Virginia McCaskey shuffled into the building named after her late father and then the auditorium named after her deceased brother.
It was the Monday before the first game of the 2018 season, and the Bears’ matriarch — she’s technically the secretary of the board of directors, a title that belies her impact on both the franchise and the NFL — had been asked by coach Matt Nagy to address the team.
She was nervous.
McCaskey couldn’t remember the last time she spoke to the entire roster. Former coach Lovie Smith used to have her address the team’s rookie class. She’d give a short speech and then take questions from the players, educating them about the history of the team and the responsibility they held as its newest members.
She spoke a few times when her father, Bears founder George S. Halas, put out an autobiography. But that was a decade before most of the current Bears were born.
It was nothing like this.
Wearing a navy Bears polo shirt, she sat at a table at the front of the room. For a half-hour, she told the story of the franchise that was inextricable from that of her own life.
“I didn’t want to blow the opportunity,” the intensively private McCaskey told the Sun-Times last week in a rare sitdown interview commemorating the team’s upcoming 100th season. “I didn’t want them to think of me as some little old lady that’s just hanging around. And, ‘What’s she really doing here?’
“I wanted to let them know how much I cared about the team, and all of them.”
A little old lady?
“Well,” she said, smiling, “I am.”
She’s much more, though.
Her son George, the Bears’ chairman since 2011, runs day-to-day operations alongside president/CEO Ted Phillips. But at 96, McCaskey is the NFL’s oldest owner, its grande dame — though she would bristle at such a lofty term — and the most direct link to its very founding.
As a toddler, she rode the train on a barnstorming tour that kept the NFL alive. At 9, she attended the NFL’s first playoff game, held indoors at a three-year-old Chicago Stadium that still reeked of circus animal dung.
She and her late husband, Ed, raised eight sons and three daughters in a modest home in Des Plaines, content to dodge the spotlight. But her only sibling, Bears president George Halas Jr. — nicknamed “Mugs” by his father — died in 1979. When “Papa Bear” died in 1983, he left his daughter, then 60, control of the team.
It’s a responsibility that has never lifted from her shoulders, even 36 years later.
It never will.
“That’s my main focus,” she said. “Hoping to do well to justify my dad’s faith in me.”
She spent her third birthday on the Red Grange Tour. Days after the Bears signed the Illinois running back, the most famous college player of his era, they embarked on a 19-game, 67-day barnstorming tour in November 1925.
The Bears would travel more than 7,000 miles by train, stopping to spread the gospel of a professional league that was miles behind the college game in popularity. It was a grueling trip for the players, Halas and his wife, Min. She had given birth to “Mugs” in September 1925. Virginia turned 3 that January.
After the Southern leg of the tour, Min decided to take her young daughter and nursing baby back to Chicago.
“A trip to the West Coast just seemed to be a little daunting, even for her,” McCaskey said.
McCaskey’s memories of the trip are limited to stories told to her later by her mother and aunt. But she appreciates her place aboard the train, and in NFL history.
The roots of America’s most popular pro sport sprouted when Halas and other upstart owners sat on the running boards of a Hupmobile in a Canton, Ohio, car dealership in 1920. But it didn’t truly begin to grow until the train tour.
Without it, the league might have died on the vine.
“It’s a special feeling to be part of that Bears history, which was very significant in the survival and history of the team,” she said. “And for George Halas.”
McCaskey was attending Drexel Institute in Philadelphia when she met Ed McCaskey. The two began dating and together attended the Bears’ 1942 NFL title game against the Redskins in Washington. Ed planned to ask Halas for his daughter’s hand in marriage — until the Bears lost 14-6.
“Early on in my childhood, I realized that if I really wanted something, the best time to ask was after the Bears won a game,” she said. “When we didn’t win? ‘Let’s wait awhile.’ ”
They eloped on Halas’ birthday.
“Well,” she said, “it all worked out.”
She and Ed were married for 60 years and two months when the Bears’ chairman emeritus died in 2003. The McCaskey family kept growing — today, she has 21 grandchildren, 29 great-grandchildren and two great, great-grandchildren.
