Someone brought up earlier the reason why I don't really get this move. We're already probably the second best team in the division on paper, and maybe even as good as the Rays, depending on how much you value starting pitching depth and offense (Rays definitely still better in the former, Jays better in the latter). The Orioles most people still view as probably a one-year wonder while the Yankees are older and have their more valuable pieces (Jeter, ARod, Rivera, etc) appearing to be injury prone now as well, and the Sox flat out suck.
Dickey makes us better, but I don't think he's the difference maker in a match up between the Jays and Rays, either over a whole season or in a short series, at least compared to who would likely be getting that start as the roster sits now. Giving up two of the top 30 prospects in all of baseball (and I don't care what anyone says, the fact is that ranking means they're very much more likely to make a big league splash than not) for a player that might make your team ever so slightly better (speaking in terms of talent vs the main competition, Dickey most likely makes the team much better on paper when comparing the rosters with and without him only) over a very short period of time makes no sense to me in this case.
AFAIC, with the roster and prospects we have right now, we should make the playoffs easily at least 3 or 4 times in the next 10 years. Getting Dickey probably means we make the playoffs the next 2, maybe 3 years, but after that we're really building from the ground up again. I'd rather have a constant replenishing of our pro team every few years from prospects than make a short term go at it.
A very good team over 10 years and possibly longer, which when you consider our current prospect depth and AA's ability to draft and find prospects on the sell low list is highly likely, is better than a slightly better team for 3 years and then potentially a team like the one we've had the last 5 years after (unlike what people seem to be thinking here, it takes 3-5 years to build up a good prospect base, and probably another 2-5 after that for said prospects to solidify a pro roster spot), if not at least no guarantee at how good the team will be, is it not?
