On December 3rd, 1985, the Chicago Bears were fresh off of a defeat at the hands of the Miami Dolphins in what was one of the most highly anticipated Monday Night Football matchups in the history of the NFL. The Dolphins were the reigning AFC Champions, and the Bears entered the game with a perfect 12-0 record, with their sights set on becoming the first time to finish the regular season with a perfect record since the Dolphins did so 13 years prior. Miami would win 38-24, preserving the 1972 team's distinction as the only team to complete a perfect season during the Super Bowl era.

It was the type of loss that today's sports media cycle would've turned into an absolute feeding frenzy, with countless talking heads questioning whether or not the Bears were “for real.” But inside of the Chicago locker room, a loss in Miami didn't exactly register as a panic-worthy result. In fact, the team was so calm that they stayed in Miami an extra day in order to both film and record the now iconic “Super Bowl Shuffle,” a made-for-MTV crossover hip-hop hit that all but guaranteed that the '85 Bears would soon be capturing the franchise's first NFL title since 1963.

Just 75 days before Walter Payton, Mike Singletary, Jim McMahon, Willie Gault and the rest of the Bears Shufflin' Crew would strut their stuff for everyone, Canandaigua, New York couple Robert and Mary Ellen Poles brought their son Ryan into the world.

Ryan Poles would go on to be a standout athlete in high school, a starter on the offensive line at Boston College, a fast-rising front office prodigy in Kansas City learning under the likes of John Dorsey, Scott Pioli, Chris Ballard, Brett Veach and Andy Reid, and now, just a little over 38 years after the Bears one and only Super Bowl victory, the man who has helped lead the franchise to the precipice of glory once again.

When Ryan Poles was hired as the General Manager of the Chicago Bears in January 2022, his stated goals were lofty, but also pretty straightforward, according to Adam Jahns of The Athletic.

“I just want to be successful. I just want the organization to be successful and be at a championship level. I want to be a championship GM,” Poles said.

Now you could say that this was nothing more than typical new General Manager speak, and that may be true, but before the Bears could realistically dream of reaching that point as an organization, Ryan Poles would have his work cut out for him.

For the better part of my life, the Bears have been a punchline of sorts. They've become synonymous with poor coaching, offensive ineptitude, and subpar ownership and management. The '85 Bears won a Super Bowl title six years before I was born, so myself and other Bears fans who are Millennials or younger have no clue what sustained excellence in the Windy City looks like. In fact, since 1992, the Bears have made the NFL Playoffs in consecutive seasons only once, an embarrassing mark for any franchise, let alone the one in the third biggest media market in the country. So not only would Ryan Poles need to deal with all of the emotional and karmic baggage that came with the job, but he had one hell of a rebuild ahead of him.

Poles was inheriting an old and expensive team that had maxed out as a fringe postseason contender at best, though many Bears fans — myself included — would argue that the 2018 squad should've advanced beyond the Wild Card Round. Even still, Poles was not walking into a win-now situation, as very few general managers do. But this rebuild in particular would not be easy. It would take two long years of patience, precision, difficult decisions, criticism, luck, and some remarkable foresight before the Bears could get to where they are right now… on the verge of turning the tides and hopefully becoming what they once were, which is one of the best franchises in the NFL.

To do so, Ryan Poles and the Bears needed to make a lot of tough decisions along the way. In less than one year's time, Poles would smartly opt to trade away Khalil Mack, Robert Quinn and Roquan Smith, arguably three of the best players on the entire roster, in order to shed salary and acquire draft assets. The Roquan Smith trade was particularly hard for Bears fans to swallow, given how dominant Smith had been in just a few short years in Chicago. He looked the part of the next great Bears linebacker, but Ryan Poles wouldn't budge during contract extension negotiations, and Smith was sent packing.

The name of the game was accumulating draft picks and clearing cap space, and it wouldn't be long until the Bears would find themselves with plenty of both. But of course, draft picks and cap space don't guarantee a successful rebuild.

