One question has persisted for years among Chicago Bears fans. Will the McCaskeys ever consider selling the franchise? It has been a constant belief that this family is incapable of running a professional football franchise. Since taking over in 1983 following the death of George Halas, they have run a once-regular contender into the ground. They have only two deep playoff runs since the start of the 1990s. The past decade has seen them post just one winning season. Fans are tired of the ineptitude and dysfunction. It feels like only new ownership can save this organization.
While Virginia McCaskey remains the primary owner of the Bears, many have wondered what happens once the 101-year-old dies. While there is a succession plan that would put her son George in control, reports indicate many of the younger generation in the family want to sell the team. Jim O'Donnell of the Daily Herald reported this in 2021.
The most striking reply came from an individual with exceptional knowledge of the working dynamic within the McCaskey family.
That person said: “There is some internal strife going on among family members to sell … now.”
So one can imagine it was fascinating when betting odds dropped, revealing that Amazon billionaire Jeff Bezos is the favorite to purchase the Bears at some point soon.
The Chicago Bears are stuck in the past.
They've tried modernizing for years, but it's apparent the McCaskey family doesn't have the business or football acumen to run the ship like true professionals. This is why they keep running through GMs and head coaches every three to four years. Bezos is rated as the second-richest man in the world. The founder of the tech giant Amazon is worth $229 billion. He has more than enough capital to purchase the Bears, who are valued at around $6.4 billion. It is also not a secret that Bezos has tried entering the NFL arena for years. He attempted to purchase stakes in the Washington Commanders and Denver Broncos.
Both fell through, but Bezos still managed to strike a media deal with the league that sees his Amazon Prime platform showcase Thursday Night Football. His foot is squarely in the door now. The next obvious step would be purchasing a team. The Chicago Bears are a founding franchise in a massive market with a huge fanbase. If making money is his goal, this team makes too much sense. Whether he can pull it off is another story. Minority investors with the Bears, like Pat Ryan, have the right to first refusal on any sale of shares in the organization. That means he would have to sign off on any sale.
A lot needs to happen.
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