1. Extending Aaron Rodgers instead of trading him in 2022
The time to trade Aaron Rodgers was in 2022. Green Bay had just completed its "Last Dance" season, falling short in a divisional-round loss to the San Francisco 49ers. At best, the Packers could restructure deals and push financial pain into the future just to keep the core of the roster together. Forget adding big-money free agents.
Gutekunst signed Rodgers to a new deal but traded away his top wide receiver just days later. Make it make sense. The Packers needed to go all-in for a Super Bowl or all-out. They did neither.
The Denver Broncos were in the market for a veteran QB, and Rodgers was the reigning back-to-back MVP. They ended up sending two first-round picks, two second-round picks, a fifth-round pick, tight end Noah Fant, defensive lineman Shelby Harris, and quarterback Drew Lock to the Seattle Seahawks for Russell Wilson and a fourth-round pick.
There's every chance the Packers could've landed something similar for Rodgers.
Instead, Green Bay signed Rodgers to a new deal that significantly hurt the salary cap. He stayed for one more season, the Packers went 8-9 and missed the playoffs, then they traded Rodgers to the New York Jets for far less while absorbing a $40 million dead cap hit.
Jordan Love might not have been ready to start in 2022, but the trade would've given the Packers an extra year to evaluate him, which would've been crucial with a decision on the fifth-year option to come.
This season, the Packers would've had more cap space to strengthen the roster without Rodgers' dead cap hit limiting them.
Trading Rodgers in 2022 would've eased the Packers' financial issues, allowing them to strengthen the roster around Love. They would've also added premium draft capital and perhaps even veteran players like the Broncos did with Fant, Harris, and Lock.
In the end, Gutekunst got a good deal for Rodgers, but he missed an opportunity to land so much more.