Signed by the Houston Astros as an amateur free agent on 2 July 1995, he was selected by the Florida Marlins in the rule 5 draft on 13 December 1999, then immediately traded to the Minnesota Twins for a prospect.
Agent Peter Greenberg negotiated a record-breaking six-year, $150 million contract for Santana after he was traded to the New York Mets. (February 2008).
(January 29) The Minnesota Twins agree to trade Santana to the New York Mets for four prospects.