DeRosa cashes in on career year, to sign with Cubs
Corny Bill Simmons-style analogy: The Cubs are kind of like that dorky, slightly clueless guy who tries really hard to keep up with fashion, but no matter what he does, he always seems to be a trend behind the people in the know. He goes to the designer stores and checks out the clearance racks, and something always catches his eye. But he always second-guesses himself. He thinks, "This looks really cool to me, but I'm unsure because it's marked down so much." After fretting about it for a few minutes and trying it on a few times, he decides to buy it. Later on when people see him wearing it, they either snicker a little at his charming but vain efforts if they're a fashion buff, or they simply don't notice. In the end, no one really cares or notices much, and he's squandered a small sum of money that could've been saved for the transmission leak on his car.
And for the hell of it, let's call this slightly clueless guy Mike Sever.