That extension doesn’t look good now but I don’t recall thinking it was a bad idea then. Part of the risk for a mid market team is that it isn’t reasonable to throw away these sunk costs.
They committed 13 years to Hughes, Santana and Nolasco and have a good return on 3 of those 10 years thus far. That is not a recipe for success.
They gave him a 5 year extension one year into a 3 year contract. What was the rush? He wasn’t going anywhere. Decisions like that are exactly why Terry Ryan was fired.