Cuddyer has been around since 2003 and has had one solid season in 2006. He is 32 and is starting to come off injury prone. Delmon Young is 23. In his first 2 full seasons he has had a career average of .292.
It will only be a matter of time before he has a monstrous breakout year. The Twins might end up trading Cuddyer somewhere else, because Gomez may still be progressing the only way he will continue to progress is if he plays.
Span is by far the best of the four outfielders and should be the starter in center field. Gomez should be in left. Then Young can go back to his natural position in right field, then he can focus on his offense. Cuddyer has been average at best when healthy.
Delmon Young is the better option with the stronger arm for right field. The wise thing for the Twins to do is to trade Cuddyer and try and get maybe a solid set up man or package him with Blackburn and try to get another solid pitcher, not that Blackburn isn't a solid pitcher.
What they should do is trade Cuddyer with Punto and try to get an every day shortstop. Punto is average on offense at best, is definitely gold glove worthy on defense. We need someone who can be consistent with both.
That could be Matt Tolbert, but how long will it take for him to develop?