6. What if Sean Payton landed Tony Romo?
Before the Saints signed Drew Brees, they actually went after a different quarterback. Sean Payton, who had spent three seasons as an offensive coach with the Dallas Cowboys before taking the job in New Orleans tried to bring someone along with him.
In a 2015 biography, Bill Parcells (the head coach in Dallas during that span) wrote that Payton nearly convinced the Cowboys to trade Tony Romo to New Orleans. Of course, the trade never happened and Romo has since become the No. 1 passer in franchise history and the Saints found their own franchise leader in Brees.
Before any of that happened, however, Romo was entering 2006 without a passing attempt under his belt. Despite this, Payton believed in him. In fact, he was the one who wanted Parcells to sign Romo as an undrafted free agent in 2003 after he followed his career at Eastern Illinois — which was Payton's school as well.
Payton offered a third-round pick for Romo, which would have been fair compensation at the time. But with Drew Bledsoe being 34 years old that season, the Cowboys weren't willing to pull the trigger. They're glad they didn't since Romo took over as the starter after 6 weeks and New Orleans is happy with how things turned out as well.
The question is whether or not all the success they had with Brees would have been different if Romo were the starter. While there's no question Brees had the better career, he entered 2006 with some questions following his departure from San Diego. Perhaps Romo would be the one with the ring and would be viewed differently had Payton's original plan panned out.