Although the battle was close for a while, the 27-year-old Winston arguably offered more upside than the 31-year-old Taysom Hill -- and definitely made a stronger closing argument with his dynamic display Monday night.
Still, the Saints' decision hardly means all questions have been eliminated as they head into a season without Drew Brees for the first time in 16 years.
Here's a look at four questions that stand out most:
A more vertical Saints offense?
It didn't take long to see the element Winston brings to Payton's offense. His first of two deep touchdown passes to receiver Marquez Callaway on Monday traveled 53.3 yards in the air according to NFL Next Gen Stats -- the longest of any Saints TD since 2016.
When asked if Callaway was his first read, Winston's face lit up.
"Absolutely," Winston said. "As soon as I saw the safety cut [toward a shallow receiver], I'm letting it go. I don't like missing those opportunities."
We saw several similar throws from Winston throughout training camp, and we also saw Payton design a 56-yard TD pass from Winston on a trick play in the playoffs last season.
Conversely, we didn't see many of those throws in Brees' later years. In 2020, the Saints threw 29 passes that traveled 20-plus yards beyond the line of scrimmage, according to ESPN Stats & Information -- fewer than any team since 2014.
Obviously there is more to playing quarterback than arm strength. Brees is Exhibit A. But that doesn't mean Payton isn't excited to add some old tricks back into his playbook from when Brees was routinely throwing for 5,000-plus yards per season.
Almost every time Payton has been asked about Winston over the past two years, he has mentioned his "arm talent" and his leadership as two traits that stand out most. Several Saints receivers have also expressed excitement with knowing Winston might let it loose down the field even if they aren't the first read.
Winston didn't actually rely that much on deep balls during five years with the Tampa Bay Buccaneers. According to ESPN Stats & Info, he ranked 16th, 15th, eighth and 14th in the NFL in percentage of passes thrown 20-plus yards from 2015 to 2018. But he ranked second in 2019 at 16% while leading the league with 5,109 passing yards in his first year with aggressive offensive coach Bruce Arians. Of course, Winston also infamously became the first QB to throw at least 30 TD passes and 30 interceptions in that same season.
A riskier Saints offense?
Therein lies the rub. Winston threw 88 interceptions and lost 23 fumbles in 70 games with the Bucs. The Saints need to make sure he stays on the right side of that risk-reward formula.
So far, Winston has said and done the right things -- starting with his decision to join the Saints last year to get a "Harvard education in quarterback school" under Payton, Brees and offensive coordinator Pete Carmichael Jr.
Winston said the No. 1 thing he learned from Brees was focusing on making the right decision instead of trying to force big results. And you can count his total number of interceptions on one hand through four weeks of camp, while he has made a habit of checking down to safer throws (he did have a slightly underthrown deep ball picked in the first preseason game, though it bounced out of receiver Lil'Jordan Humphrey's hands).
"Sean Payton told us, 'Jameis will not play the same way he played in Tampa Bay, I assure you of that. I will not allow him to, and our system will not allow him to,'" said ESPN analyst Louis Riddick, who had a pregame chat with Payton as part of the Monday Night Football broadcast.
"The reason why you should be optimistic is simply because, one, Jameis is a good quarterback," Riddick said. "He always has been. He just needed to be better as far as his decision-making is concerned. And that's not always just about him. That may also be a function of the offenses he has played in. The other reason to be optimistic is that he is in a tried-and-true and productive system that has been proven to work."
What does this mean for Hill?
This is obviously a disappointment for the fifth-year pro, who has always stressed that his goal is to become a starting quarterback, despite his eagerness to help the team in so many other ways as a RB/TE/WR/kick returner/special teams coverage ace.
Hill went all-in to achieve his goal this offseason, gearing his workouts and practice reps solely toward playing QB. Listed at 6-foot-2, 221 pounds, Hill bulked up a bit in past years to take on some of those extra duties. This year he said he slimmed down to 215 to gain flexibility because "if I'm not going to be blocking defensive ends and backers and safeties and stuff, then I didn't need to carry the extra weight."
Still, it's hard to imagine Hill won't gamely step back into a similar role. Maybe the Saints won't ask him to do as much blocking or special teams work. But they will almost certainly keep designing packages for him as a read-option QB, runner and pass-catcher after he has racked up 613 rushing yards, 332 receiving yards and 16 touchdowns over the past two seasons.
That versatility is a big reason the Saints signed Hill to a two-year, $21 million deal as a restricted free agent in 2020. And you could argue that role is more important than ever since the Saints lost Brees, wide receiver Emmanuel Sanders and tight ends Jared Cook and Josh Hill this offseason -- and top WR Michael Thomas is currently out because of an ankle injury.
As for the future, Hill will be an unrestricted free agent in 2022 and may have to decide whether to keep pursuing QB opportunities elsewhere or potentially embrace his "slash" role on a more permanent basis.
What does this mean for fantasy?
Winston's emergence didn't shake things up much in ESPN's fantasy football rankings. Mike Clay, who produces ESPN's projections, said he already had Winston making 12 starts -- and only bumped that up to 14 because of the risk of a potential QB switch at some point. Clay only moved Winston up to QB 24.
"He can prove to be a fantasy steal," Clay said. "But at the same time, his pass-catchers remain a question mark and he's going to lose occasional snaps to Hill."
Winston's value increased more with analysts Matthew Berry and Field Yates, since both thought Payton might go with Hill to start the season. But neither was ready to make Winston a top-15 QB since he doesn't add much fantasy value through rushing yardage -- and since he could cede snaps to Hill in certain packages.
However, everyone agrees Winston enhances the value of New Orleans' pass-catchers -- especially running back Alvin Kamara, who is safer as the consensus No. 3 overall pick. And Callaway has soared into the top 50 among receivers after his breakout summer.