Kenny Pickett’s recent comments about his time with the Philadelphia Eagles may have been intended as a compliment to his former team, but they also cast a shadow on his tenure with the Pittsburgh Steelers. Speaking to reporters on Wednesday, the new Cleveland Browns quarterback reflected on his stint in Philadelphia, saying, “I’m extremely grateful for my time in Philly. I think I was shown how it was supposed to be done from the top down, really. So when you get a chance to see what winning’s supposed to look like and how it should look on a day-to-day basis, not just on Sundays, I think it will pay dividends for me in the future.”
Browns QB Kenny Pickett said year with Eagles showed him how things are supposed to be done. pic.twitter.com/1EoSMPR8UX
— Scott Petrak ct (@ScottPetrak) May 28, 2025
While Pickett’s remarks seem to praise the Eagles’ organization, they subtly highlight deficiencies in his experience with the Steelers, where he played from 2022 to 2024. During his time in Pittsburgh, Pickett threw for 4,474 yards and 13 touchdowns, leading the team to a respectable 14-10 record in his starts. However, the Steelers failed to secure a playoff victory, a drought that has plagued the franchise since 2016. The organization’s impatience with Pickett’s development became evident when they signed veteran quarterback Russell Wilson to a one-year deal in March 2024, effectively sidelining the former Pitt star. Shortly after, Pickett was traded to Philadelphia.
It’s hard to blame Pickett if there’s a hint of resentment in his words. The Steelers’ lack of commitment to nurturing their young quarterback contrasts sharply with the Eagles’ winning culture, which culminated in a Super Bowl victory. Whether intentional or not, Pickett’s comments underscore a stark difference between the two organizations: Philadelphia’s ability to foster success “from the top down” versus Pittsburgh’s ongoing struggles to recapture postseason glory.
Now, as Pickett vies for the starting role with the Cleveland Browns, his time with the Eagles may prove to be a turning point. The lessons he absorbed in Philadelphia—where winning is a daily standard, not just a Sunday goal—could shape his future performance. Meanwhile, the Steelers are left to ponder whether letting Pickett go was a misstep, especially as their playoff drought continues. Only time will tell if Pittsburgh’s decision will haunt them or if Pickett will prove they were right to move on.