The front office will undoubtedly be faced with many tough decisions this winter. We've discussed many of them; Crawford, the catcher situation, whether or not to trade Bartlett, etc. One decision that won't be so tough is deciding which players to put on the 40 man roster, the deadline for which is Friday.
Currently the Rays have three open spots on their 40 man roster, with another one possible since Jeff Bennett is not likely to remain with the team. There's no question that two of the roster spots will go to Desmond Jennings and Jeremy Hellickson, two of the top prospects in the organization, and baseball in general. As RJ noted a couple of months ago, the third spot will probably go to Aneury Rodriguez, the young reliever the Rays received in the Jason Hammel trade. The remaining roster spot, assuming Jeff Bennett isn't still around, will likely remain open to leave room for any player the team selects in the Rule 5 draft.
The organization has done many things right over the last few seasons, but Rule 5 draft has been one they have yet to figure out, though in their defense not many teams do. Here is a list of the Rays Rule 5 draft picks since 2006:
2006: Ryan Goleski
Goleski was selected first overall by the Rays, but would not stick around long and was sent back to Cleveland. After a .249/.333/.429 season in 2008 he would be out of baseball at 26 years old. The 2006 draft was the one that saw Josh Hamilton be claimed by the Reds after being left unprotected by the Rays. Also, Joakim Soria was selected second overall. He's ended up doing pretty well for himself.
2007: Tim Lehay
Once again the Rays would have the first selection, this time taking Tim Lahey. The 6'4 inch right hander would be a quick out; The Rays sold him to the Twins for cash considerations. No other players of note were taken in 2007.
2008: Derek Rodriguez
Upon the success of the 2008 season the Rays were finally not awarded the first pick. Instead they selected 19th and chose reliever Derek Rodriguez from the White Sox. Rodriguez would struggle in the spring and would be sold back to the White Sox for $25k. In this draft the Rays would unexpectedly lose reliever Eduardo Morlan, who they had acquired along with Matt Garza and Jason Bartlett in the Delmon Young trade, to the Brewers. However, Morlan would not make the Brewers roster and was sold back to the Rays for $25k, offsetting the cost of the Rodriguez deal.
As you can see, the Rule 5 draft has not been a very fruitful endeavor for the Rays in recent seasons, but that's ok. Getting lucky enough to draft a Johan Santana or Joakim Soria is fine and dandy , but protecting immense talents like Jennings and Hellickson far out weighs any player the Rays may select.