For instance "seed" means either to sew 'em or remove 'em. I've often wondered whether your friendly local distributor of "seeded" grapes isn't hoping the potential misunderstanding might get him a slight boost in sales
Stakeholder is one that gets bandied around a lot at my office. Usually it seems to mean anyone who can derail the project, but it's never clear who is a stakeholder and who isn't, although I reckon a stakeholder always adds more work than he contributes. I was amused to find that Wiktionary rates it as a contronym now, since its original meaning was someone who held the stakes of a bet (in escrow) and so in a sense held no interest or control over the outcome - the opposite of what it means now.
I am generally a descriptivist, but when a word has two opposite meanings, I stop using it. The ultimate example is factoid: when coined, it meant something that seems plausible but is not a fact (the suffix -oid denoting looks like but isn't, as in asteroid or android for star-like rock or man-like machine respectively) but nowadays it generally means 'little fact'. So when someone says 'that's a neat little factoid' the statement is utterly ambiguous, though at least the speaker has all their bases covered.