Kenny Pickett has plenty of love for Pittsburgh, where he enjoyed great success at the University of Pittsburgh before becoming the starting quarterback of the city's NFL team. He may not, though, have similar feelings about the Steelers, who unceremoniously traded him to the Philadelphia Eagles during the first week of free agency. 

Pickett penned a touching goodbye letter to Pittsburgh, but the note failed to mention the Steelers, whose decision to sign Russell Wilson ultimately signaled the end of Pickett's time in Pittsburgh. The Steelers then traded for Pickett's replacement (former Bears quarterback Justin Fields) a day after trading him to Philadelphia. 

It's easy to see why Pickett would have ill feelings towards the Steelers, who traded him after just two years and 24 starts. Initially, Pickett was told that he would face competition this summer before he was reportedly told that Wilson would be the team's starting quarterback in 2024. 

Pickett could have stayed and competed with Wilson anyway, but he ultimately decided that a fresh start was better for him and his career. He'll get that opportunity in Philadelphia while serving as Jalen Hurts' backup. 

Pickett's time in Pittsburgh also included an awkward position battle with Mitch Trubisky, subpar effort at times from wideouts Diontae Johnson and George Pickens, and teammates openly stating their preference for Mason Rudolph, who signed with the Titans this offseason after the Steelers let him test the market. There were also the conflicting reports regarding whether or not Pickett actually refused to dress for the Steelers' Week 17 game against the Seahawks last season. 

While there were plenty of negatives, Pickett's time with the Steelers included some positives, too. He helped lead the Steelers to a 9-8 finish in 2022 after a 3-7 start. Among the highlights during that span was his game-winning touchdown pass to Pickens on Christmas Eve and his game-winning scoring pass to Najee Harris against the Ravens in Week 17. 

Pickett defeated the Ravens again this season on a game-winning touchdown pass to Pickens. In his second-to-last start with Pittsburgh, Pickett threw for 279 yards while leading the Steelers to a road win over the Bengals

Pickett will now continue his career in Philadelphia while playing for the team he grew up cheering for.