Thought I'd check in on the progress of this thread. Now people are spouting off nonsense about the possibility of having won more Superbowls with Brees at QB. Unreal.
Drew Brees is a very good quarterback, good enough to win a ring of his own with a much lesser roster and organization around him than Brady usually has to work with. With Belichick's roster building talent around him I think it's entirely possible to propose that he could be in the same universe as Brady currently is.
Brady's career is a combination of talent and opportunity. Brady is excellently talented in ways that are hard to measure. But Brees also has many of the same talents, he's a good quarterback not just for the raw measurables, which as probably better than Brady's if we're honest, but he also has many of the same intangible assets as well. Given the same environment to develop in that Brady had, what could Brees have been? Is it possible that specific situations that went against Brady might fall differently with a different quarterback? Hard to say. Also hard to rule out. Certainly not worth merely dismissing with an ignorant guffaw.
If the franchise trusted Bledsoe, Brady would have been stuffed back onto the bench the first chance Belichick had. He clearly trusted Brady more than Bledsoe irregardless of Bledsoe's injury. Remember, one of Belichick's greatest abilities is to scout the talent on his own team. He had an idea what Tom Brady was earlier than most of us. And he clearly had a concept that Brady had some attributes that made him worth extending his audition even when his putative starter was healthy again. I don't think BB would do that just because Brady was still winning. Not if he thought that Bledsoe could win too. Clearly there were trust issues between Belichick and Bledsoe that led into that particular decision.
If the franchise hadn't had a very interesting young prospect to fill in for Bledsoe after the 2000 season and he still distrusts Bledsoe which he clearly did, repositioning the franchise around one of the QB's from the draft is a standard move. Of the draft candidates available in 2001, Brees is the most reasonable choice.
I think it's very likely that without a viable in-house replacement and with no love lost for Bledsoe, Belichick goes after Brees either by trading down or by swapping Bledsoe for a low first, and with Brees on the roster, BB has easily enough quarterback to work with to go win some rings. Maybe not five, but some number, and Brees is good enough that 5 isn't off the table. With Belichick's roster building ability, and a very talented quarterback to work with, I think either Brees or Brady would have been in the GOAT conversation by this point and would have, by dint of being talented quarterbacks in a winning organization, earned their place in the conversation.
The fact of the matter is that so many of Brees' best years have been wasted that it's really tough to measure him properly against Brady. With a better organization Brees could have been one of the all timers. Arguably he's still on the cusp of that conversation. But the Saints' mishandling of their roster has left him something of a forgotten man despite his obvious skill. That would not have happened to him in an organization run by Bill Belichick.
Brady is probably objectively better than Brees, I will say that. But certainly not so much better that Belichick can't craft a roster that Brees could win multiple rings with. And he could have had him if he wasn't satisfied with his quarterbacking options at the 2001 draft. That's all I'm saying.
