You could switch "So Cub" with "So Cleveland" and it would be totally believable. Like this:
The last two times the Indians went to the World Series, they didn’t just lose, but they lost in seven games, and not just in seven games, but in extra innings.
In 1997, the Marlins beat the Indians in 11 innings, and of course the Cubs just beat them in 10.
If you want to put a face on that heartbreak -- besides that racist Chief Wahoo, I mean -- try Sandy Alomar Jr.