People should complain that you're arrogant and condescending instead.
Long winded diatribe above aside, all it takes to blow up your entire argument is Tony DeAngelo and his agent approaching Gorton and simply saying "We are only going to sign a one year deal, period, and we feel we should get $------" Furthermore, because only "one offer" (that we know of) was presented doesn't mean other offers weren't discussed by both parties. As a matter of fact, anyone can submit any arbitrary situation that COULD have happened and it's enough to blow up your "mismanagement" postulation. You're arguing about something you think SHOULD have happened but might never have been on the table for EITHER side. Contracts, like drafts, in retrospect are always a lot easier.
I completely understand the difference between RFA and RFA arbitration eligible contracts, term, term factoring in RFA and UFA years, etc... I really don't need you to explain anything to me to understand that you can still only guess as to what was being discussed during Tony's hold out despite what you say was a no choice situation. Term? $? Neither? Both?
There's nothing that you can "explain" because you weren't in the room, on the calls, privy to either sides position, or anything else. All you can do is speculate with what you have and you might think the Ola DeAngelo Contract Magic Wand Theorem® argument holds water, but it doesn't because you simply don't have enough information and, likely, never will.
You can reply again if you like, but this is where my position begins and ends. I'm not arguing, now, that in retrospect it wouldn't have been nice to wrap him up for 5 years but that's not the argument that I'm making. Furthermore, such a contract would've resulted in another transaction happening because the Rangers simply didn't have the space to do it at the time. Who's gone or who was bought out? Who was traded and who took their spot? It's pointless.