To make the journey from North Carolina to Lake Forest, Trubisky drove the same beat-up old Toyota car that was once his grandmother's. While he did so partially to fulfill a joking suggestion from general manager Ryan Pace, it also spoke to the Bears of what they were getting in Trubisky. They recognized the kid behind the wheel was more focused on work than flash.
These days, Trubisky is carrying the weight of expectations for a Bears team entering its most anticipated season in years. From coach Matt Nagy to the skill players on offense and so many more inside Halas Hall, the Bears have been built around their great investment in Trubisky.
Quarterbacks live under the microscope, and that's certainly the case for Trubisky, who's now 25. But as critics and pundits outside of the Bears' facility pick away at Trubisky, those closest to him -- the players and coaches who see him every day -- hold an earnest belief in him.
Why do the Bears believe Trubisky can lead them toward their great promise? Take it from their own words.
Few players inside the Bears' locker room know Trubisky better than Whitehair, who was his center for each of the last two seasons before switching to left guard this offseason.
Trubisky has often made light of the bond between a quarterback and center, a reflection of their close relationship. Whitehair has watched the growth of Trubisky as he worked through a difficult rookie season, spent a more successful year of adapting to Nagy's offense and is now managing the pressure that comes with his position.
How does Trubisky handle all of this?
"He's done a great job," Whitehair said. "His leadership has stepped up, his confidence is through the roof right now. We're really happy with where he's at, and he's only going to lead our offense to a great season this year.
"He's going to be great. I know he is. I know the kind of worker he is. He cares so much. He has discipline, he's a great preparer, and I just think he's going to do really well.
"He's just more comfortable, seeing things better and playing at an extremely high level of confidence."
One of the most important parts of Leno's position as the Bears' left tackle is to protect Trubisky's blindside.
On and off the field, Trubisky keeps his focus to football. He removes all social media from his life during the season in order to avoid the outside perceptions. But those like Leno are aware of the constant critics of Trubisky.
Recently, Leno looked over his shoulder after a practice and saw Trubisky running sprints up and down a hill to the side of Field 3 at Halas Hall.
"He knows he's the quarterback of the Chicago Bears and he knows that it's a lot of noise around there," Leno said. "His job is just focusing in on being the best version of Mitch Trubisky. That's his job and that's what he's doing. That's him. Like, it's nothing new. Nobody's changing him, nobody's doing anything, like, that's just him. That's just who he is.
"At the end of the day, (the critics) ... only care about what the results are on the football field. You'll see this year."
Now 39, Ragone was -- and still is -- a fresh face in the coaching industry when he and Trubisky began working together in 2017. Ragone had enjoyed a successful collegiate career at Louisville before bouncing around three NFL teams and even playing a stint with the Berlin Thunder of the NFL Europe.
Ragone's previous work with the Bears made such an impression that he became the lone member of John Fox's offensive coaching staff to be retained by Nagy. His task was to become a mentor for Trubisky.
Now in his third season with Trubisky, Ragone has been there for every snap that Trubisky has taken and throw that he's made. Ragone knows the position of quarterback goes beyond football, and that's where he has seen the strides in Trubisky.
"It's the closed-doors part of it," Ragone said. "It's the growth, the maturation, the mentality in which he takes the position and how he is around his teammates. So, the things that have nothing to do with throwing a slant on time, getting around his guys, demanding a lot from himself but also demanding stuff from his teammates, and then having the presence when he breaks the huddle to see where his eyes are supposed to be. The things that you need as a quarterback to develop long term at this level are the things he's working on, constantly being reminded about and getting better at.
"The way he's gone about it, he understands it's a responsibility -- not just what he does on the field but also how he carries himself off the field. And he takes great pride in that. Which, for someone that age, to be able to understand that already, that just gives me confidence. Now, flip him as a player, he's already understanding how to handle that off the field. Now, he understands how to handle certain situations on the field, and he won't become rattled or distracted from it."
During a rookie season filled with struggles, Trubisky was left throwing to one of the worst receiving corps in the NFL.
The Bears rebuilt their receiver depth ahead of the 2018 season to provide a group of playmakers that could bring Trubisky success. In Allen Robinson, Gabriel and Miller, the Bears added three targets whom they believed could reveal his potential as a passer. Veteran Cordarrelle Patterson was signed this past offseason to bring more versatility into the offense. The team also added an element of speed with Hall, whose fate on the roster will be known this weekend.
In working to establish a rapport with Trubisky, the Bears' receivers have gotten a sense of what makes him click.
"He's such a hard worker and he strives for perfection in everything that he does," Miller said. "He never stops asking questions. He's learning this offense just like we are. It's just his second year in it. I think he's going to be so much better. We all are."
In his first season with the Bears, Gabriel nearly doubled his career-high mark with 66 receptions. He also hauled in 72 percent of targets on the year. He felt part of that success was due to Trubisky's ability to get him open -- which is something that he believes has grown in their second year together.
"A lot of things of just the leverage of the DBs," Gabriel said. "He’s feeling that and also I’m feeling that. I’m not really having to look at him and give him the eye like, ‘Mitch.’ He can feel that already. That just gives us more confidence within each other. It’s a drastic step from coming in here last year."
One of the newer additions to the Chicago offense, Hall was signed in March after two seasons in Atlanta alongside Matt Ryan. How Trubisky leads caught Hall's attention quickly.
"I love Mitch," Hall said. "Mitch is a great quarterback. He's very vocal. He's always on edge as far as wanting to be perfect. I love it.
"It shows that he can lead. First and foremost, that's what you want as a quarterback, a leader -- somebody that can take charge and get everything accomplished that needs to be done."
The Bears hired Nagy as their head coach in January 2018 in part because of their belief in what he could mean to Trubisky's potential. Less than a year removed from Pace making Trubisky the second overall pick in the draft, he hired a coach who could cater to that quarterback.
Nagy has constructed an offense around Trubisky, ascended from level 101 now to 202 with him in the understanding of the offense and established the kind of coach-quarterback dynamic that many peers around the league envy. Nagy has praised the growth of Trubisky while downplaying the mistakes that have come.
Nobody has spoken about Trubisky the quarterback more than Nagy. So, after the Bears' preseason finale at Soldier Field on Thursday, he answered one last Trubisky question before they embarked on this revealing season together.
Where's Nagy's confidence in Trubisky entering this pivotal season?
"I feel really, really good with where he's at," Nagy said. "I know he's worked really hard. Even just this past week, for us being able to see in meetings to see where he's grown from, I think about last year to this year where he was at and the questions he's asking me and the questions he's asking Rags and (offensive coordinator Mark) Helfrich.
"I have ultimate confidence in where he's at. I'm excited to see what this year is going to bring for him."