If Bears thrive, expect assistant GM Ian Cunningham to be running his own team next year (2024)

LAKE FOREST, Ill. — Ian Cunningham is on the cusp of achieving a lifelong goal.

The Chicago Bears assistant general manager has been viewed as a rising executive among his peers around the NFL, and he’s got the receipts to show for it. Cunningham has interviewed in recent years for general manager vacancies with the Arizona Cardinals, Tennessee Titans and Los Angeles Chargers.

Now if the Bears’ season plays out the way many expect — an offseason acquisition spree has generated as much hype as ever in Chicago — Cunningham will again be on the shortlist for teams with GM openings in January.

“It feels great in the sense of this is what I’ve worked for my entire life and career,” Cunningham told The Athletic. “Knowing what I’ve wanted to do since I was in middle school, high school and setting that goal for myself. … Realizing I’m on the cusp of that, I’m extremely fortunate to have the interviews in which I’ve had and the opportunities in which I’ve had. I just view it as just keep chopping, and it’ll happen in the right time.”

Cunningham’s peers’ eyes light up when his name is mentioned, whether it’s someone he’s worked alongside or against. Executive circles are tight, so it’s paramount to build trust, and it’s clear Cunningham has established that.

He’s also cut his teeth with two of the NFL’s premier front offices, first breaking into the business from 2008-16 in personnel and scouting roles with the Baltimore Ravens and then from 2017-21 in director roles with the Philadelphia Eagles. Cunningham joined general manager Ryan Poles with the Bears in 2022.

It’s been an impressive ascension, but Cunningham has been chasing this goal since middle school — or at least until he determined the front office route was more ideal than trying to become a color commentator in the broadcast booth. Cunningham kept the latter possibility open as he worked on air at WINA during his time at the University of Virginia.

“As time went on, I was always fascinated by team building, roster construction,” Cunningham said.

Cunningham, a starting guard and center at Virginia, signed with the Kansas City Chiefs as an undrafted free agent in 2008. But he was realistic about his future.

“I quickly realized I wasn’t going to be there long,” Cunningham said. “I wasn’t good enough, just wasn’t strong enough. Once I got released, I knew, hey, I’m not going to chase the carrot. I’m not going to go on the workout circuit. I wanted to get into personnel.”

That’s when Cunningham’s college coach, Al Groh, went to work on his behalf. Groh spent more than a decade in the NFL, including an overlap with Ozzie Newsome in 1992 with the Cleveland Browns, so he reached out to his network to try to get Cunningham in the door.

Within 24 hours, Cunningham had an interview lined up for Newsome’s personnel internship with the Ravens. As it turned out, Newsome was looking for a like-minded 20-something who was willing to grind to make it in the executive world.

“I felt Ian was Ozzie’s kind of guy,” Groh said. “I was very comfortable calling up Ozzie and telling him, ‘Hey, you’re going to like this guy. He’s smart. He’s tough-minded. He’s a real football guy. He deals well with people, but he knows football, and he knows what kinds of players will play good football.’ He had the intellect and the people skills to be successful in an executive position in any career path he chose.”

Under the guidance of a legendary general manager like Newsome and his eventual successor, Eric DeCosta, Cunningham learned consistency, discipline and conviction to only worry about what’s inside their building. Naturally, they studied other teams’ processes, but the Ravens have sustained a high level of success for so long because they remained committed to their ideologies.

It also helped that Cunningham could watch the likes of future Hall of Famers Ed Reed and Ray Lewis along with greats such as Terrell Suggs, Anquan Boldin and Matt Birk. Cunningham had a front-row seat to greatness, and he used that to his advantage when he went on scouting assignments. He knew what he was looking for, so he grew confident in his questions.

“They speak the same language. They know what they’re looking for,” Cunningham said of the Ravens. “Growing up in that building, you learn how to evaluate. You learn how to scout — what plays in the league, what doesn’t play in the league.”

Ryan Poles 𝙡𝙤𝙫𝙚𝙨 this Bears team.

"I've never been around a group like this."

More from Poles, with @Adamjahns and @AdamHoge, on Caleb Williams and all things Chicago ⤵️https://t.co/cZbyfXOO4N pic.twitter.com/t66wYypnaf

— The Athletic (@TheAthletic) August 20, 2024

With the Eagles, who are uniquely analytically driven, Cunningham could blend his football knowledge with a different way to view roster construction under general manager Howie Roseman. There’s a reason why disciples of DeCosta and Roseman are among the most coveted during modern hiring cycles.

“I had the foundation of evaluation (with the Ravens), and (with the Eagles) I got to mix in the data and analytics to see how that meshes and what I can make in that pot of creativity, so I’m blessed in that sense,” Cunningham said. “I get to go to Baltimore and learn from who I believe is the best GM in the history of the NFL in Ozzie, and learn from Eric DeCosta, who in my mind is a top-five GM, and then get to learn from Howie Roseman who is another top-five GM. So I’ve got to pinch myself at times because of how fortunate I’ve been.”

Cunningham will likely be a hot name during the next cycle regardless of how the season plays out. But realistically, a Bears playoff berth would immeasurably strengthen his candidacy.

Poles and Cunningham took over a reeling franchise in 2022. The Bears had just hired head coach Matt Eberflus to replace Matt Nagy, and the roster was devoid of talent and hindered by questionable salary cap decisions. They recognized a rebuild that required a great deal of patience.

Their approach was methodical. They needed to evaluate whether quarterback Justin Fields could be a franchise cornerstone, which gave them the freedom to trade away the No. 1 pick in the 2023 NFL Draft to the Carolina Panthers. Among the haul, the Bears recouped star receiver D.J. Moore and the No. 1 pick in 2024 that turned into quarterback Caleb Williams.

They’ve also added pass rusher Montez Sweat and linebacker Tremaine Edmunds to Eberflus’ improving defense — they very nearly acquired Matthew Judon from the Patriots last week — and patched up the relationship with cornerback Jaylon Johnson, keeping him on a long-term deal rather than trading him away. On offense, the Bears fortified their skill group by drafting wideout Rome Odunze, trading for receiver Keenan Allen, signing tight end Gerald Everett to complement Cole Kmet and adding running back D’Andre Swift.

The bar had been so low for so long in Chicago that such stark progress has been easy to notice. The Bears have had a top-20 scoring offense twice in the past decade, and they’ve only made two playoff appearances since their last postseason victory in 2010. Their quest for a franchise quarterback has led to one error after another.

They appear to be on the verge of breaking through, though questions remain with the offensive line and the NFC North is on an upward trajectory. Success can never be assumed.

But if it’s achieved?

“I feel like we’re on the right track to building a championship culture here,” Cunningham said.

And the league has taken notice of Cunningham’s part in the process. If the Bears thrive in 2024, Cunningham may have the keys to his own front office in short order.

(Photo: Brian Cassella / Chicago Tribune via Getty Images)

Jeff Howe is the NFL National Insider for The Athletic. A native of Lowell, Mass., and a UMass graduate, he previously covered the New England Patriots from 2009-21. Howe, who has been with The Athletic since 2018, is the author of “If These Walls Could Talk: New England Patriots.” Follow Jeff on Twitter @jeffphowe