Theres' so much that has to happen for that to work.
A lot of people view Hamilton as a utility infielder/speedbench bat, Medidroth is a middling prospect with minor league production but serious questions about having the ability to impact the baseball at the MLB level.
That's not worthless, but just think if you were getting those two guys in return what you'd be willing to give up?
Now, said team has to believe in the upside of those guys, and have an extra 40 man spot available to carry an extra guy who will have to be carried on a 40 man.
The odds of those stars aligning are slim.
Hypothetically Hamilton + Yorke gets you Tristan Casas. I would never make that trade.
Now, if we are talking about a rental, that's a different story, but I wonder if a prospect that offers the flexibility of not needing to be added to the 40 man this offseason as being more valuable to a team. POSSIBLY, again stars must always align.
For example. I think Hamilton/Romero might actually be more enticing, yes Romero isn't ranked as high but a team has the luxury of being able to keep him off the 40 man, develop him and see if he can become what comes along with a first round draft pick shine.