Knowledge, Lotteries, and the Future

I often hear people concede skepticism about the future quite easily when pressed to defend a principle about knowledge. A recent example is Dretske in response to John Hawthorne in the Contemporary Debates book. John presses him on an example having to do with a future event and Dretske response blithely "I'm a bit of a skeptic about the future" (p. 44). I've seen it in print a couple of times and I hear it fairly often in discussions with epistemologists. I say I'm going to Italy next summer. You challenge this, and I respond "Very well, I'm planning on going to Italy." Sounds good right? I want to explore that a bit.