Trubisky saw the Bears on the brink of a run toward the Super Bowl in 2019 and believed he would be the one leading that charge.
"I'm nowhere close to where I want to be, but I think I'm on the right path," Trubisky said in an interview early last May. "That's encouraging. But I always tell myself the sky's the limit. Don't put any limitations on what you can accomplish or how good you can be. I feel like I'm just scratching the surface."
The 25-year-old Trubisky didn't reach the new heights that he anticipated this season. He took a major step back in his third season, completing just 63.2 percent of his passes for 3,138 yards, 17 touchdowns and 10 interceptions. Trubisky ranked 32nd -- dead last among all qualified quarterbacks -- with 6.1 yards per pass attempt.
After going 12-4 and winning the NFC North in 2018, the Bears went 8-8 and were eliminated from playoff contention with two weeks remaining in a lost season. Trubisky hoped to be the reason why the Bears would win big in 2019, so he understood the team's disappointing season in large part fell on him.
"I got a lot of personal drive and fire within me that I know I haven't played to my potential yet," Trubisky said before a season finale that proved to be meaningless. "I think that's frustrating, but it's also something that motivates me a lot."
This offseason gives Trubisky the chance to reset for 2020, but he's left wondering whether the Bears will offer him another chance as their starting quarterback.
While scouting the Sun Bowl in late December 2016, Bears general manager Ryan Pace gained another impression of what he believed would be a franchise quarterback. That was Trubisky, who nearly led North Carolina to a comeback over Stanford.
Days later, Pace offered support for then-coach John Fox, who led the Bears to a 3-13 mark in his second season in Chicago. From there, Pace and the Bears began making missteps that ultimately jeopardized the growth of Trubisky.
While the Bears were preparing to use their first-round pick on a quarterback, they declined to make a coaching change that would best suit that player with the necessary structure. Fox and his staff were also left in the dark regarding Pace's plans at the quarterback position until the last minute. When the Bears drafted Trubisky, it became more clear Fox was a lame duck and the head coach who would be most influential on Trubisky wasn't in Chicago yet.
"The most important position in all of sports is quarterback, and I don’t think you’re ever a great team until you address the position and you address it right," Pace said after selecting Trubisky.
Trubisky took over as the starting quarterback for the struggling Mike Glennon in the fifth game of the 2017 season. Trubisky did so with a poor receiving group and an antiquated offensive system that didn't put him in a position to have success.
That was in contrast to the situations encountered by the next two quarterbacks selected in the 2017 draft class.
The Chiefs traded up to select Patrick Mahomes with the 10th pick and essentially redshirted him for a season, letting him develop as a backup while learning from coach Andy Reid and then-offensive coordinator Matt Nagy. He emerged as the league MVP a year later in 2018.
The Texans took Deshaun Watson 12th overall and quickly positioned him as their starter in an offense built to his strengths. He had immediate success before suffering an ACL tear in November of his rookie season. He has since earned Pro Bowl honors in both 2018 and 2019.
The Bears had no defined plan for when Trubisky would take over as the starter, and management understood that he'd likely be learning an entirely new offensive system a year later. That process began when Nagy was hired as coach in January 2018, just more than a week after Trubisky's uneven rookie season ended.
Nagy brought with him former Oregon coach Mark Helfrich as offensive coordinator, retained Dave Ragone from Fox's staff as quarterbacks coach and invited in former Vikings coach and mentor Brad Childress as a consultant. The Bears signed veterans Chase Daniel and Tyler Bray as backup quarterbacks, roles that would also include tutoring Trubisky.
Nagy believed his offense and support system would reveal the best of Trubisky.
"All the other stuff, that will come," Nagy said during his introductory press conference.
After two years working with Nagy and three seasons leading the Bears, Trubisky hasn't materialized as the team once believed.
When Mahomes and the Chiefs battle Watson and the Texas in the divisional round on Sunday, it will bring yet another opportunity to relive the 2017 draft.
Would the fate of the Bears' quarterback decision of 2017 be different if they provided Trubisky with the continuity, structure and support that Mahomes and Watson have enjoyed? Would Mahomes and Watson have become NFL stars so soon if they had received the hand that Trubisky was dealt?
Many variables have affected the course of the three franchises since that draft night, but the 2019 season brought Trubisky a fair proving ground against his quarterback peers. He fell far short of them.
The Bears offered unwavering support of Trubisky during a year that spiraled away from them. A day after the Bears lost their much-anticipated season opener 10-3 to the Packers on Sept. 5, safety Eddie Jackson chastised fans who had booed the team in the loss -- then applied that point specifically to Trubisky.
"Your quarterback, he needs the confidence," Jackson said on 670 The Score. "You got to build him up, let him know, 'We're still rocking with you.'"
A week after that game, Trubisky conducted his regular media availability at Halas Hall and informed reporters he "was told not to talk about the last game." The Bears relentlessly protected the psyche of their quarterback, perhaps to a fault.
Did the Bears overload Trubisky?
"That's a real question because sometimes it can be complete paralysis by analysis if you get too much of that," Nagy said in November. "We're not at that point, because we have a control of it in the building. We have a method to how we go about handling him."
That's one of many factors Nagy and the Bears must examine this offseason in assessing whether Trubisky should be the team's quarterback in 2020. The Bears lost control of Trubisky's confidence, Nagy's scheme proved to be a poor fit and other than Allen Robinson, the supporting cast on offense did its quarterback no favors.
Trubisky is careful with his words when speaking to the media, but he often seemed hinting at frustration with Nagy's system. Trubisky's best stretch of games came late in the season, as the Bears catered to his mobility by changing his landmarks, incorporating more play-action and operating with a greater tempo. After a win against the Giants on Nov. 24, Trubisky referred to that as a "strength" for the offense as a whole.
Then Nagy went away from that during a loss to the Packers on Dec. 15, a day that saw the Bears' playoff hopes get extinguished.
"I thought we could have taken more pressure off (the offensive line) moving the pocket a little more and getting me out," Trubisky said after that game.
"We just got to continue to find ways to take pressure off our O-line with a good pass rush like that -- continue to mix it up, whether it's screens, running it, draws, all that kind of stuff that helps.
"Could have done a lot of stuff, yeah."
Nagy, Pace and the Bears must address the quarterback position with a simple premise: Are they better suited with an offense built for Trubisky or a quarterback who best fits Nagy's preferred system?
The disconnect between Trubisky and Nagy set back the offense and team back in 2019.
Since joining the Bears, Trubisky has shut down his social media during the season. He attempts to avoid the outside discussion and criticism, though he has been aware of the perception of him.
"There are no do-overs," Trubisky said late in the season.
Pace indicated the Bears may not retain Daniel and Bray as their backup quarterbacks, which leaves them with spots to fill on the depth chart. Come March 18 and the start of NFL free agency, the Bears could sign a quarterback whom Pace views as serious competition for Trubisky.
The jury isn't out on Trubisky's fate. He has been inconsistent at best during three seasons in the NFL and hasn't elevated the Bears. Perhaps there's a better play in Trubisky if he and the Bears come back confident and better prepared in 2020.
Trubisky's first task of this long offseason will be to clear his head of 2019 -- the hope it once held, the frustration of losing, the burden of a now-disheartened franchise -- and move forward.
And the Bears must find whether they can still do right by their quarterback.