Well, I do like the idea of stealing O-Dog to play 2B this late in free agency. Nothing personal against Mike Fontenot, but their offensive production is close to a wash while Hudson's glove is in on a much higher level. In any case, there are probably people within the organization that are on both sides of this, but its certainly been considered. One article mentions as much, Nick Cafardo of the Boston Globe from 2/8/2009:
"Orlando Hudson, 2B, free agent: It's amazing that a player of this caliber remains unsigned, but lining up are the Cubs, White Sox, and Dodgers. A few Cubs organizational people really want Hudson, but the impending transfer of ownership from the Chicago Tribune to Tom Ricketts may hinder GM Jim Hendry's ability to do anything until it's complete."
I'm not trying to say that everyting the guy says is fact, but I would have to assume that he consulted various sources before he published it in an article in the Boston Globe. What he's suggesting isn't all that wild either. Fontenot is a nice 2B, but if the team can add an All-Star & GoldGlover at half-price and work him into the current payroll then the idea is probably worth exploring. Nothing says that Fontenot couldn't still be a valuable utility player and bat off of the bench as well as insurance to guard against various injuries. If the team can add Hudson for near the same cost as what they would have paid DeRosa if they kept him, then I would say that is one hell of a steal. They sign Hudson the team gets; a replacement for DeRo at relatively the same cost, 3 pitching prospects from the Indians, and Mike Fontenot is still on the roster as well --> What exactly does the team have to lose?