I had to step away for a bit, now I'm back to the Team Bill vs Team Tom battle:
I'd say after 2002 if they had another losing season.
There's video of Bob for one of those documentaries saying Bill was not ready to be a HC in '97.
The difference between the 96 team and the 2001 team was night and day for Drew. Drew was uncomfortable as heck in the 2001 offense being under center as much as he was because Woody couldn't snap the damn ball. They had to go out and get Mike Compton for crying out loud. Smith was not Martin, the line wasn't good enough for Drew to take deep shots, there was no TE and I can't remember why Glenn was MIA. Drew was just not a fit in NE anymore.
They got rid of old-overpaid players.
See above regarding Drew. The D was trending in the right direction to be good enough to keep them in games, but the O could've move the ball worth a damn with Drew.
They had a solid roster, but they weren't loaded. Aside from 2007, 2003 was their best roster.
That's sure a long time for a team that was just 2 years removed from the playoffs and with a soon to be $100M QB.