Think of it this way. If you want to learn what constitutes strong chess play, will you learn best from playing a) yourself or b) a much stronger player?
Having a "collaborative" exchange with a chatbot is of the same strength as playing chess with yourself, for the purposes of investigating what "thinking" consists of.
The Turing Test is useful precisely when we are trying to "break the bot" as you put it; in fact, when the bot is pitted against a real human, who in that contest plays the role of the chess master.
Saying that Eugene Goostman "passed the Turing Test" is like crowning me World Chess Champion, based on the amazing record of beating 70% of a random sample of six year olds.
> "if you ran into this robot in real life
You wouldn't ever "run into" Eugene Goostman in real life, because it lacks the kind of generalist problem solving ability that would allow it to insert itself into any "real life" situation - an ability that even six year olds possess. It literally couldn't even get out the gate.