It’s a lot easier to be a GM in the NFL when you’re getting solid QB play but aren’t having to pay $20M against the salary cap to do it. When you can instead spend that money on, for example, a Hall of Fame caliber OLB while still getting good play from your QB, it makes it so much easier to fill out a team.
Look at the NFL over the last decade plus.
When the Panthers went 15-1 and lost the Super Bowl, Cam Newton was on his rookie contract. They haven’t been back since.
When the Seahawks went to back to back Super Bowls, Russell Wilson was on his rookie contract. They haven’t been back since.
The Ravens won their last Super Bowl with Flacco on his rookie contract. He signed that huge extension and they’ve been to the playoffs once since.
After Aaron Rodgers’ first year as a starter, he signed a relatively modest extension at around $10M a year. The Packers won a Super Bowl. They haven’t been back since he signed his next extension at over $20M per year despite arguably playing better than any QB ever has during that time.
Similarly, coming off a severe shoulder injury, Drew Brees signed a relatively modest contract with the Saints at about $10M per year. They won their Super Bowl. They haven’t been back since signing his first big extension despite breaking pretty much every record a QB can break over that time.
The Steelers won two Super Bowls when Rothlisberger was on his rookie contract and haven’t won since.
The Patriots are the exception that proves the rule, and have been notoriously ruthless with their salary cap, often cutting beloved veterans, while Tom Brady has repeatedly extended for less than market value. (I’m convinced there’s a partial ownership deal under the table.)
Point I’m making is that Trubisky looks like he can be that guy. So the Bears need to make hay these next three or four years before he gets his first big contract.