News of Winston's deal was first reported by Yahoo Sports' Charles Robinson on Sunday.
While the terms of the deal were not officially announced, Robinson reported that the deal will be "very economical" and completed shortly. Winston reportedly was not guaranteed that he would be New Orleans's No. 2 quarterback, as he will instead be competing against both Taysom Hill and 2020 seventh-round pick Tommy Stevens. Drew Brees will again be the team's starter as Brees also reached a two-year extension with New Orleans this offseason.
According to the NFL Network's Ian Rapoport, Winston turned down a more lucrative offer elsewhere to instead have the opportunity to learn from Brees.
The 26-year-old Winston had spent the first five years of his NFL career with the Buccaneers, who drafted the Florida State product first overall in the 2015 NFL draft.
Through five seasons in Tampa Bay, Winston threw for nearly 20,000 career yards, but his accuracy proved to be a concern throughout.
Last season, he finished the year with 5,109 passing yards, 33 touchdowns and 30 interceptions. He was the fifth quarterback to throw 30 interceptions in a season, but just the first in league history to throw for 30 or more touchdowns and 30 or more interceptions.
Winston had just one winning season throughout his five years in Tampa Bay, doing so in 2016 when the club finished 9–7. The team failed to make the postseason with him under center.
The Buccaneers' decision to move on from Winston comes as a result of the team signing six-time Super Bowl winner Tom Brady this offseason.
This offseason, Winston underwent LASIK eye surgery.
“Jameis did not want to count out any options that he had that could possibly help him with the game he loves so much,” Winston's spokeswoman Denise White told ESPN's Adam Schefter in early February. “He doesn’t want to miss out on any opportunity that presents itself.”
In Buccaneers head coach Bruce Arians' final press conference of 2019, the veteran coach commented on Winston's eyesight.
“He can’t read the scoreboard but he can see the guys in front of him,'' Arians said. "So he’s alright.”
ESPN's Jenna Laine previously noted that Winston has struggled with nearsightedness and that while the QB was at Florida State, television cameras often panned to him squinting. While with the Seminoles, he won both the Heisman Trophy and BCS Championship in 2013.
Winston appeared to have a limited market this offseason and with no starting jobs available, decided to join New Orleans.
After losing in controversial fashion in the 2018 NFC championship, the Saints entered last year with Super Bowl expectations. New Orleans matched its 13–3 record in 2019, overcoming a Brees thumb injury that knocked the quarterback out for five weeks during the regular season.
But despite posting back-to-back seasons with 12 or more wins for the first time in franchise history, the Saints lost 26–20 to the Vikings in the wild-card round of the playoffs.
Despite Brees agreeing to a two-year extension, he also reportedly reached an agreement with NBC Sports to serve a prominent role in their football broadcasts in a contract that will begin after he leaves the NFL.
New Orleans made just four picks in the 2020 NFL draft, selecting Michigan center Cesar Ruiz, Wisconsin linebacker Zack Baun, Dayton tight end Adam Trautman and the aforementioned Mississippi State quarterback Stevens.
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