McCaskey, 96, said her life was ordinary for the first 60 years - she was just a mom raising her 11 children. But that all changed in 1983 when she became the owner of the Chicago Bears.
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She discussed her love for the game, her favorite Bears memory and what this weekend's celebration means to her.
Miller: What does it mean to be celebrating 100 years of Bears football?
McCaskey: "I always hope that our present-day players and coaches once in a while give a little thought to the early teams and the beginnings of the National Football League."
What made you fall in love with football at a young age?
"It was so important to my dad (George Halas), and that was his life. And anything that was important to him just automatically became very important to me."
What would your dad think of a weekend like this?
"He would enjoy it. One of his favorite nights of the year was always the alumni party. You know, this is the alumni party on steroids!"
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Do you have a favorite moment that you always cherish?
"When the Bears won the championship game in '06, I was on the field receiving the George Halas trophy, wearing my mother's fur coat. I think a re-run of that would be very special."
Do you hate losing?
"My children would probably have a few words about that! (laughs) My family knows and they understand it's not a pretty scene."
How much pride do you take in being one of the first women of football? Of being the matriarch not just for the Bears but for the league itself?
"Pride is a word I try to avoid because I'm in this position due to my inheritance. I haven't done anything to earn it. I still consider it a man's world and I'm very grateful to be involved as much as I am. I think it's a great privilege and I have to make sure that I don't disappoint."