Charles Robinson of Yahoo Sports reported the deal will be "very economical," given the Saints' cap situation. Winston spent his first five seasons with the Tampa Bay Buccaneers and is coming off a roller-coaster campaign. He led the NFL with 5,109 passing yards to go along with 33 touchdowns and 30 interceptions, becoming the first player to throw 30 touchdowns and 30 picks in the same year.
New Orleans was not considered a likely landing spot for Winston after the team re-signed Brees and placed a first-round tender on Taysom Hill. The expectation was that Hill would be Brees' primary backup for the first time in his career. Mike Florio of Pro Football Talk reported in January the Saints envision Hill as their starting quarterback once Brees retires.
While this may simply be a case of a team taking advantage of a low-cost opportunity, it does cast doubt on the Saints' faith in Hill as a passer. Hill has only thrown 13 passes during his three-year NFL career. The Saints have found their most success with him as a gadget player, particularly when he lines up at wide receiver.
When given the chance to see how Hill would look under center last season, the Saints instead allowed Teddy Bridgewater to start five games. It's likely Winston will slot into Bridgewater's role, sitting out games entirely if Brees is healthy but moving into the starting job if he gets hurt.
Brees signed a two-year, $50 million contract with the Saints in March. He plans to join NBC Sports at the end of his NFL career, per Andrew Marchand of the New York Post.
Winston will look to use the 2020 season to learn under Brees and coach Sean Payton, erasing the memories of his turnover-happy Tampa ways before re-entering free agency in a year. For all the fretting about his turnovers—his 111 turnovers are the most in the NFL since 2015—there are few who deny his talent. He also underwent LASIK eye surgery during the offseason, a move that corrected the nearsightedness he's been playing with his entire career.
There is plenty of reason to believe taking this gap year will be beneficial, and Winston will hit free agency a year from now at age 27 ready to be a starter again.