Just one day after Brees announced his retirement, Winston and the Saints reached agreement on a one-year deal worth up to $12 million, a league source told ESPN's Adam Schefter.
The former No. 1 overall NFL draft pick and Heisman Trophy winner spent his first five seasons as a starter with the Tampa Bay Buccaneers, before signing a one-year deal in New Orleans last summer to try to revive his career as the Saints' backup.
Although Winston played sparingly, the Saints were impressed enough to bring him back to compete with Taysom Hill for the starting job this year.
"Who Dat! #NOLA #DreamForever," Winston tweeted Monday evening.
Sources told ESPN's Jeremy Fowler that the Chicago Bears were serious suitors for Winston in Monday's free-agency process, before he picked the Saints.
The Saints will have to carve out a bit more salary-cap space before the start of the new league year on Wednesday. They began the offseason nearly $100 million over the cap but had whittled that figure to around $10 million by the start of this week.
Winston, who turned 27 in January, went 28-42 as a starter with Tampa, completing 61.3% of his passes with 19,737 yards, 121 touchdowns and 88 interceptions. He displayed some dynamic highs and lows during that tenure -- especially in 2019. That year, he led the league with 5,109 passing yards but also became the first quarterback in NFL history to throw at least 30 touchdown passes and 30 interceptions in the same season.
Turnovers have been Winston's biggest hurdle, with a league-high total of 111 from 2015 to 2019.
When the Buccaneers elected to move on to Tom Brady, Winston decided to try to revive his career in New Orleans. He signed a one-year deal worth just $1.1 million plus incentives because he said he wanted to get a "Harvard education in quarterback school" under coach Sean Payton and Brees.
Winston didn't get much on-field experience in New Orleans behind Brees and Hill. But Winston did make his best play of the season when he completed a 56-yard touchdown pass on a trick play in the Saints' playoff loss to his former team. Winston was 7-of-11 for 75 yards in the regular season with no touchdowns or turnovers.
Payton made it clear after the season that the Saints wanted to re-sign Winston and let him compete with Hill for the starting job following Brees' retirement. Payton said Winston was "fantastic as a leader."
Winston was suspended for the first three games of the 2018 season after an eight-month NFL investigation concluded that he engaged in detrimental conduct in March 2016 by touching a female Uber driver "in an inappropriate and sexual manner without her consent." A settlement was reached in a separate lawsuit.