It's all about what you do with those picks and that cap space, but the fact that Poles had to do so much work just to give the Bears the opportunity to rebuild should be considered when evaluating his job performance, as should the fact that he didn't have a 1st round pick to work with in his first draft as the GM of the Bears, because previous GM Ryan Pace gave it up in a draft night trade in 2021 to move up in order to pick Justin Fields. Even still, in the last two drafts, the Bears have made 21 picks and found what will likely be six starters on opening Sunday of the 2024 NFL season — Kyler Gordon (2nd round), Jaquan Brisker (2nd round), Braxton Jones (5th round), Darnell Wright (1st round), Tyrique Stevenson (2nd round) and Gervon Dexter (2nd round).

To this point, however, it's fair to say that Poles' legacy as the Bears general manager has been defined by the one pick he didn't make.

Bears, Ryan Poles

Thanks to a Houston Texans victory on the final Sunday of the 2022 regular season, the Bears would enter the 2023 offseason with the number one overall pick in the NFL Draft. Lesser general managers would've been quick to either trade Justin Fields, the beloved yet enigmatic QB1 of the Bears whose NFL future was very much still up in the air, or quick to trade the pick. Fortunately for the Bears, they didn't hire a lesser general manager in January 2022.

“Maybe he’s churning up inside, but he exudes calm,” Bears chairman George McCaskey said of Ryan Poles recently, per Kevin Fishbain of The Athletic. “And I think that’s very helpful for his staff, especially, but for the entire building to see the leader of our football operation taking thoughtful, measured steps to make us better.”

In high pressure situations like the ones Ryan Poles faces every day, taking “thoughtful, measured steps,” is not always easy. But that's exactly how Poles handled trade talks with teams leading up to the 2023 NFL Draft, thanks in part to regular meetings with a sports psychologist.

“The biggest thing is just kind of quieting my mind,” Poles told Kevin Fishbain. “Which is tough because part of what I think helps me do a pretty good job is you’re always going through all these different scenarios in your mind. If this doesn’t work, if this doesn’t work, we’re going to go to the next thing and the next thing. You always have these like four different, five different layers, but you’re always constantly sitting there dwelling on what could go wrong. And I think that can be a very stressful place to be. So managing that’s probably the biggest thing.”

Finally, a month and a half ahead of draft night, after weeks of trade talks with teams all around the league, the right deal finally materialized, and that was when Ryan Poles pounced. As a result of the deal with the Carolina Panthers, who selected Alabama quarterback Bryce Young with the pick, the Bears have since turned that #1 pick that Poles didn't make into the following: DJ Moore, Keenan Allen, Tyrique Stevenson, Darnell Wright, a 2025 2nd Round pick, and yes, Caleb Williams.

So here is where we stand right now: If Caleb Williams ends up being the guy in Chicago — and I'll concede that, given the Bears tortured history with quarterbacks, this is a big if — it will be in large because Poles positioned the Bears not only to be able to take Williams, but to help him succeed. Caleb Williams will be stepping into an offense with two bonafide #1 receivers, a 1,000-yard rusher who is leading a strong stable of running backs, an offensive line that should be better than we've seen in Chicago in years, and a defense that was among the best in the league during the second half of last season, with arguably its two best players (Montez Sweat and Jaylon Johnson) returning on four-year extensions.

“We’re proud of where we’ve come from,” Poles told reporters Tuesday, per Alyssa Barbieri of USA Today, and let me be among the first to say, he damn sure should be proud. This has been a masterclass in modern NFL team building, and it's been done in just two years time, even though never once has it felt like the process was being rushed.

Now comes the fun part. Bears fans get to watch how all of this plays out. And while the old saying goes, “The best laid plans of mice and men often go awry,” it's nice to know we've got a GM who is actually capable of carrying out some franchise-defining plans.

And for that and that alone, let's give Ryan Poles his goddamn flowers.