According to Brees, one of the turning points was his first playoff game with the Saints in that first year, a 27-24 victory over the Eagles in a divisional-round game at the Superdome on Jan. 13, 2007.
"That was the biggest game of all of our careers at the time," Brees recalled this week at practice.
Brees noted that his initial Saints team had many players with similar backgrounds.
"We had guys coming from a lot of places that were unwanted or who probably hadn't had a whole bunch of success," he said. "Coming here was a fresh start for a lot of us."
Brees was coming off shoulder surgery and was a free agent. Most teams were skeptical of the injury, not to mention that the 6-foot, 209-pound Brees was - and remains - among the smallest NFL quarterbacks.
In that win over the Eagles, Brees was an efficient 20 for 32 passing for 243 yards and a touchdown. The win sent the Saints to the NFC championship game, which they lost at Chicago, 39-14.
"To have that opportunity, then to host the divisional-round game and to beat Philly in the fashion that we did and have an opportunity at the NFC championship, those are all great memories," Brees said.
Three seasons later, Brees led the Saints to a 31-17 Super Bowl win over the Indianapolis Colts and has continued piling up wins and staggering statistics.
This season, Brees threw for 5,162 yards and 39 touchdowns. It was the fourth time Brees has thrown for more than 5,000 yards in a season. No other quarterback in NFL history has done it more than once.
Since his first year with the Saints, in 2006, Brees leads the NFL in several categories, including passing yards (38,733), touchdown passes (283), and completion percentage (67.3).
"It gives you extreme confidence having Drew," said veteran Saints receiver Lance Moore. "You have one of the best in the game leading you every day."
From their debut season of 1967 through 2000, the Saints competed in just six playoff games, winning one.
Since Brees' arrival, the Saints are 5-3, with the Super Bowl title and two trips to the NFC championship game. This year is the fifth time in his eight seasons that the Saints are in the playoffs.
Payton said there are a number of reasons Brees gives the Saints such a comfort level.
"His experience and his durability and all of those things are helpful," Payton said. "I think not only for the head coach, but I think the other players in the huddle on any given play."
The durability factor may be the most underrated. During his eight seasons in New Orleans, Brees has started 127 of 128 regular-season games and all eight playoff games. This season he earned his seventh Pro Bowl berth with the Saints and eighth overall.
"Drew is a Hall of Famer," Eagles coach Chip Kelly said in a conference call with Saints reporters. "He has such a great understanding of Sean's offense, which is probably the most difficult offense to defend because they attack you both vertically and horizontally."
Brees, who will turn 35 on Jan. 15, has shown no signs of slowing down.
"He makes mistakes like the rest of us, but he makes a lot less mistakes than the rest of us," Moore said. "That is what makes him so great."