While I won't go out of my way to say the old front office (but remember 2009 was Smith's administration, not Ryan) was good at drafting/acquiring talent, this is a bit unfair. Almost all of baseball passed on Mike Trout (hilariously, including the Angels as they picked 24/25 and Trout went 25th), Gibson was a fine first round choice. Currently, out of all 2009 first round picks, he's 7th in overall rWAR. It's definitely not a jaw-dropping pick but a team that chooses a Kyle Gibson career in the first round every year will be a perennial winner.
Now, if you want to talk about horrible evaluation of talent, there's always the drafts of 2013-2015...
But back to 2009, that was actually a BANNER YEAR for the Twins. They drafted Gibson and Dozier while they signed Polanco, Kepler, and Sano to international contracts all in that same year. That's a stellar year for a baseball organization. Those guys are worth 73 career rWAR and still counting upward every season.