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The night already was a short one.
Just more than eight hours earlier, George McCaskey completed the 70-mile drive from Soldier Field to his rural DeKalb County home. It was 12:30 a.m., and the Bears chairman was well aware of the work assignment that awaited him later that morning.
But as McCaskey jogged from one end of a Sycamore park district soccer field to the other on a sunny August morning, he couldn't help but notice the woman seated in a lawn chair, cheering the play of the nearby goalkeeper.
McCaskey had already walked past her once during a stoppage in play without comment. Instead, McCaskey rolled his eyes, bringing notice of the soccer mom to a visitor standing along the sideline.
“They’re everywhere,” McCaskey sneered with a hint of disgust in his voice. “Packer backers.”
The woman didn't realize that the lone referee working her daughter's recreation league soccer game was part owner of the Bears. She didn't know that it was her baseball cap, trimmed in green, gold and white and emblazoned with the familiar Packers logo, that had drawn McCaskey's ire in the first place.
The grandson of legendary Bears' founder, owner and coach George Halas, McCaskey continued to weave through the young soccer players, following the flow of play. But when a brief break provided him the opportunity, McCaskey made his way over to the soccer mom’s front-row location, unable to keep silent any longer.
“You know,” McCaskey said straight-faced, “we’re trying to promote a positive environment for the kids here.
“And that hat is not helping.”
The woman just laughed, still unaware of who McCaskey was.
But for McCaskey, who has called Sycamore – an out-of-the-way town of 17,500 – home for nearly three decades, the bit of hometown anonymity suits him just fine.
It's here where he can remain inconspicuous even if he belongs to one of the NFL’s first families.
"He does not draw attention to himself, especially as it relates to the Bears," Sycamore Park District President Ted Strack said. "People know who he is, and if they want to talk about the Bears, he'll talk to them. But he's not out there blowing his own horn – at all.
"That is not George."
George and Barb McCaskey's move to the country was an experiment.
Both had worked as writers for Chicago television stations – George at Channel 2 and Barb at Channel 7. Newly married, the couple set down roots in Evanston, which allowed them all the comforts of being close to the city without living smack dab in the middle of it.
Barb had grown up in a small town and so, given the fact she and George didn't yet have children, it made sense that they would give living in a more rural area a shot. Even if it only ended up being for a year or two.
George, who had obtained his law degree from Arizona State, was making good money at Channel 7. But when he was offered a job for $18,000 in 1987 to work in the Lee County State's Attorney's Office in Barb's hometown of Dixon, the couple decided to move. But only after McCaskey managed to bump his salary offer up to $20,000.
Yet, when his boss lost in the next primary election, McCaskey shifted his employment focus to DeKalb County, where he accepted a job in 1989 as an assistant state's attorney in Sycamore. It quickly became home.
George and Barb moved into a home built by Barb's father. Small-town living seemed to suit them. McCaskey appreciated the people who lived in Sycamore. He respected their work ethic, their salt-of-the-earth mentality and their honesty.
In Sycamore, the McCaskeys found a place where people appreciated them for who they were rather than where George – the eighth of Ed and Virginia McCaskey's 11 children – came from.
"Most of the people didn't know about our Bears connection and most of the people who did know, didn't care," McCaskey said in an interview with Chicago Football. "They just care about what kind of person you are and what's in your heart."
Even after he accepted a job offer from his brother, Michael, to become the Bears ticket manager in 1991, McCaskey still knew Sycamore was home.
The town came with a built-in humility and the kind of values system George and Barb found conducive to raising their son, Conor. Barb took on an active role in the community, serving as the music director at Sycamore's Church of St. Mary while also performing in various other community theater and musical venues.
"She's probably more well-known in Sycamore and in DeKalb County than I am," McCaskey said, smirking. "Which is fine with me."
Despite landing a dream job opportunity working for the franchise that meant so much to his family, McCaskey remained commited to his hometown as well. He ingrained himself in the Sycamore youth sports program, first volunteering to work baseball games when the park district experienced a shortage of umpires.
McCaskey had worked as a Pop Warner referee while in high school and umpired baseball games in college. But when his son's youth baseball league faced the reality of having to cancel games if more umpires didn't volunteer, McCaskey jumped back into action.
While his day job – and the strenuous daily commute that comes with it – keeps McCaskey deeply invested in Lake Forest and on game days along Chicago's Lakefront, he remains firmly committed to working with Sycamore's young athletes. McCaskey has a reputation among coaches and players of being stern, but fair. He is a stickler for the rules, making sure that players – even at a young age – respect the way the game is to be played.
No one understands that better than Conor McCaskey.
