The Pirates have approached Nate McLouth, Paul Maholm and Ryan Doumit about extensions, the Post-Gazette reports.
The Bucs signed three players in similar situations (Matt Capps, Freddy Sanchez and Ian Snell) to extensions last Spring, and two of those players were a complete mess in 2008. But the terms of these kinds of contracts for pre-arbitration players are so favorable that the Pirates really need to keep taking chances with them. Snell's contract, in particular, is great--yes, he was terrible in 2008, but the Pirates are only on the hook for $7.25 million in 2009 and 2010 combined, and then if Snell returns to form, the Bucs have two option years for what should be reasonable prices. If the Pirates can sign McLouth, Maholm or Doumit to contracts along these lines, then I'm all for it even though they're all coming off unexpectedly good years.
UPDATE: Vlad notices this article, which says that the Cardinals might pursue Matt Capps as they search for a closer.
UPDATE II: The Post-Gazette says the Bucs have talked to the Marlins about shortstop Robert Andino, perhaps in a trade for Ronny Paulino. It's hard to tell for sure because the Marlins kept promoting Andino even though he never hit anywhere, but he probably can't hit at all. I expect that when you trade someone like Paulino, you can't expect much in return.
UPDATE III: This isn't directly Winter Meetings-related, but one blogger argues that McLouth is worth about $11.5 million per year. (Via Primer.)
UPDATE IV: The Palm Beach Post confirms the P-G's reporting about Andino and also mentions that the trade may be Andino for Paulino. The Post reports that Andino was signed by Marc DelPiano, who was recently hired by the Pirates as a special assistant to Neal Huntington. Andino also worked with former Marlins infield coach Perry Hill, another recent Pirates hire.
By the way, if you're inclined to be intrigued by Andino's .287/.356/.497 line at Class AAA this year, keep in mind that Albuquerque is the best place to hit in all of minor league baseball and that Andino had a 1.145 OPS at home and a .501 OPS on the road in AAA this year.