I don't know, I think his draft record (2010 especially) is better than most and that success has allowed him to make the type of deals that are future based. But in spite of that, I don't think he evaluated the current group very well, namely thinking they could deal Mankins and survive, or that they have some infinite timeline for success. Brady can still function at a high level, but he needs help. Would Mankns blocking the interior be the difference? Hard to think one lineman could have that type of impact, but giving a guy like Brady 0.2 more seconds in the pocket could be the difference between high fiving him or scraping him up off the turf.
That and the talent in his receiving corps has been in steady decline over the years. I don't pay enough attention to the NFL salary cap issues of each team to know whether previous roster decisions were necessary, or whether Brady's salary demands have directly affected who they could bring in at WR, but either way, they've done a brutal job assessing that position the last few years. Why have a stud QB you pay 20 mil if you surround him with Edelman and a 1 legged Gronk? That's like putting bald tires from a scrap yard on a Ferrari.