Column: As Chicago Bears owner Virginia McCaskey turns 100, her pride and optimism still resonate

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The first thing that became obvious was Virginia McCaskey’s ebullience, the way she entered the room with infectious pep. On a Sunday afternoon in Phoenix in March 2019, McCaskey had come to do something she hadn’t done at any point in her 96 years. As she walked into a dining room at the Arizona Biltmore before the NFL spring meetings, she was entering the realm of podcast guest.

“This,” she said, “is a first for me.”

McCaskey, the Chicago Bears owner, had agreed to sit down with the Tribune’s “Bear Download” podcast to help kick off the 100th-season celebration for the Bears and the NFL. And while she wasn’t sure where that conversation might steer, she did know that at a landmark time in the history of the league and the franchise her father George Halas founded, she had been lucky.

“It’s not so much a matter of pride as it is gratitude,” she said, “for all the good things that have happened to the National Football League and for the Chicago Bears in all this time.”

If McCaskey’s eagerness and energy delivered an immediate impression, her razor-sharp memory fueled the conversation, offering encyclopedic detail on a time-machine blast through a century of professional football memories for one of the NFL’s charter franchises.

McCaskey not only remembered the league’s 1932 de facto championship in an add-on game played indoors at Chicago Stadium for economic reasons — Bears 9, Portsmouth Spartans 0 — she remembered the tickle it put in her nose. “Just the odor,” she said. “It was almost overwhelming. Because the circus had just left town.”

McCaskey not only cherished the Bears’ 1940 championship triumph over Washington but remembered taking the train as a student at Drexel University from Philadelphia to Washington to see the Bears take an opponent they had lost to 7-3 three weeks earlier and trounce them 73-0.

She spoke glowingly of the relationships she built over time with players such as Brian Piccolo, Walter Payton and Brian Urlacher. And she gushed about the confidence Buddy Ryan instilled in the most fearsome defense the sport might have ever seen, the 1985 bunch that propelled the team’s only Super Bowl-winning journey.

“Buddy just seemed invincible,” she said. “I’ll always remember those scoreless playoff wins. How often does that happen? It was beautiful.”

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[ [Don’t miss] Virginia McCaskey rarely does interviews, but she sat down to talk about the Chicago Bears’ 100th season. Listen to the podcast here. ]

McCaskey turns 100 years old Thursday, a milestone birthday for the Bears owner. And her passion for the team has not dissipated. Matt Eberflus recalled Wednesday the first phone conversation he had with McCaskey a little less than a year ago when he became the organization’s 18th head coach with an important blessing.

“She said, ‘Matt, you know I’ll be your biggest fan,’ ” Eberflus said. “(She is) always encouraging, always upbeat, always thoughtful. It’s been a joy to get to know her this last year.”

That’s a sentiment shared by so many who have crossed McCaskey’s path and come to recognize her competitiveness, belief and charm.

It goes without saying that McCaskey probably hasn’t been thrilled with this season’s shortcomings during a dismal last-place season in which the Bears are stuck in a franchise-record losing streak of nine games and counting — even with the highlight-reel moments that have come from promising second-year quarterback Justin Fields.

The season will finish Sunday at Soldier Field against the Minnesota Vikings and the Bears will have to turn their attention quickly to a demanding offseason overseen by general manager Ryan Poles.

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Nine years ago at this time, after a Phil Emery- and Marc Trestman-led Bears team went 5-11 and experienced four-plus months of dizzying dysfunction, McCaskey’s son George, the team chairman, famously relayed his mom’s pronounced agitation.

“She’s pissed off,” George said the day the team fired Emery and Trestman. “I can’t think of a 91-year-old woman (for which) that description would apply. But in this case, I can’t think of a more accurate description. She’s been on this Earth for eight of the Bears’ nine championships and she wants more. She feels it’s been too long since the last one. … She’s fed up with mediocrity. She feels that she and Bears fans everywhere deserve better.”

That fed-up feeling has been shared and all too familiar for a fan base that in the 30 seasons since the Mike Ditka era have watched the Bears experience 11 last-place finishes and only four playoff victories. Such a prolonged stretch of struggle only amplifies the frequent criticism of a sputtering organization and those who run it.

