For a long time, I have tried to understand who the McCaskey family are, as people, not as the villains many fans wish them to be. Here is a collection of direct quotations from individuals have known, worked with, and interacted with the family over the last decade or so.
"They are genuinely good and kind people. The really, really care about the Bears, and the city of Chicago."
"There is this belief that the family is a monolith with one opinion but there are so many kids and grandkids that they rarely agree on ANYTHING. And only a few of the younger generation seem to care enough to have opinions."
"They're a kind of Catholic you rarely see anymore. They're driven by it, and they are exceedingly loyal (to a fault) because of it."
"At the league meetings, Ted did all the hobnobbing and dealing for years. But George always had an aura about him. When he spoke, everyone listened. And he was something of a counter to the money grabs of Jerry and Bob." [Those are references to Jones and Kraft.]
"They are the least business savvy owners in the league. And I can't imagine there is a close second. The other legacy owners - Hunt, Rooney, Mara - they know the business of the league as good as anyone. The rest of the owners made their money in business. The McCaskeys are these weird outliers."
"I have seen you [referring to me] write about hands off they are as owners, and that is true. But as soon as things start to go wrong, that changes. They get involved. But it's clumsy because they don't have any real solutions."
"I was in a room with a few generations of the family once, discussing serious shit when it comes to the Bears. Half the room was on their phones. I remember looking around and thinking, this team needs a real owner."
There will be more columns like this as I continue speaking with folks. But I think this brief survey of quotes begins to tell a distinctly unsurprising story.
