Steelers legend Terry Bradshaw publicly criticized the team in December 2023 for trading Pickett after only two seasons, questioning the rationale and emphasizing the importance of protecting the quarterback for success.

Kenny Pickett, drafted 20th overall in 2022 to succeed Ben Roethlisberger, has faced challenges establishing himself as a starter, with comparisons drawn to quarterbacks like Baker Mayfield and Sam Darnold, who found success after early struggles.

Despite his struggles, critics argue that Pickett's situation could improve if the Steelers focused on building around him, especially by strengthening their offensive line, as success for first-round quarterbacks often depends on supporting talent.

Bradshaw highlighted that the Steelers' decision to trade Pickett, a first-round quarterback, after such a short period has left the team still searching for a reliable quarterback.

During his time with the Steelers, Pickett accumulated 4,474 passing yards, 13 touchdowns, and 13 interceptions over 25 games, reflecting his ongoing development.

In 2024, the Steelers signed veteran Russell Wilson, which led to Pickett being traded to the Philadelphia Eagles, where he served as a backup during their Super Bowl LIX victory.

While with the Eagles, Pickett was a backup to Jalen Hurts, who led the team to a Super Bowl win, before being traded again in March 2025 to the Cleveland Browns.

Bradshaw advocates for the Browns to focus on building around Pickett, especially by improving their offensive line, to give him the best chance at success.

Bradshaw criticized the Steelers for mishandling Pickett's development, asserting they failed to provide the necessary support and talent to help him succeed.

In December 2023, Bradshaw emphasized publicly that protecting the quarterback is crucial for success, aligning with his criticism of the Steelers' handling of Pickett.

As of July 2025, Pickett is competing for the starting quarterback role with the Browns, facing off against veteran Joe Flacco and rookies Dillon Gabriel and Shedeur Sanders, marking his third team in four years.