy Ballgame providing 2 home runs in that outburst. The Cubs coming back from a 9-1 deficit to beat the Colorado Rockies at Wrigley. The Cubs’ 4-game sweep of the Brewers at the end of July up in Milwaukee, effectively sealing their fate as division champs.

Ted Lilly running through Cardinals catcher Yadier Molina at home plate attempting to score at Busch Stadium. He was out, but his effort seemed to symbolize the Cubs’ resolve to not let anyone or anything stand in their way.

The Cubs won that game as well. Geovany Soto, the rookie catcher, hitting a 3-run homer in the bottom of the 9th against the Brewers. The Crew had led 6-2 entering that inning and the Cubs went on to eventually win that game in extras as well. September 20, Wrigley Field, the Cubs beat the Cardinals to clinch the NL Central. Cubs players returned to the field after the final out and celebrated with the fans singing the chorus to “Go Cubs Go.” It was the first time since 1908 that the Cubs had won back-to-back division titles. Lastly, I won’t forget Carlos Zambrano’s no-hitter, thrown against the Houston Astros in the Brewers’ Miller Park. It was a dominating performance by Big Z and the first no-hitter thrown by a Cub since Milt Pappas in 1972.

These are just some of the best memories that I have from a season filled with great moments. There is no way that 3 games in October will erase them. Those were the games that made fans fall in love with this team. Of course, when you fall in love with someone or something, you always set yourself up for possible heartbreak — and unfortunately, this season ended in more heartbreak for Cubs fans.
I will admit that at the start of the season I didn’t think the Cubs were headed for the World Series, but after witnessing such a great performance all season long I thought they had a legitimate shot at getting there — and maybe even winning it all.

With Zambrano, the acquisition of Rich Harden, and the incredible 17-win season of Ryan Dempster, I thought the Cubs had fortified the top of their rotation and put themselves in a position to win the NL pennant and beyond. I do believe the post-season is a crapshoot and I know the best team doesn’t always win a 5- or 7-game series, but I liked my guys’ chances going in. And I’ll admit that with the playoffs approaching, I started to look at things more from an emotional standpoint, wanting my team to take it all as opposed to looking at it with a logical perspective. Yet if you had told me that the Dodgers would sweep the Cubs, I would not have been shocked. Although I didn’t think it probable, I was aware it was possible. I was not shocked by the fact the Cubs were defeated, but rather the way in which they were defeated. I couldn’t help but feel disappointed by the Cubs’ sub-standard performance.

Not to take anything away from the Dodgers, but the Cubs didn’t seem to make it very difficult for them. That caught me off-guard. I watched this team battle all summer long — they were consistent throughout. When Ryan Dempster walked 7 batters in game 1, more than he had walked in any appearance all season, I was surprised. Demp was 14-3 at Wrigley this season and I thought he would give his team a chance to win. In the 5th inning, he walked 3, and with 2 out and an 0-2 count on James Loney, he gave up a grand slam. It only put the team in a 4-2 hole, but was a blow they didn’t recover from in a game that ended 7-2.

But as improbable as Dempster’s performance was in Game 1 it paled in comparison to the events that would unfold in Game 2.
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I really loved Nomar. Or, as we in Boston call him, Nomah. Or even as I sometimes call him in my dreams, Nomie. I do secretly suspect him of juicing (that SI cover bears no resemblence to the skinny prospect I first adored, and the man’s body today is basically held together with duct tape and silly putty where the connective tissue used to be). But still, I love. I love his hustle. I love his friendship with the late Ted Williams. I love that he’s married to Mia Hamm.

Then there’s Manny. While my love for Nomar was pure and trusting, my love for Manny is sick and twisted. I need him more than I like him. Why? Because without his bat—or an equivalent—protecting David Ortiz, in the words of Papi himself, “I won’t see a pitch. I wouldn’t even pitch to myself.” And while Manny—who’ll dive headfirst into a base but rarely attempts a diving catch—won’t make anyone’s list of top defensive outfielders, he does return the ball quickly from Fenway’s quirky left, barehanding the ball or transferring it from glove to hand with an infielder’s dexterity. Look, I know that he’s just not that into me, and yet I can’t let go. When Manny missed the All-Star game again this year, I excused it because I thought a) maybe he’s really hurt (yes it’s pathetic, the way we lie to ourselves) and b) so he’s skipping out on a meaningless exhibition game–he would never do that to me. Ha! Well hell hath no fury like a Sox fan scorned.

So I just have to say it: Manny, you asshole, Nomar WOULD NEVER HAVE DONE THIS TO ME! Behold Manny Ramirez, spending the stretch hitting the showers, making cryptic comments, asking for a trade and getting clean MRIs done on his knee. So much for 2004’s World Series MVP.

Meanwhile, The One That Got Away is playing hurt and hit two walkoff homers in the space of a week to keep his team in contention. The first one? Completely crazy. The second? A grand slam! Almost as if to say, “So what if I can barely hobble around the bases? If I hit it out of the park, I can limp around as slowly and painfully as I want! Take that, haters!” Can’t walk? Hit a walkoff!

Oh, Nomie. Whatever happened to us?

And you, Manuel. Next year, you can quit on somebody else’s team and somebody’s else nickel. We’re through. For good!