The Rule 5 draft is one of the odd events in baseball, a chance for rebuilding teams to steal a talented gamble from a prospect rich team. You have to keep a draftee on the 25 man roster for the entire season, or offer to sell him back to his original club (as happened to Reegie Corona last season).
It's a testament to the job Cashman has done rebuilding the franchise that the Yankees lost 6 players in the Rule 5 last season, including 5 pitchers, and still had the arms to play an effective musical chairs in the bullpen.
Chad Jennings breaks down the (relatively) high profile Rule 5 eligible players:
Pitchers: J.B. Cox, Grant Duff, Alan Horne, Zack Kroenke, Ivan Nova, Jonathan Ortiz, Romulo Sanchez, Josh Schmidt, Brett Smith, Kevin Whelan, Eric Wordekemper, Jonathan Hovis, George Kontos, Paul Patterson, Kanekoa Texeira
Catchers: Kyle Anson, P.J. Pilittere
Infielders: Reegie Corona, Chris Malec, Mitch Hilligoss, Eduardo Nunez, Luis Nunez, Kevin Russo, Kevin Smith
Outfielders: James Cooper, Colin Curtis, Seth Fortenberry, Austin Jackson
The no doubters are AJax (OF), Luis Nunez (SS), Kevin Russo (2B) and Kanekoa Texeira (the pitcher thrown into the Swisher deal to prove Cashman's brilliance).
Like Chad, I think the Yanks need to protect Sanchez, Nova, Horne, and Whelan, all of whom still have big upsides. I'm indifferent to the position players except Reegie Corona, but there are probably too many middle infielders on the 40 man already.
I also think protecting Colin Curtis is worth while. He is raking as a LF in the Arizona Fall League (which is a hitters' league, so don't get too excited), and I think that exposure will move him up the board of some teams.
Remember that you don't want to fill the 40-man, because then you have to pass your prospects through waivers when you sign free agents like Pettitte, Matsui or Damon.
Who would you protect and how?