She has seen all 28 of the Bears’ Pro Football Hall of Famers in person — and has been alive for all but 36 of the Bears’ 1,386 games.
She witnessed the most dominant defense in NFL history stomp its way to the Super Bowl after the 1985 season. McCaskey invoked Mike Singletary, Richard Dent and the rest of that squad when she talked to last season’s Bears, saying the best teams have always carried themselves with an air of confidence.
In January 2007, she accepted the NFC Championship trophy, named for her father, when the Bears routed the Saints in the conference title game.
Ask for her favorite moment in the Bears’ first 99 seasons, though, and she returns to her father, a man she idolized on and off the field. She admits that it might not be the team’s greatest game, but, rather, one she finds the most important.
“Papa Bear” had returned to coach the Bears in 1958 after a two-year hiatus. He went 38-25 over the next five years. Fans had begun to wonder whether, at age 68, the game had passed him by.
Then the Bears went 11-1-2 during the 1963 regular season and hosted the Giants in the NFL Championship Game at Wrigley Field. In temperatures near 0, the Bears won 14-10.
“People had been critical of my dad at that time, and he was 68 years old — which, now to me, seems young,” she said. “People were calling for his retirement, and he just showed ’em all that he still could do it. And he did it.”
The franchise is touting its Bears 100 Celebration, a three-day gathering that begins June 7 at the Donald E. Stephens Convention Center in Rosemont, as the largest collection of former and current Bears ever assembled.
McCaskey will be at the reunion. She’s eager to catch up with the Bears’ former players, though she demurs when asked which one she’s most looking forward to seeing.
Truth is, her two favorites have long since passed.
“Walter,” she said quietly. “And Brian.”
Ed and Virginia befriended running back Brian Piccolo when he joined the Bears. They comforted Piccolo when he was diagnosed with cancer — and comforted his widow, Joy, when he died at age 26 in 1970.
The Bears honor him every year by raising money for cancer research and giving two players — a veteran and a rookie — an award in his honor. It cites a player’s courage, loyalty, teamwork, dedication and — fittingly — sense of humor.
“His memory is very much alive,” she said. “I hope that each year the players will learn about him and gain from that knowledge. And realize that it’s a special thing to be a Chicago Bears player. It’s a responsibility, and it’s a privilege.”
When Piccolo died, she vowed not to grow close to another player. The pain from losing him was too great. That changed five years later, when the Bears drafted Walter Payton. Short of Halas himself, none of the Bears’ Hall of Famers exemplifies the team ethos more than their all-time leading rusher.
“He cared about people — as did Brian,” McCaskey said. “He always made it seem like you were doing him a favor by speaking with him or recognizing him. He was a very different person.”
The Bears’ greats view her in the same way.
During Pro Football Hall of Fame weekend, McCaskey and George, her eighth child, went from the team’s exhibition game to linebacker Brian Urlacher’s party in Canton, Ohio. She arrived at 12:15 a.m. Urlacher froze and ran straight to her. She stayed and mingled for an hour.
Not typically prone to gushing, Urlacher couldn’t believe it the next day.
“She walked into the room,” he said then. “And everyone was like, ‘Whoa — that’s George Halas’ daughter.’ ”
As a girl, McCaskey wasn’t showered with attention simply because of her last name. Short of the occasional perk — she once brought a Grange autographed photo to school to prove the doubting boys in her class that she knew the great running back — McCaskey was raised in a family struggling to get its business up and running.
“When I was growing up, being associated with the Bears didn’t mean anything,” she said. “And I told this to Matt Nagy’s four sons — when my dad was head coach of the Chicago Bears, nobody cared. Now his stories are in the papers almost every day, even in the offseason.
“When our children were growing up, it was with the expectation my brother would be in charge. For most of my life, I enjoyed just going to the games and not having any of the responsibilities.”
When she inherited the Bears, she took on the challenge out of obligation.
“It was very important that the right people be in place and that we stay true to the Halas tradition and the Bears tradition,” she said. “I hope we can continue to do that.”
