Their paths diverged on April 27, 2017, as they knew they would.

Bolles, Trubisky and 20 other top prospects in the 2017 NFL Draft were gathered in the green room for the first night of the draft at the Philadelphia Museum of Art, waiting anxiously with family and friends.

Each young man had a table each with about eight extra seats for people they wanted to invite. Bolles' table was filled out by his adopted parents, Emily and Greg Freeman; his birth father, Grove; a couple of Garett's coaches from the University of Utah; his wife, Natalie; her parents; and, of course, Garett and Natlie's infant son, Kingston.

And just a table away was Trubisky and his family.

It was just fitting that even on that night, they wouldn't be far from each other. After all, they were side by side for the training process that led them to this point.

"We trained together, me and Mitch Trubisky, and ever since the day we saw each other down in training, we just became really close friends," Bolles says.

The two had the same agent at REP1, but more than that, it was the kind of youthful, instantaneous friendship that just seems to be natural, and as they trained, they tried to help one another become even better football players.

"[Were they] connected? Yup," Emily Freeman says. "From the very beginning, Garett and Mitch were in that same class coming in — and I don't know if you've talked a lot to Garett, but he is very passionate about protecting quarterbacks. So that is how that relationship began. It's just with that — with Garett just wanting this intense protection for a quarterback in the family. They would spend a lot of time together. … Before the draft happened, [it would be] Mitch talking to Garett about protection and what that looked like, and Garett also talking to Mitch, both of them just helping try to improve each other, clear back before any of them were in the NFL."

Back on draft night, they and their families sat at their tables, waiting not quite in silence but waiting anxiously all the same. The food provided for the room sat mostly untouched, Bolles recalls — everyone was too nervous to eat.

"You're sitting there at the table waiting to hear [your name]," Bolles says.

Trubisky, as a top quarterback prospect, would get the call first of the two. But there was little consensus on his destination before the Bears made the trade up to No. 2 that night. Mock drafts put Cleveland as the most likely destination — but at the 12th-overall pick, not first overall. So when Chicago made their move to draft Trubisky, many viewers and analysts were surprised.

But the Bolles family wasn't.

"I knew he was going to go high," Bolles says. "I knew he was the best quarterback in the draft — 100 percent, I knew. I saw it: the way he worked, the way he held himself, what he had to do. And him going to Chicago was perfect."

Emily Freeman knew it, too.

"We came in knowing that Mitch was going to go in one of those top two spots," she says. "As we came in and we watched, we almost set aside what we were waiting for and what we were hoping for, just to be able to support and celebrate the Trubisky family as they were going through that process. Watching them go through that and just the joy on their family's faces as they celebrated that. But I also will never forget going over once he had hugged his mom and his dad and they were walking around that table and I turned around and Mitch's mom changed it up, but we just gave each other a big hug."

"That was another big thing," Bolles says, "knowing he got drafted and saw how excited I was to see him go No. 2 overall and how happy I saw his mom and his dad and his brothers. I was so excited for them."

Bolles' own selection didn't have the same drama, but the reception from the Trubiskys was the same, as they and other REP1 clients and families joined together for a celebratory dinner after the first night of the draft concluded.

"Being there in Philadelphia on a special night with our families, it was awesome," Bolles says. "My family is really close to his, and his family is really close to mine. And that's how it's always going to be."

Freeman, who was seated across the table from Jeanne Trubisky, felt the same way. Though their sons had just joined the NFL that night, Freeman knew that the bond they shared and this jubilant night they shared as mothers would be something she'd treasure forever.