Santana was one of the best pitchers in baseball while with the Twins. From 2004-06, he led the league in strikeouts, ERA+ and WHIP all three seasons, winning the Cy Young in two of the three years. After the '07 season, he was traded to the Mets and signed a six-year contract extension. His time in New York was not nearly as successful though as he battled major shoulder issues. When he was healthy, he was great. But he missed all of the 2011 and 2013 seasons after undergoing major shoulder surgeries.
He's now looking to come back from that second surgery and has received interest from a number of teams. In order to consummate a reunion with the Twins though they will have to make some moves to find room for him. As it stands, the Twins have Ricky Nolasco and Phil Hughes, both big free agent signings this winter, at the top of their rotation, with Kevin Correia and Mike Pelfrey at Nos. 3 and 4. Their fifth rotation spot is setting up to be a spring training battle among Scott Diamond, Samuel Dedundo and Vance Worley. Dedudo had a nice 3.83 ERA in 18 starts last season and figures to be the early frontrunner. All three are out of options though, so the Twins would likely have to find new homes for all three of them if they want to bring back Santana.