In March 2019, though, as the Bears headed for their 100th season, McCaskey shared the belief of most fans that the Bears were on the verge of something better. The 2018 team — with All-Pro Khalil Mack igniting a menacing defense and Matt Nagy earning Coach of the Year honors — won the NFC North and seemed to open their window to becoming annual championship contenders.

In Week 1 of 2018, McCaskey was invited to speak to the entire team at the George “Mugs” Halas Auditorium at team headquarters. And her pep talk — centered around confidence, delivered with maximum charisma and referencing the ‘85 Bears — resonated with a group that went on to win the division with the league’s best defense.

“She said the ‘85 Bears were so cocky that it scared her,” linebacker Danny Trevathan said. “That message was received.”

Added Akiem Hicks: “She is very energetic and so very passionate about the things she says. So there was definitely full attention in the room.”

If only that 2018 success had become a runway for a grander flight.

The 1985 Bears remain the most celebrated and iconic group from the team’s 103-year history, a group that surprised even McCaskey with the heights they reached.

“It’s kind of a wonder they even operated as a team,” she said with a laugh. “Because there were so many different kinds of people and characters. It seemed like there were always different things happening and they were going in different directions. Yet when they got on the field (together), they were there to play football. And to win.”

McCaskey didn’t get a ring from that team’s Super Bowl XX triumph. She opted instead for a pendant that has been securely stored in a safe deposit box. More than that, though, she cherished that group’s championship-level DNA, its relentless mindset and the feelings those players and coaches evoked.

“So much of the normal stress of game days seemed to be disappearing (that season),” she said at the Bears 100 Celebration in the summer of 2019. “You could go to the game and not be completely knotted up inside. There was so much confidence in everyone.”

McCaskey also will forever remain proud of that exhilarating January day 16 years ago when she stood on a platform at Soldier Field amid a majestic scene of snow flurries and presented the trophy that bears her father’s name to the energizing leaders of a Bears team that was headed back to the Super Bowl.

Urlacher and Lovie Smith took possession of the George S. Halas Trophy those 2006 Bears won for capturing the NFC championship, and McCaskey couldn’t have felt prouder.

“I remember wearing my mother’s fur coat,” she said. “That week before the game, people kept asking questions about what are we going to do for this, what are we going to do for that. How many people are going to be on the platform? I just didn’t want to talk about it. Any of it. I was so superstitious. ‘We haven’t played the game yet! We haven’t won the game yet!’

“But those arrangements and those decisions had to be made. Then all of a sudden we were up there on the platform and everybody was smiling and laughing and singing the Bears fight song. That was the way things should be.”

Again, to that, she will find no disagreement.

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Those were also the kinds of moments that often prompted deeper reflection from an adoring daughter about her father, an ambitious leader largely responsible for first lifting the league that has now become a billion-dollar industry and an American treasure.

McCaskey knows how hard her father worked in those early stages, how determined he was to see his vision through and how anxious he sometimes was that his fledgling professional sports league might not catch on.

He channeled that same ambition into how he coached.

“I hope one of the lessons we can all learn from his life is that he realized probably even in his high school years that he didn’t have as much physical ability and, as he used to say, as much mental ability as some of the other people, especially in sports,” McCaskey said. “But that didn’t discourage him. It helped him realize he had to work harder and to do more to accomplish more.”

McCaskey also came to understand over time that George Halas the football coach/player/visionary was so gracefully able to compartmentalize his professional obligations from his home life.

“I realize now he was almost two different people,” she said. “He was a coach, a player, a businessman, the tough guy. Then when he came home he was Dad. And George, the husband. And he was able to keep that division. Yet he remained good at all of it.”

Upon her father’s death in 1983, McCaskey became the Bears majority owner. That was four years after her brother George “Mugs” Halas died of a heart attack. She has been on that perch for nearly 40 years now, hopeful that she and her family can restore the championship legacy her dad established.

Now 100, she has witnessed eight of the Bears’ nine championships and known all 30 of the team’s Hall of Famers. The aspiration of adding to those lists remains strong. And if there was one characteristic McCaskey truly admired in her dad, it was his unrelenting optimism.

“That,” she said, “is the way he lived his life.”

With that in mind, the belief in a more promising future for the Bears remains steadfast.