Payton showed the free-agent quarterback and his wife around the city - then got lost driving them back to the Saints' suburban training facility.
After a period of time steering aimlessly, he called for directions and was told to head in the opposite direction.
It might have been the only wrong turn Payton has taken since arriving here.
The rookie coach has won New Orleans over by encouraging the notion that his team can be a rallying point for a populace still rebuilding from Hurricane Katrina.
"We're not afraid of that," he said. "There's still a lot of work to be done in this city, as you know. We just hope we can give people a little kick in their step."
At the very least, he has given them a winner.
Only a year removed from a 3-13 record, the Saints have the NFL's top-ranked offense and will play in their first-ever NFC championship game against the Chicago Bears on Sunday. This transformation earned Payton Coach of the Year honors in his first shot at running a team.
"He's done a great job," said Brees, who joined up despite the vehicular misadventure. "He's got us playing an aggressive style, a very confident style."
What might be Payton's biggest accomplishment has been effectively juggling an abundance of talent on offense.
During the offseason, the Saints not only added Brees, but also stole Reggie Bush with the second draft pick and discovered receiver Marques Colston at Division I-AA Hofstra, taking him in the seventh round.
These newcomers joined a pair of solid veterans in running back Deuce McAllister and receiver Joe Horn.
"Sean and I talked about it early on," general manager Mickey Loomis said. "Clearly, he was chomping at the bit to use all these guys."
While the Saints also took steps to bolster their defense, the scoring potential intrigued a coach who had played quarterback at Eastern Illinois and apprenticed as an offensive coordinator for the New York Giants and a play-caller under Bill Parcells in Dallas.
Payton, 43, looks young - Parcells called him "Dennis the Menace" - and has been known to high-five fans in the front row at the Superdome. Yet he is more about tactics than personality.
In Brees, he found a leader after his own heart, smart and quick-armed, able to throw accurately off short drops to avoid the sack, a hard worker.
"Apart from the things you guys see," Payton said, "there's a lot of time spent with preparation and attention to detail that serve him well on game day."
Nuances have defined the New Orleans offense this season. With such a variety of talent, the Saints are constantly shifting personnel and formations.
"Sean Payton does a great job matching up, moving people around," said Jim Johnson, defensive coordinator for the Philadelphia Eagles. "All of that shifting and motion and all they do with skilled people, yeah, it's tough to prepare for them."
Bush serves as an example, having scored touchdowns as a running back, receiver and punt returner. His 88 catches set an NFL record for a rookie running back and fueled 1,523 all-purpose yards.
Defenses have struggled when he and McAllister have lined up together.
"When you have two running backs that are running the ball well, it poses another problem," Giants cornerback Sam Madison said. "They can put two backs out there and then come out and put Bush as a receiver."
They can also use him the way Southern California often did - as a decoy.
On one play during Saturday night's divisional game against the Eagles, the rookie was split wide, spreading the defense, and McAllister ran right for 28 yards. On another play, Brees faked a quick pass to Bush, then threw the opposite direction to Colston.
"The great thing about this team is that we don't have selfish players," Bush said.
It helps that Payton has spread the ball around enough to keep everyone happy. It also didn't hurt when the Saints won their first three games, including an emotional return to the hurricane-ravaged Superdome.
Players say they bought into the new scheme and gained confidence.
"Each time we go out there, it's like, 'OK, who's going to be the guy on this drive?'" Brees said.
David Wharton writes for the Los Angeles Times.