Wow! Drew talk can still generate 10 pages here, all these years later.
Count me among those who think he was overrated in New England. He rested upon the laurels of his pedigree: Big, tall, strong arm, No. 1 pick of the draft, "parenting with dignity", blah blah blah.
Those who support him still point to the same things: "classy", "full-page ad", "MINNESOTA GAME!!!", "pin-in-his-finger games", "helped save the franchise". Did I get them all?
To answer the original poster's question, if Drew won a Super Bowl in Dallas, I wouldn't feel happy for him. I don't think he's the classy guy he's been made out to the be. Like others mentioned in this thread, books like "Won For All" and "Patriots Reign" showed Bledsoe wasn't such a good soldier after all. He even went behind Belichick's back up to Robert Kraft. That's not being a team player; that's looking out for number one.
I admit that there were times in '93 and '94 when Bledsoe showed flashes of Marino-like ability. He even was able to make his teammates better in '94 when the team got high production out of the likes of Michael Timpson, Leroy Thompson, Kevin Turner and Vincent Brisby. But then, in '96, when he was surrounded with some nice talent (Martin, Coates, Glenn, Jefferson, Byars, Meggett), he had a lackluster playoffs. If he really was the player he was billed to be, he should have shined then. I think there were many QBs of that period who could have done more with the arsenal the Pats had. Oh but wait, if only Drew had a decent offensive line, right?
And given how close the team came that year, that's when the excuses started with all of us: "Drew's really gonna break through this year. This will be the year it all comes together." And then when different players starting departing the team, that became the excuse ("If only we had a decent running back").
Bledsoe deserves our contempt because despite being extremely well-paid, well-loved by fan and owner alike, and with special privileges not granted to the rest of the team (e.g., pay raises for Drew buddies), he never put team first. He never worked to improve his game (Montana, here I come), he never took the mantel of leadership when it was obviously needed ("Bruce Armstrong is our leader"), and although maintaining a humble demeanor in public, he let it be known through his media kissups that what was wrong with the team was never his fault.
If Bledsoe finally gets it together (some 13 years into his career), plays to the standard we were led to think he personified, and the result of his play leads the Cowboys to a Super Bowl win, then I'd have to say good for him. But as a Pats fan, I'd think, "Where was that effort ten years ago?"