The opportunity to work with a close friend in Bears coach Matt Nagy within an easy drive from his family's roots in Aurora was something Childress viewed as special. It was something different than any other offer that he could've received.
"It's Matt," Childress said. "I love Matt as a person. I probably wouldn't do it with anybody else besides Matt. And, No. 2, I'm a lifelong Chicago Bears fans.
"It's natural to come back here and be with my family ... It's perfect."
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After spending part of 2018 as a consultant with the Bears, Childress was officially hired as a senior offensive assistant on Nagy's staff in early May. From a technical standpoint, Childress will help create practice scripts and game plan during the season.
But what Nagy really appreciates is having a trusted ally as a sounding board amid everything an NFL season can throw at a head coach.
"He’s not scared to tell me when I’m doing something maybe wrong or when I maybe should think about doing something else," Nagy said. "He’ll give me advice. He’s not worried about who I am or what I do or what my title is.
"I love that. It keeps you where you need to be. From the day I met him, I’ve always felt that way about him, so he helps me.”
Having been the Vikings' head coach from 2006-'10, Childress respects the way Nagy seeks other voices in leading the team.
"I'm never short of an opinion, and he wouldn't ask if he didn't want one," Childress said. "I don't have any trouble saying anything to him. He doesn't have any trouble saying anything to me. There's a very clear line of communication. It's refreshing sometimes."
A native of Aurora and graduate of Marmion Academy, Childress grew up watching the Bears. He and his father, now 88, attended Bears games at Wrigley Field, watching the greats like Gale Sayers run through defenses. As a kid, Childress even attended the Bobby Douglass football camp at Marmion. His wife, parents and in-laws still call Aurora home.
After coaching his first 20 years in the college ranks, Childress shifted to the professional game in 1999 as quarterbacks coach for Andy Reid's Eagles. He served as offensive coordinator beginning in 2002 and helped Philadelphia reach the Super Bowl in 2004. Two years later, he was named head coach of the Vikings.
Childress led Minnesota to consecutive NFC North titles in 2008 and 2009 but was dismissed 10 games into the 2010 season. After spending 2012 in Cleveland, he reunited with Reid in Kansas City and joined an offensive coaching staff that included a rising assistant in Nagy.
That's where their friendship began.
"We have a lot of laughs," Childress said. "He can poke fun at himself, I certainly can poke fun at myself. We don't take ourselves too seriously. But at the same time, there's an understanding, a standard that he wants, whether it's how you write a seven-on-seven script, a team script, how he wants things laid out. I get that where he's coming from, how he wants it, and I'm able to do that for him and still enjoy what I'm doing, interact with the players, the coaches, and interact with him."
Added Nagy: "Everybody here knows how well we get along and how much I look to him for advice."
Childress left his role with the Bears last season to become head coach of the Atlanta franchise in the Alliance of American Football. However, he resigned from the position in early January, one month before the season began.
The AAF would shut down operations in early April after its funding dried. Childress sensed "something was amiss" with the league before it even played a game.
"I would just say that it wasn't right," Childress said. "I thought it was going to be great. I thought it was going to be with people that were football oriented, with Bill Polian's name on it. The bones and the structure being good football people. But if you don't have the money to run the organization ... Probably the thing that I learned most doing this 40 years is if there's something that doesn't feel right, and your gut's telling you it doesn't feel right -- and I have a rather ample gut -- trust your gut."
Childress enjoyed watching the Bears go from worst to first in the NFC North under Nagy's watch last season. He would call Nagy after every game, speaking to him as the team boarded its charter or as Nagy drove home with his family from Soldier Field.
Childress enjoyed watching games as a fan on the couch, often cursing at the television like a coach on the sidelines. What he didn't miss was seeing the Bears' heartbreaking end to the season in their playoff defeat to the Eagles.
In the end, Childress felt an immense pride for what made Nagy successful.
"I'm happy as I could be for him."