"I hope he comes back," Winston said during a Friday appearance on the NFL Network's NFL Total Access (via Grant Gordon of NFL.com) amid questions about the wideout's future:
"We talked briefly. And the thing about having a guy like DeSean Jackson; he's passionate, he wants to win. When you have a guy like that, really winning and losing really separates how he's going to react. He wants to be an important part in winning football games and he knows that he is a very important piece to winning football games. So if we were winning, he's a selfless individual and he's fine. But when you're losing and the guy feels like he's not getting taking advantage of, of course he's going to have something to say. That's just his make-up."
Jackson recorded 41 receptions for 774 yards and four touchdowns across 12 appearances for Tampa last season. Although his volume was low (3.4 catches per game), he led the NFL with a per-catch average of 18.9 yards, illustrating Winston's point about making big plays.
The 32-year-old Los Angeles native is under contract with the Buccaneers for 2019, but the team can release him and shed his entire $10 million cap hit, per Spotrac.
In January, the three-time Pro Bowl selection told TMZ Sports he wasn't sure what his future held.
"That's what I got an agent for, bro," Jackson said. "I don't know, I just go play, bro. That's all I worry about."
If Tampa does move on from Jackson, finding a No. 2 target behind Mike Evans will become a key part of the team's offseason to-do list under new head coach Bruce Arians.
Winston referenced having a speedster out wide to compliment their top receiver on NFL Total Access.
"When you look at B.A.'s offense, you always see a speed demon, you see a great guy, a possession guy, a guy that makes all your great plays like he had with Larry Fitzgerald," he said. "We have that with Mike Evans and it's going to be very unique to see Mike get moved around and set him up in different matchups for our advantage."
The Bucs haven't formally announced whether the receiver will be back for next season, though.