So Trent Dilfer > Tony Romo right? Doug Williams > Dan Marino?
It's a team sport. Romo had a better skill set and more talent than Troy did. Not saying Troy wasn't also great in his own right, but he got lucky being on the right team at the right time. Didn't say his career was lucky in terms of his talent.
I loved Troy but for the most part, he did have better Olines, better WR's, better RB's (hall of famers) and better D's (#1 D on his 1st SB) and of course a much better HC in his SB years than Tony ever had. I' argue that only Witten was better at his position than what Troy had with Novacek in his SB years.
So even though Troy won 3 SB he had much better teams than Tony ever did, I don't think anybody could argue that.
Ask yourself this, if you switch Tony and Troy, would the Cowboys have won 3 SB in the 90's with Tony? I'd say there would be a good chance to have at least 2, on the other hand would Troy have won a SB with the Cowboys from 2006 to 2014? I would say no freaking way.
Temas matter, luck matters, Troy had a ton of luck with those teams, Tony on the other hand didn't.
I am not saying Tony > Troy btw, I see both of them as great QB's.