The 10 biggest what-ifs in Dallas Cowboys history

5. What if Bill Parcells left after 3 years and they kept Sean Payton?

Back in 2006, the Cowboys were wondering what would happen with their head coach. Bill Parcells, who was 64 at the time, had just finished his third campaign with the franchise and went 9-7 — following a 6-10 season prior to that.

Parcells, who was known for leaving in the middle of his contracts, was rumored to have one foot out the door. Despite this, Jerry Jones wanted him to return and found a way to convince Parcells to come back.

The two sides agreed to a new two-year deal and that cost Dallas one of the best young coaches in the game.

While Jones was busy trying to convince the coach with the big name to stick around for more mediocre football, other teams were trying to land Sean Payton. Dallas kept the man in his mid-60s and Payton, who was just 43 at the time, signed with the New Orleans Saints.

Parcells went on to coach Dallas to another 9-7 season while Payton went 10-6 in New Orleans. He then went on to win 152 games over the next 15 seasons while bringing him a Super Bowl trophy.

Dallas, on the other hand, saw Parcells leave with a year left on his deal. They've since endured Wade Phillips, Jason Garrett, and Mike McCarthy — with very little success in the playoffs.

Perhaps if they allowed Parcells to leave, they could have kept Payton and had the same run he did. Maybe Payton's coaching prowess with the allure of the star could have been enough to bring even more than one title. Or maybe Jerry Jones would have messed all that up as well.

We'll never know since Jones allowed one of the best young minds in the game walk in favor of a coach who dominated in the late 1980s.