You clearly hate Boston and would want them as far away as possible, so I clearly cant choose the cup in front of me.

Man in Black: All right. Who do you root for in tonight’s match up between the Red Sox and the Rays? The battle of wits has begun. It ends when you decide and we find out who is right… and who is out of the playoffs.
Vizzini: But it’s so simple.  All I have to do is divine from what I know of you: are you the sort of man who would want to battle a new enemy or an old and battered enemy?  Now, a clever man would want to keep as many enemys as far away as possible, because he would know that only a great fool would want both his enemys at arms reach. I am not a great fool, so I can clearly not choose the Red Sox.  But you must have known I was not a great fool, you would have counted on it, so I can clearly not choose the Rays.
Man in Black: You’ve made your decision then?
Vizzini: Not remotely. Because the Red Sox come from Boston, as everyone knows, and Boston is entirely peopled named Mac and Sully, and those people can be murderous when it comes to playing at Fenway, so I can clearly not choose the Red Sox. 
Man in Black: Truly, you have a dizzying intellect.
Vizzini: Wait til I get going! Now, where was I?
Man in Black: Boston.
Vizzini: Yes, Boston. And you must have suspected I would have known the Red Sox origin, so I can clearly not choose the Rays. 
Man in Black: You’re just stalling now.
Vizzini: You’d like to think that, wouldn’t you? You’ve beaten my giant, which means you’re exceptionally strong, so you could assume that you can take your chances against both Boston and Tampa, trusting on your strength to save you, so I can clearly not choose the Boston.   But, you’ve also bested my Spaniard, which means you must have studied, and in studying you must have learned that no lead is safe, so you would want your closest enemy to fall further behind, so I can clearly not choose the Rays. 
Man in Black: You’re trying to trick me into giving away something. It won’t work.
Vizzini: IT HAS WORKED! YOU’VE GIVEN EVERYTHING AWAY! I KNOW WHICH TEAM TO ROOT FOR!!
Man in Black: Then make your choice.
Vizzini: I will, and I choose – What in the world can that be?
Vizzini: [Vizzini gestures up at the Scoreborad.  The Man in Black looks. Vizzini looks at the playoff-odds report from baseballprospectus.com]
Man in Black: What? Where? I don’t see anything.
Vizzini: Well, I- I could have sworn I saw something. No matter. First, let’s choose, I’ll take Boston; You take Tampa.
Man in Black: You guessed wrong.
Vizzini: You only think I guessed wrong! That’s what’s so funny! I checked the stats while your back was turned! Ha ha! You fool! You fell victim to one of the classic blunders – The most famous of which is “never get involved in a land war in Asia” – but only slightly less well-known is this: “Never go against Veteran Pitching when the Playoffs are on the line”! Ha ha ha ha ha ha ha! Ha ha ha ha ha ha ha! Ha ha ha…
Vizzini: [Vizzini stops suddenly,his smile frozen on his face and falls dead]
Buttercup: And to think, all that time the right choice was Tampa.
Man in Black:  There is no right choice.  Regardless of who wins, if the Yankees win their games, they come out of the weekend with a better chance of making the playoffs.