Winston enters the 2026 season as the clear backup to 2025 first-round pick Jaxson Dart with Russell Wilson retired. Although now entering his age-32 campaign, Winston has consistently shown the ability to generate production when called upon, compiling 567 passing yards, two touchdowns and two interceptions in three appearances in 2025, while also adding 23 rushing yards and a score. Dart battled injuries during his rookie season, in part due to his aggressive play style, which makes Winston one of the more likely backup quarterbacks to see action at some point in 2026. As recently as 2024, Winston appeared in 12 games with the Browns, making seven starts and totaling 2,121 passing yards with a 13:12 TD:INT.