With the Eagles, Kenny Pickett won the ring. With Amy, he won in life. He threw for 267 yards and three touchdowns—a performance few expected, except her. Days before the game, she posted “Super Bowl bound.” After the win, it was “Super Bowl champs.” No big declarations, just belief. It was her constant support that made him say, “I knew when I first started dating Amy that I wanted to marry her.” And yes, they sealed it all with a fairytale wedding in 2023.

Amy Pickett’s been there every step. Long before the trade, long before the Kelly green. A Princeton soccer alum, she’s watched Kenny’s career unfold up close, from college to the NFL. When the Eagles deal went through, she posted it like it was her own: “Could not be more excited and grateful!!” And on Sundays, she was on the sidelines in green, same as always — steady, proud, part of the picture.

So, of course, when hubby’s ex-team celebrated their winning bling, Amy posted a heartfelt three-word message alongside a photo of the Eagles’ Super Bowl ring: “She’s so beautiful.” Then came another post—this time a glowing photo of herself wearing the ring, proud and beaming. Soon after, Kenny posted an Instagram story of Amy proudly flaunting it, a silent tribute to the one who’s always been in his corner. 

And their love story has been as heartwarming as their social media PDA. “We worked out at the same place growing up because Amy played soccer and I played football,” Kenny once shared, hinting at the roots of their connection. They reconnected during a college break in 2021, and from the start, their vibe just clicked. By January 2022, Kenny was ready to make it forever. He proposed with a heartfelt message: “Got tired of calling you my girlfriend…here’s to a lifetime with the person I cherish more than anything.” A love built on friendship, trust, and shared ambition.

Amy is now riding just as hard for her husband in Cleveland as she did in Philly. After the Browns traded for Kenny on March 10, she wasted no time showing support. Her three-word reaction—“That’s my dog”—paired with fire and dog emojis, lit up social media shortly after the move was announced. Later, she doubled down with a video of Kenny at the Browns’ facilities, cheekily captioned “Woof.” From Super Bowl celebrations to new beginnings, Amy remains all in—his biggest hype woman no matter the jersey. But as the confetti settled, a new challenge awaited.

Kenny Pickett enters Browns camp with everything to prove

After a successful chapter in Philadelphia, Kenny Pickett’s time with the Browns is the main talk of the town. With a crowded quarterback room, the competition is heating up. Shedeur Sanders and Dillon Gabriel are in the mix, and tough calls are on the horizon. As CBS Sports’ Jonathan Jones points out, “I don’t see the Cleveland Browns keeping four quarterbacks on their 53-man roster.” That means cuts—or tough demotions—are coming fast.

It’s a numbers game, and Pickett may be the odd man out. According to Jones, the battle between Joe Flacco and Kenny Pickett could decide who stays on the main roster and who’s sent to the practice squad. He explains, “The loser of Joe Flacco vs Kenny Pickett” may not survive final cuts. Complicating things further is Cleveland’s GM Andrew Berry’s strong preference to retain his own draftees: “Andrew Berry, the general manager of the Cleveland Browns, loathes cutting his draft picks.” That alone could tilt the odds against Pickett.

Still, not all hope is lost. On 92.3 The Fan, Bryant McFadden offered a cautiously optimistic take, saying, “Is there any chance Kenny Pickett can be one of those answers? Yeah, he has a shot… I don’t see why not. It’s a wide-open competition.” But even McFadden followed it up with a reality check: “For Kenny Pickett to be able to capitalize on that shot, he has to play better football than he’s ever played in his professional life, in my opinion.” So yes, there’s a path—but it’s narrow, steep, and competitive.