Oh, I think it's pretty clear he was worse than Ryan. I don't see how that's debatable. Smith did some things pretty well; the draft and international signings. He also picked up a few nice FAs that helped the 2010 team enormously. But his MLB transactions with opposing GMs were varying shades of disastrous. They weren't just kinda bad, they were "OMG WHAT ARE YOU DOING" bad. Santana for Gomez + junk Garza/Bartlett for Young + junk Capps for Ramos Hardy for Hoey Getting Hardy for Gomez was a nice move but any goodwill he earned from that was washed away with the Hoey deal. He was put into a tough spot with Hunter and Santana but that still doesn't mean he gets a pass on not making a good deal with the Mets. And Nishioka... Well, we all know the results of that blunder. Ryan's conservative nature is frustrating but at least it means he never pulls off any one of those trades, all of which hurt the team both in the short term and the long term. Smith took risks, which is sometimes the right thing to do... but his risks were often ill-conceived and they really hurt the team going forward. Fun fact: Trevor May's 2014-2015 seasons are worth more WAR than the return on Santana, Young, Capps, and Hoey combined.* Everyone else was under replacement value with the Twins, which negated the wins brought by Gomez. *this was very quick eyeball math, feel free to dispute this claim... either way, it's close.