I loudly opposed the Romo extension in 2013 for this exact reason, and got blasted on here. I saw an aging QB who would never last the life of that extension, and wouldn't be worth the middling success he provided while under contract. If you remember, this extension came after that 2012 win and in week 17 game in Washington where Tony absolutely **** the bed. After that game, I had lost faith in Tony being the guy who could deliver a playoff run.
I remember the countless arguments on here debating whether or not "clutchness" was a real thing. People laughed at those who said Tony chokes under big pressure situations. The reality is there are human elements to this game, and for whatever reason Tony's nerves often got the best of him in big moments. He won 2 playoff games in his decade as QB here, and there was no way he was ever going to string together 3 or 4 of them in a post season run. You need to be consistently great under high pressure situations to have a chance at a championship; Aikman had it, Roger had it... Tony didn't.
I appreciate what he gave to this franchise, but he just wasn't the guy many wanted him so badly to be.