I don't like to look at a free agent signing strictly from a WAR/salary perspective. It leaves out a bunch of context.
You need to consider many factors, such as:
How valuable was the players production to the team?
How replaceable was that production?
What would be the cost of that replacement?
How would the money spent on their player be better spent?
Would the savings from signing a cheaper replacement be enough to improve the team?
Was the players contract preventing the team from making other improvements to the team?
And so on.
I don't like paying older pitchers market value, and I wasn't happy with the extensions at the time. But I think a more detailed analysis of the extensions and their context is needed before calling them a bust.