The Hughes extension is a good snapshot of some of TR's weaknesses IMO. 1. An over-commitment to free agent acquisitions. Particularly the multi-year contract signees. Hughes had an outlier performance, something other GMs would recognize. His trade value probably wasn't that high, but I have to believe a trade opportunity would have been there, if Ryan had pursued it. But he has built this image of the Twins as the anti-Marlins. It sounds callous to say, but sometimes the best thing for the franchise, is to uproot a player and ship him off. They do it every time they recall or option the Buxtons of the system- Buxton has a wife and kid too. But for whatever reason TR cultivates this image that if you sign with the Twins you don't have to worry about being flipped and I believe that costs him trade opportunities. 2. Poor appreciation for the forces of regression. Kinda ironic because a big part of the justification for signing Hughes in the first place was, his HR/FB would normalize into something resembling league average if he moved into a more league average home park. But Hughes' HR/FB in 2014 wasn't just normal, it was 6th-lowest in baseball. A correction in 2015-18 seemed completely possible, if not likely. And then there was the K/BB rate which was the GOAT, practically screaming regression. 3. Poor appreciation for age related decline. Again, sort of ironic because the other appealing thing about the original Hughes contract was that Hughes was one of the younger free agents in the class. But instead of letting him walk at age 30, Ryan made sure he locked Hughes well into decline years. 4. Lousy timing. As mentioned already, there was no point in extending a player likely to regress, with 2 years remaining on the contract. Not trading him- okay, maybe a deal wasn't there. Maybe. But to go so far the other way and extend the guy? Just completely unnecessary. It turned an asset into a liability, and will handcuff the team when all the young talent they've drafted during this downturn is ready to audition in 2016-2018.