Chili is just verbalizing the trepidation what we in the DC area have become accustomed to.
I remember years ago, when the Capitals held a two-game lead over Montreal in the playoffs. The local sports talking heads had all but assumed the Capitals would win. However, one of the local sports radio personalities, Steve Czaban, cautioned, "Never underestimate Washington's ability to choke."
The Caps went on to lose that series.
Those of us in the local area aren't bandwagon fans, but we've learned to be a bit cautious in our exuberance.