To start, if you're wondering what the Rule Five draft is, you can read this Wikipedia article for a quick explanation. In short, it's a way for players who are stuck in an organization to quickly advance to the major leagues with another team.
If a player is selected, they have to remain in the majors for the entire season. If the team can't keep them there, they are offered back to the original organization. In 2008, the Yankees lost Reegie Corona, Ivan Nova, Zach Kroenke, and Jason Jones in the Rule Five draft.
The Yankees took the first three back, and worked out a deal with the Twins to let them retain Jason Jones. There are three players eligible for the Rule Five draft who are locks to be added to the 40 man roster. I believe that the deadline for them to be added is Nov. 20, and the actual Rule Five draft will take place on Dec. 10. Austin Jackson, Ivan Nova, and Kevin Russo will all be added to the roster.
They are all players who have had success at AAA, meaning it wouldn't be too difficult for another team to hold them on their roster all season. These guys all have futures with the Yankees, so they need to be retained.
After adding those three, I believe that the Yankees will have room to protect two more players. The notable guys to look out for are pitchers Grant Duff, Romulo Sanchez, Kanekoa Texeira, Zach Kroenke, Kevin Whelan, George Kontos, and position players Reegie Corona, Eduardo Nunez, and Colin Curtis.
Romulo Sanchez put together a very nice season for the Yankees, and I ranked him as the 27th best prospect in the Yankee organization. He was hitting 98-99 as a starter, while getting a ton of ground balls and a strikeout per inning.
He'll be 26 in 2009, a bit old for a prospect, but an arm like that is worth keeping around. After the top three guys, Romulo is my first choice to be protected. The X-factor here is that Romulo is a fun name to say, giving him an extra edge.
Grant Duff is another guy who is a bit older, and also has a huge fastball. He pitched well in AA and has been pitching pretty well in the Arizona Fall League. I'm not too high on him, but he is a guy who would almost definitely be snatched away in the Rule Five. With his fastball, he could stick as the last guy out of the bullpen for another team.
Kanekoa Texeira was thrown into the Swisher deal and was effective and versatile for Trenton in 2009. He throws a heavy fastball that generates ground balls and he doesn't walk too many batters. He is definitely a risk to be taken and warrants protection.
Zach Kroenke is a lefty with fringy stuff who put up a low ERA for Scranton in 2009. With Phil Coke, Mike Dunn, and Damaso Marte fighting for appearances in 2010, I don't see room for a guy like Kroenke on the 40-man.
Kevin Whelan has always tantalized with his stuff, but his control issues are severe. These problems didn't go away in 2009, as he walked 5.5 batters per nine innings. If another team takes him, it's hard to see him sticking in the majors with control issues like that.
I don't see the Yankees protecting George Kontos, as he is out with Tommy John Surgery, but he could definitely be taken in the draft. He was next in line for a call-up to the majors before succumbing to injury. If another team takes him, they can stash him on the DL, give him some time to rehab and then have to keep him on the major league roster for a year. Before his injury, he was basically big league ready, so a team would be smart to grab him from the Yankees for nothing.
The position player who is garnering the most support to be protected is Eduardo Nunez. I have frequently voiced my thoughts that he is overrated, but others still really like the guy. The reason I don't think he needs to be protected is because I don't see any way he can stick with a major league team. He hit well in AA, but his bat is nowhere near major league ready.
The more glaring reason is his defense. He has a strong arm, but is a pretty bad defensive shortstop at this point. If another team drafted him and kept him, they would pretty much be playing with a 24-man roster all season long, so it is very doubtful he needs to be protected.
Colin Curtis and Reegie Corona don't really do anything to stick out. They play solid defense, but don't possess much power and don't project to be regulars. They are both guys who could be taken and stick as bench players, but it wouldn't be much of a loss for the Yankees.
This leaves two spots for Romulo Sanchez, Grant Duff, and Kanekoa Texeira. I would make sure to protect Romulo, because he could help the team in 2010. If the Yankees do in fact have room for another player, I would add Texeira. He has had more success than Duff at a younger age and is more versatile.
Cashman said these things tend to work themselves out, so I wouldn't be too concerned about the Rule Five Draft. If the Yankees let someone get a way, they likely don't believe he is a future regular for them. The depth of the system ensures that the Yankees will lose a few players, and when that happens, be happy for the player who is getting a chance to stick in the majors; don't be upset that the Yankees are losing them.