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When was the last time a Twins Rule 5 pick made the team for Opening Day? I honestly can't remember one since Santana.

That is pretty much correct. The Twins took Jared Camp with the first pick in that 1999 Rule 5 pick, and then traded him to Florida for the #2 pick (Santana). Here are their Rule 5 picks since:

 

2000 - Brandon Knight

2001 - None

2002 - Jose Morban (later spent time with O's)

2003 - None

2004 - Ryan Rowland-Smith (The Aussie has spent a lot of big league time)

2005 - Jason Pridie (was returned to TB, but obviously came back)

2006 - Alejandro Machado (spent year on DL, next year in Rochester, when healthy)

2007 - None

2008 - Jason Jones (spent one year in Rochester)

2009 - None

2010 - Scott Diamond

2011 - Terry Doyle