Changing front-offices isn't going to all of a sudden allow us to throw nearly $100 million dollars on a player who has never even stepped foot into an MLB stadium. If you haven't noticed by now; ownership dictates success. All these teams that are signing these Cuban transfers are owned by financiers that dont mind spending hundreds of millions of dollars to build a winner (Cubs, Dodgers, Red Sox, etc). You think AA wouldn't like to throw a pile of money at a guy? The problem is that Rogers sees this team as a money-making operation first and foremost, therefore when they choose to open the pocket books they want to do it by acquiring players that they know are at least proven on some level. Marketability also plays into effect, as its a hell of a lot easier to shoot commercials and sell merchandise of a guy like Dickey who just won a Cy Young than it is to do the same with some Cuban dude that the general general public has never even heard of.
The power of a "General Manager" is a lot smaller than most of you want to imagine. Look at Loria who basically runs the Marlins, or Steinbrenner with the Yankees. Those guys are/were very open so its easy to see their impact, but a company like Rogers still operates the club in their own way just like those two.