Conor, who now works for the NFL league office in New York, knew from the beginning that he wasn't going to get any favors from his dad. To avoid any conflict of interest, McCaskey would only work his son's games if no one else could. Even though McCaskey dedicated himself to remaining objective, Conor – even at age 8 or 9 – knew that everyone wouldn't always view it that way.
"I knew all the way through the time I played baseball that if I was at the plate, I'd better be swinging because I wasn't going to get any help," Conor said. "When people made comments about impartiality – and those were few and far between – they clearly didn't know [McCaskey] very well because, if anything, he was going to make it harder on me.
"That was something I had to get used to."
Like his parents, Conor appreciated Sycamore's cozy charm. Despite the miles between there and getting to Chicago for Bears games on Sundays or Blackhawks and Cubs games and matinee theater performances, the separation afforded the McCaskeys what George McCaskey refers to as "blissful anonymity."
It's something that McCaskey still manages to enjoy, even among those who know of his role with the Bears.
"He's just a common guy," said DeKalb resident Chuck Johnson, whose daughter plays in the Sycamore youth soccer league that McCaskey referees on Saturday mornings. "Yes, he's the chairman of the Bears and some people know that. But at the same time, he's just another one of the dads here and I think people here really appreciate that about him."
McCaskey's humble nature also has left a lasting impression on his son.
In a NFL front office world filled with big personalities and sometimes even bigger egos, McCaskey holds down his leadership role with the Bears with the same small-town values he and his family have found in their rural community. He is approachable and friendly, displaying a sense of humor and casual approach to business that his co-workers at Halas Hall have come to appreciate.
After taking over for Michael McCaskey, as the Bears' chairman four years ago, McCaskey appreciates the journey that has led him to this point of his career. It would be easy, Conor McCaskey said, for his father to allow his position to change who he is, allowing the prestige of his post to change who he is at heart.
But that, Conor said, doesn't fit George McCaskey's personality profile.
"He's been put in the spotlight, but I don't think he's ever going to seek it out," Conor said.
Even after rising through the ranks of the Bears' front office, McCaskey has remained dedicated to remaining true – not only to the family tradition that has covered generations, but to himself.
When he took over as chairman after his brother resigned from the post, McCaskey understood how those who had gone before him had approached the job. While in some ways, he was a torch-bearer for one of the NFL's oldest organizations, he understood the need to put his own stamp on the job.
"When you follow George Halas, Ed McCaskey and Mike McCaskey, I realized early on, I couldn't think of that too much," McCaskey said. "I think they would all expect me to be my own person on the job."
How McCaskey has managed to do that, though, follows a long pattern of him being his own man. He leaves player personnel moves to general manager Phil Emery and coach Marc Trestman, focusing instead on establishing a culture around Halas Hall that breeds success franchise-wide.
In McCaskey's mind, that means shying away from the limelight, giving credit where credit is due, and respecting everyone around him – regardless of how big or small their role with the Bears may be. Those who work with McCaskey on a daily basis know him to be easy to relate to and as someone who will never allow his position of power to become a wall between himself and those who work for him.
"He's very much a chairman for everyone," Bears President and CEO Ted Phillips said. "When you have an organization like this, you can talk about family and how close it is, but (McCaskey) actually acts it, too. He talks about it and then he delivers on it."
Since taking over as Bears' chairman, his approach to leadership has been effective, those who work for him say. But McCaskey's style is also genuine, a trait that tends to permeate everything he does – all while continuing the legacy of family leadership set before him by his grandfather, father and brother.
"What he does well is that he respects the past, he has a great passion for the Bears and the legacy and the tradition and the fan base," Phillips said. "But at the same time, he has done a nice job of realizing that in order to be effective, he has to show trust in his people and he has to communicate really well. He has done a nice job of staying consistent in the message he tries to deliver."
McCaskey perhaps draws most from the example set by his father, who served as the team's chairman emeritus until his death in 2003. McCaskey admired how his father created a balance in creating a climate conducive to success while remaining positive in his approach to helping keep the organization on the right track.
That's the kind of road map McCaskey continues to follow. But on the days when he needs reminding of the expectation set before him, all he has to do is walk up the steps in Halas Hall that lead to the offices of most of the people who work for the team in Lake Forest.
On the wall, a quote from the building's namesake and McCaskey's grandfather establishes a theme that defines the job that McCaskey continues to do while pushing for a Super Bowl title that has eluded the Bears since 1986.
For McCaskey, the words ring true every day.
"Nobody who ever gave his best regretted it," McCaskey said, quoting the words that he reads daily on the way to his office. "That's a great way to start the day in my opinion."
Even the days that begin on a park district soccer field surrounded by cornfields.