River Brian, in the first round I take a long term can't miss young player to build and market my team around for many years. With Kershaw, Trout and Harper being 24, 20 and 19 respectively, if you sign them long term they could be playing at a high level effectively for 15-20 years for the franchise. As far as the later rounds are concerned, from your examples I would take A-Gon over Rizzo, McCann over Grandal, and Bauer over Halladay. Yeah, youth might play a part of it after the first round, but you fill your roster out to make the best team you can. After you get your "build around him player", you can start adding in the blue hairs and such and take the best available player to work towards being a World Series Victor!