Beyond Bears: Remembering Mike McCaskey’s Real Legacy

With honest determination and vision, the former chairman of the Chicago Bears showed those in family enterprises and beyond how to follow an iconic predecessor and create your own identity. In doing so, he also left behind useful lessons for every leader in how to live, teach, and give back.

Chicago Bears owner Mike McCaskey (L) answers questions at a press conference.

Six months ago, former Chicago Bears chairman Mike McCaskey told me that he eagerly looked forward to returning to New Haven this May for his Yale 55th reunion. “Had a stem cell transplant last month and so far the numbers have been encouraging. I feel pretty good, but I can’t be in public spaces where there are a lot of people. Am hoping to be recovered enough to attend my 55th class reunion in May.”

Sadly, that plan went unrealized. The day of this milestone reunion, McCaskey lost his battle against leukemia and died at a very youthful 76—but his legacy of leadership lives on. Not every management call he made was perfect. However, with honest determination and vision, he showed those in family enterprises and beyond how to follow an iconic predecessor and create your own identity. In doing so, he also left behind useful lessons for every leader in how to live, teach, and give back.

I not only knew McCaskey as a revered personal friend, but as an inspiring HBS teacher, a generous faculty colleague, an encouraging board member of my own institute, and an ambassador to welcome me to my new home at Yale where he’d been an enthusiastic alumnus. To help my new institute at Emory and at Yale, he would welcome me to the Chicago Bears box and introduce me to easily half of the city’s power elite – while still guiding calls on the field. He raced to Yale to help me get oriented to the Eli traditions and help teach my new classes.

Known in the Chicago media world as “Baby Bear,” McCaskey took over the reins from “Papa Bear,” his grandfather George Halas in 1983. Halas had played in both major league baseball and major league football; helped create the National Football League; and coached and owned the Chicago Bears.

When McCaskey stepped off the faculty at the Harvard Business School, none of his HBS colleagues had any idea that this was Mike’s destiny—and Mike may not have either. Halas’s son had been the heir apparent, but he died before he could assume control. Halas’s daughter Virginia then selected Mike, the eldest of her 11 children, to lead the family business. As a former Peace Corps volunteer in Ethiopia and a management professor, Mike had not exactly been groomed for the position—and his siblings let that be known.

Not many of us would comfortably take on this mission, but Mike did so out of family pride, civic duty and Chicago loyalty.

It wasn’t easy. McCaskey had the daunting succession challenge of following a genuine legend. For Mike, his “mission impossible” was to take over “DA BEARS” from Papa Bear. But he did so successfully. “Despite being a lightning rod for fan criticism,” Chicago Tribune sports columnist Brad Biggs wrote, “the Bears had a .539 winning percentage during McCaskey’s 27 seasons, appearing in five NFC championship games and qualifying for the playoffs 12 times.”  They were Super Bowl XX champions in 1985.

Mike served as chairman of the board for another dozen years and helped lead the NFL’s long-range planning and technological advances while locally leading on many philanthropic fronts. Whenever he came to New Haven, he insisted on exploring Ethiopian and Eritrean restaurants drawing on his Peace Corps time which also inspired his outreach to assist Ethiopian communities.

In his retirement, he continued to travel, enjoying his pastime as a photographer and working on a new book, as he shared with me six months ago. “Just about to finish a book, ‘Yale Needs Women’ on the first women undergraduates admitted to Yale College. Even though I dated one of those pioneers, I had no idea how tough the determinedly male culture made life for them.”

One of his most disarming qualities was that McCaskey really listened to you. When he asked, “How are you?” it was not the usual perfunctory greeting. He’d sit back and listen to the reply, with that Rogerian, gentle probing he’d taught in classes, but then would offer candid parallel reflections in his own life, if you asked him.

He was well loved by many from a surprising number of fields as a result. When turned 64, he emailed around a piece by Garrison Keillor, who was turning the same age. The address line caught my eye. It included his friend Ben Bradlee, renowned editor of the Washington Post; Warren Bennis, the Leonard Bernstein of our field; Spencer Johnson, the hugely popular management author/physician; and others who, like Mike himself, have now perished.

In this horrific historic period with so much daily tragedy in the headlines, where we are “Zoomed” to exhaustion, barely leaving our Covid caves, Mike’s passing reminds me of the need to think beyond the crises of the moment. He used to put quotes and expressions on the blackboard in class and I recall him putting “Carpe Diem” on the board one day in 1977 for us to discuss. (Okay, it’s a cliché now, but wasn’t then.) Since he attended Yale, of course he had read ancient Roman poet Horace’s work Odes (23 BC).

At Harvard, this perspective was news to we non-classics majors. I thank Mike for teaching this concept as a life lesson. But he also taught all next generation business leaders how to be great. Mike knew he could never be the next Papa Bear—but he could be the best Mike McCaskey ever. Not a bad goal for any of us to remember.