A victory in Super Bowl XXXIV would have surely cemented his place as the teams best player in franchise history.
The loss, however, was followed by years of conflict and injury, and it seemed as if McNabb would never reach the potential that seemed so promising in his first five years.
As the second overall pick of the 1999 Draft, McNabb has always garnered the most criticism for every loss he's been a part of.
His final years in Philly were plagued by rumors about leaving the team, despite strong showings in his final two seasons there.
After suffering through his worst season with the Washington Redskins last year, including several run-ins with head coach Mike Shanahan, critics became less hesitant in stating that the former Syracuse star was done.
Many, including McNabb himself, however, still believed he had a lot left in him.
Then came the Minnesota Vikings calling this summer, in what was probably the six-time Pro Bowlers last chance to start for a team.
Multiple poor performances and a 1-6 start resulted in his benching and subsequent release from the team, upon his own request.
Though he went unclaimed on waivers, and things seemed lower than ever for McNabb, opportunities have opened up for him.
In Chicago, Jay Cutler will most likely miss the rest of the season, and his replacement, Caleb Hanie, could not be playing worse football.
The prime chance for McNabb to revive his legacy and career would be to get the Bears into the playoffs.
Devin Hester has already said that there would be no point in having McNabb or another veteran quarterback come in because of the complexity of Mike Martz's offense, but it doesn't seem like Hanie's got the hang of it either.
If McNabb performs well, then he is once again seen as one of the game's toughest and best competitors.
If he fails?
Then he did so on a Bears team that has close to no talent on offense and is currently lacking close to 40 percent of their offense in Matt Forte.
Should Donovan McNabb retire or sign with a team?
The one thing McNabb has done consistently in his career is not throw interceptions.
Prior to last season, the most picks he threw in one season was 13, which happened in his second year in the league.
If he can stay turnover free, then he would give Chicago a legitimate shot at making the playoffs.
The worst thing for McNabb would be to sit on the bench and act as an insurance for a team that is not in immediate need for him, like the Dallas Cowboys.
It would be an insult to the great career he's had.
If he continues to jump from team to team over the next season or two, then all those great years in the "City of Brotherly Love" will not be remembered elsewhere.
Unfortunately, it doesn't look like the Bears are willing to roll the dice on McNabb, and will remain with either Luke McCown or Hanie as quarterback.
Over the next week, some team probably will end up calling and asking for his services. "Mr. 4th-and-26" would be wise to decline.