In the 100-year history of the Chicago Bears -- along with his grandfather, George "Papa Bear" Halas, his father, Ed, and his brother George -- Michael is one of only four people to ever run one of professional sports most storied franchises. And while Halas won eight NFL titles, including six as the head coach, Michael is the only one to have ever won a Super Bowl.
He's also the only one of the four to have suffered certain levels of failure and even a taste of disgrace.
This one is my story to tell, and I will remember him fondly as one of the most complicated guys I’ve ever covered in my 40-plus years on the beat -- genteel to a degree that wasn't always a plus in the arena he attempted to master but always kind, respectful of me and my family and devoted to his family and the team that has been all of their lives' work.
Full disclosure: He was also someone I was pleased to call a friend after he retired from the game.
He grew up in the family home in Des Plaines, earned his undergraduate degree at Yale, where he lettered as a wide receiver on the football team, and then went on to earn a graduate degree at the Weatherhead School of Management at Case Western Reserve University.
Michael then served in the Peace Corps in Ethiopia before returning to the states to teach business classes — first at UCLA and then Harvard.
He was living in Boston when Halas passed away on Oct. 31, 1983, and he was named the president and chief executive officer of the team 11 days later.
He inherited a team on the precipice of greatness.
Hall of Fame executive Jim Finks had resigned as general manager just two months before Halas’ passing and was replaced by Jerry Vainisi, but Finks’ parting gift was a 1983 draft recognized as one of the best ever. It included Hall of Famers Richard Dent and Jimbo Covert as well as Dave Duerson, Tom Thayer, Mark Bortz, Mike Richardson and Willie Gault.
Legend has it that Finks quit over dissatisfaction that Halas had hired Mike Ditka as head coach in January 1982. But Finks told me a few years later that while he wasn’t happy about Halas hiring Ditka without his input, it wasn’t the only reason he left.
Finks said he knew Halas would be stepping down soon, suspected Michael was the heir apparent and while he didn’t really know him or have anything against him, he knew he’d have to teach him everything and didn’t really want to do that knowing some day Michael would fire him.
In Michael’s first five full seasons running the the Bears from 1984-'88, the team went 10-6, 15-1, 14-2, 11-4 and 12-4 and played in three NFC Championship games, winning one en route to the 1985 Super Bowl title.
Michael was young, just 40 when he took over the team. There was plenty of glory to go around, and he wanted his share. But although Halas was a legend and Ed and George could work a room as well as anyone, Michael’s people skills were awkward at best.
He was never the most humble individual in the world, and with his grandfather and Finks gone, it had become Ditka’s, Buddy Ryan’s and Walter Payton’s team.
If Michael was going to get the glory, he was going to have to take it, and that pretty quickly started to rub some people the wrong way. Following the Super Bowl win, Michael decided to fire Vainisi and -- without claiming the title -- made himself the de facto general manager.
Ditka might as well have been the mayor of Chicago at that point. Vainisi was his best friend, and he wasn’t happy.
Bears fans, of course, sided with Ditka.
The team continued to win — its only losing season a 6-10 campaign in 1989 followed by back-to-back 11-win seasons. But following a complete collapse in 1992 and a 5-11 season, with almost all of the Super Bowl team gone, Michael fired Ditka.
It was the right move, as Ditka had clearly lost his team, but Michael still became public enemy No. 1 for firing "Da Coach."
The Dave Wannstedt era began with promise, including a wild-card win over the Vikings in 1994, but it stuttered on and off after that, in large part due to the lack of a strong front office without a general manager and strong football leadership.
It was during the Wannstedt years that I became closely tied to Michael. He had his own radio show called the Management Report and as the color commentator on the Bears Radio Network at the time, I hosted the show and interviewed him every week of the season.
Because he rarely spoke to the media off the air, I was viewed as having a special pipeline to him, but the truth is he didn’t often share any real intel or insights with me either.
Following a second straight 4-12 season in 1998, Wannstedt was fired and Michael sealed his own fate a couple weeks later in announcing that Dave McGinnis would be his next head coach before McGinnis had a contract or had formally agreed to take the job.
"Mac" decided to pass and move on, leaving a ton of egg on the face of the organization.
On Jan. 24, 1999, Dick Jauron was given the head coaching job, and 10 days later Michael was kicked upstairs when Ted Phillips was named the new president and CEO of the team.
While Michael was named the chairman of the board, replacing his father, Ed, it clearly wasn't a promotion.
However, Michael eventually took to the move well and seemed a great deal more at peace as the team became successful again under Jauron in 2001 and then Lovie Smith in 2005 and 2006.
Though the McCaskey family is obviously quite wealthy, none of the individual members ever amassed anywhere near the riches of most team owners, so Michael always seemed a bit out of place at the league level.
But he did have significant business expertise from his educational background, and he was deeply involved in the push to make the game an international success.
In the years I worked on the broadcast, the Bears played exhibition games in London; Goteborg, Sweden; Berlin and Dublin, making them the most traveled club in the league.
Michael is also credited with starting and growing Bears Care, a model today for charitable endeavors and civic partnerships throughout the NFL.
During the lockout in summer 2011, Michael retired at the age of 67.
He immediately engrossed himself in his passions for photography and travel, and I bumped into him more than once on the sidelines at games while I was working the national broadcasts for Westwood One and he was somewhat anonymously just shooting games as a credentialed photographer.
The last time I saw Michael was a little more than a year ago, Valentine's Day of 2019. My wife and I were waiting for a table at a local restaurant, and he came in with some friends whom he had come back from his home in Boston at the time to visit.
He immediately started grilling me on everything I knew about Ryan Pace, Matt Nagy, Mitch Trubisky and the team. While he seemed as relaxed and at ease as I had ever seen him, his love of the Bears was as great as ever.
Michael McCaskey was neither a soaring success nor a failure as an NFL executive. He experienced the highest highs and some painful lows in his three decades with the Bears. He was often controversial, at times overmatched and his ego was never his best friend.
But in all the years I knew him, he never once acted with bad intent, was always pleasant to be around and was as devoted as one can be to his parents, siblings and two children, John and Kathleen. And he never, ever lost his love for his football team or the city it called home.
And that makes Chicago a poorer place for his passing.