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In Praise of Virginia McCaskey

| August 25th, 2022


Virginia McCaskey is 99 years old. Let’s put that number in perspective.

– When Virginia was born, sound was still four years away from being introduced to motion pictures.

– Virginia was born two months before the first ever publication of Time Magazine, in March 1923.

– Across the country, other icons were born that year. The Hollywood Sign (reading “Hollywoodland”) was erected in LA. Yankee Stadium and the boardwalk at Coney Island opened in NYC. The Walt Disney Company was founded.

Virginia is not in good health. In the last few days, word has trickled to DBB that her condition has become more serious. At her age, the word “good” is relative. (I just turned 40 and now my neck always hurts. If I live another 59 years, which is highly unlikely, will I even have a neck?) She’s on the precipice of living a century so one could argue that being alive, in any state, is playing with house money. But this seemed the appropriate moment to thank her for what she’s meant to the Chicago Bears franchise.

And where does one start?

Virginia is football’s link between then and now, heir to a founding fortune and keeper of one of this country’s most sacred sporting entities. Even while the family she married into has often caused consternation amongst the fan base, she has maintained her position, often symbolic, with dignity and passion. Virginia understands what the Chicago Bears mean to Chicago, what the Bears mean to their fans around the world, and always encouraged those leading the franchise to do whatever necessary to bring home another Super Bowl trophy. While they have failed, she has not.

It has become commonplace to see female owners in the NFL, in Detroit and Tennessee and Seattle. Virginia has been an NFL owner for 40 years. Not the wife of an owner. The owner. How many other women were running major American businesses in the early 1980s? And how many have not only maintained that role but earned the respect of the alpha male tycoon yahoos that surround her? “She’s remarkable woman,” Jim Irsay told The Score. Remarkable barely does her justice.



My favorite moment as a fan of the Chicago Bears coincides with my favorite Virginia McCaskey moment. In the days leading up the NFC Championship Game in January 2007, the media was giving us every reason the Saints would easily handle the Bears at Soldier Field. The Bears had struggled to get by the Seahawks and were vulnerable. The Saints were an offensive juggernaut. I was getting so angry with this insistence that I called into sports radio shows for the first and only time in my life.

In the third quarter, Reggie Bush took a screen 88 yards for a touchdown and decided to taunt Brian Urlacher. Bears 16, Saints 14. Game on. Then…

Safety called on Drew Brees.

Berrian touchdown.

Benson touchdown.

Jones touchdown.

Bears 39, Saints 14.

At Josie Woods Pub, we opened bottles of champagne to celebrate a long-awaited trip to the Super Bowl and turned the volume up sky high on the postgame ceremony. And there she was. Virginia McCaskey. Holding the trophy bearing her father’s name, George Halas. Yes, we had consumed some alcohol, but the poetry of that moment moistened quite a few eyes in our underground den of debauchery. Virginia would say it was “her happiest day so far.” For many Bears fans, especially those of a certain age, she wasn’t alone in that feeling.

I don’t know how long Virginia has left on this fading planet. (It seems like she’ll be getting out at the right time.) I do know that when she passes, the Chicago media landscape will be inundated with eulogies and tributes, followed by months if not years of familial infighting and rumors of potential sale. (Look for Pat Ryan to make his move.)

Today I just want to thank Virginia McCaskey for honoring the legacy of her father and forging a brilliant legacy of her own. I want to thank her for sharing in our collective passions and disappointments. I want to thank her for representing this organization we love with dignity. There are a lot of owners in this league who serve as a constant reminder that with wealth does not come class. Virginia is all class. All the way.

So, thank you, Virginia McCaskey. And here’s hoping your current health issues are just another blip on the radar and we’re celebrating your centennial in January as the Bears prepare for an unlikely trip to the postseason. I know it would give you the happiest of 100th birthdays.

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