Kenny Pickett’s NFL career is off to a very odd start. The much talked about quarterback while he was in Pittsburgh was traded to the Philadelphia Eagles in the offseason, in a move that aimed for both sides to get a fresh start.

His draft team, the Steelers, were looking for a new direction at quarterback. After two seasons of some late game heroics but overall subpar play at football’s most important position, the team wanted someone new.

Pickett, meanwhile, also didn’t mind a change of scenery. Though he never made a huge public fuss, it was rather clear that he would welcome a move out of Pittsburgh after how things ended last season.

In case you forgot (or don’t regularly follow the Steelers), Pickett entered his sophomore pro season as the undisputed starter for the Steelers. With a dominant preseason behind him, Pickett was destined to improve upon a rookie season that, while rocky overall, ended on a high note.

However, Pickett failed to take the next step. Few touchdown passes and yards per game led to the Steelers resorting to their defense winning them a majority of their games. With Pickett at the helm, the team found wins in spite of him, not because of him.

Pickett still kept the job, though, until an ankle injury chopped him down in Week 13, moving backup veteran Mitch Trubiksy into the starter’s role in Pickett’s absence.

Trubisky, though, was a complete disaster for the Steelers. After three miserable performances and back to back losses to 2-10 teams, Mike Tomlin was forced to go to an option he never expected to have to consider: Mason Rudolph.

Rudolph took over on Christmas Eve Eve and saved the Steelers season. The much maligned quarterback from his time as a starter back in 2019 went 3-0 down the stretch and had given Pittsburgh the best quarterback play they had seen since Ben Roethlisberger.

Rudolph excelled so much that even when Pickett was healthy, Tomlin opted to keep Rudolph in games, including the wild card game that Mason had dragged the team to.

There were also those reports about Pickett refusing to dress as the backup on New Years Eve in Week 17. The truth on that is still hazy depending on where you get your reporting, but that’s not the point of this story.

Either way, by season’s end, Mason’s services had pushed the Steelers and general manager Omar Khan to pursue better quarterback options. The starter’s job was no longer guaranteed to Pickett, he’d have to earn it back.

The situation came to a head when the Steelers signed free agent Russell Wilson to a one year deal. Once Wilson was signed, it seemed pretty clear that Pickett would be resigned to a backup job in Pittsburgh.

Pickett, a former first rounder from two years ago, reportedly was open to moving on, and as it turned out, so were the Steelers. There were reports that Pickett didn’t take kindly to the Steelers drafting Wilson, and that it helped expedite the moving out process. Again, depending on your source of information, that was either confirmed or it wasn’t.

Moving on from a first rounder, especially at quarterback, just two years in would have been unheard of for generations of Steelers fans. But Khan’s Steelers are different. He shipped Pickett off to Philadelphia, along with a fourth round pick, for a third rounder (who ended up being Payton Wilson at 98th overall) and two sevenths in 2025.

Pickett got to suit up for his childhood team, the Eagles, but had to accept a definite backup job to Eagles quarterback Jalen Hurts. It wasn’t a great move for his pro career, having moved out of a place that had signed a veteran to a one year deal and into a place that had an entrenched starter for the long-term future.

Had Pickett wanted to stay in Pittsburgh, there’s a real chance he would have sat a year behind Wilson, perhaps learned a thing or two from a guy who’s been to multiple Super Bowls and had a ring, and then came back new and improved in 2025.

Instead, he appeared to be stuck behind Jalen Hurts, who is signed long term to be the guy for Philly, and is actually younger than Pickett. Kenny’s only option was to be a backup in Philly, if he can even attain that now.

Pickett is reportedly struggling to hold the backup role in training camp. Eagles writers are noting the performance of Tanner McKee, a sixth round selection by the Eagles in 2023.

Eliot Shorr-Parks, an Eagles reporter for Philly’s 94 WIP Sports Radio, is suggesting there’s a real chance that McKee earns the backup job.

This comes on the heels of reporting from Thomas Peterson that says McKee has taken second team reps ahead of Pickett.

Jalen Hurts will be seeing almost no preseason time, so things could shape up to be a real battle for the backup role behind him. Pickett’s job could be in serious danger.

Meanwhile, back in Pittsburgh, a dream position for Pickett would have opened up had he stuck around here.

Russell Wilson started training camp on the sidelines, being held out of reps with a minor calf injury. The Steelers said it was more precaution than anything serious, but the spot allowed backup Justin Fields to come in and give the Steelers’ coaching staff a nice long look at him.

Fields has dominated in training camp, setting himself up to be genuinely considered the Week 1 starter ahead of Wilson, something that was only a dream for those in the Fields-camp a few months ago.

That chance could have belonged to Kenny Pickett. Had Pickett not wanted out, the Steelers would have likely kept him around as the backup to Wilson, and a trade for Fields doesn’t happen.

In that scenario, Pickett would have had the chance to show out in camp and propel himself back into the starter’s conversation.

Now, if he actually would have been able to is a different conversation, one that’s impossible to know for sure.

What can be assured though is that situation in Pittsburgh, with a chance to claim that starter’s role once again, would be a lot more desirable than in Philly, where Pickett now has to scratch and claw to hold onto a backup gig.

If there really is a battle between Pickett and McKee in the preseason, that will be very interesting to keep an eye on for both sides of Pennsylvania.

(Featured photo from Getty Images)