Take a good look at the screenshot below (click for a full-size version):
My 7-year old son and I were playing chess on the computer. He's white, I'm black (um...the pieces, that is).
I've had games end in draws before, but only when each player is down to their King (which = automatic draw).
It took a moment for me to realize what happened here: On my last move, I moved my Queen to A4 to take out one of his pieces. Look carefully and you'll see that the black white King is NOT in Check at the moment...but can't move anywhere without going into Check.
Thus, even though he's NOT in Check, the game is over...as a draw.
Even though I had my Queen, both Rooks, a Bishop, a Knight and several pawns left...while he only had his King.
That's right. Nine to 1 advantage and I still couldn't actually "win" due to the bizarre rules of the game.
The filibuster metaphor just writes itself, although a better parallel might be the "secret holds" that seem to pop up in the Senate from time to time.
Update: Fixed a typo above. Also, just to clarify: Yes, I let him win once in awhile (about 1 game in 5). I don't want him to become discouraged or bitter, but I also want him to learn to be a good sport and to develop his strategic skills.
In this case, it was kind of a weird fluke (note that he couldn't put himself into that position, only I could).
Update x2: Now he's teaching my mother-in-law how to play.