She spent more than half her life content to stay in the background. But she’s pleased to continue a family business that her son Pat has said — and the family often repeats — will stay intact long after her passing and “until the second coming.”
“It’s something that to me has been a gift,” she said. “We’ve worked hard — and certainly my mother and dad in the beginning had some very difficult times, if you know your history. That’s the way I grew up. That’s the way our children were brought up.”
At the NFL’s annual owners meeting in March, NFL Films screened a documentary, “A Lifetime of Sundays,” that featured four iconic women of the sport: McCaskey, the Lions’ Martha Firestone Ford, the Steelers’ Patricia Rooney and the Chiefs’ Norma Hunt. The film was co-produced by Jane Skinner Goodell, the wife of commissioner Roger Goodell, who convinced the notoriously private McCaskey to participate.
The first lady of the league, McCaskey was the only one of the four women born into her role. The other three married into football families.
Asked whether she gives advice to other powerful women in professional sports, McCaskey tried to downplay her place in league history.
“I try to avoid that because I feel that I’m in this position because I inherited it,” she said. “I didn’t do anything to earn it. I didn’t work for it in any way. It was something that happened to me.”
She’s thankful it did.
“I feel mostly a feeling of gratitude, especially in recent years,” she said. “The fans have stayed with us. And it now looks like we’re going to be enjoying a challenging schedule. And some real old-fashioned — and new-fashioned — Bears football we can all enjoy.”
An hour before kickoff of their rivalry game in December, McCaskey and son Pat made their weekly visit to say hello to opposing brass in their luxury box. With a win against the Packers, the Bears would be guaranteed their first playoff berth in eight years — a period that spanned three general managers and four coaches.
“The Packers people were very gracious,” she said. “They said if they’re not in it, they’ll be rooting for us.
“I’m standing there thinking, ‘They’re nicer than I am.’ ”
Old rivalries don’t die. Neither do the emotions.
McCaskey might not cry after losses as often as she used to, but they still hurt.
“I care very deeply,” she said.
And the wins feel fabulous, though she’s superstitious about talking about them. The Bears have won only one playoff game since they took home the George Halas Trophy after the 2006 season — and six since their last Super Bowl victory. After a 12-4 season, momentum is at its highest in years.
McCaskey’s schedule has slowed in recent years. She stopped driving two years ago but is happy to have a driver who doesn’t mind her pre-dawn wake-up calls and early-morning mass trips. She doesn’t go out much after dark. But she goes to see every Bears game in person — at home, on the road, at noon or at night.
Her favorite stadium?
“Wherever we win,” she said.
And when they don’t, she shares the same disappointment as fans would. Just maybe not the same language.
On the day the Bears fired general manager Phil Emery and coach Marc Trestman 4½ years ago, George McCaskey said his mother was “pissed off” with the Bears’ performance.
“I didn’t use that expression,” she said.
Her son paraphrased, she said. But the story stuck. It even reached the convent. McCaskey’s friend, a nun, talked to her after hearing the phrase.
“She said, ‘Don’t be too mad at George,’ ” McCaskey said with a smile.
In her 96 years, McCaskey has seen the NFL evolve from a fledgling league to the king of American sports.
“I’d like to think it’s the game itself — that it’s the attraction,” she said. “And whoever the owners are, whoever the coaches are, whoever the players are, they’re all a small part of the big picture.”
What would her father think of the big picture? She thinks he’d blush at the salaries players receive — including that of outside linebacker Khalil Mack, whom the Bears gave a six-year, $141 million deal in September, the richest contract ever handed a defender.
He’d be amazed by the renovated Halas Hall, which, at the cost of about two-thirds of Mack’s contract, will double in square footage by the time the season begins.
“I think he’d probably say, ‘They have no more excuses for not being the best,’ ” McCaskey said of the construction. “Because this is the best.”
Her office will stay the same as it was before construction, but for a new coat of paint.
It was Ed’s. She didn’t want to leave it.
When the Bears begin their 100th season, McCaskey will have the same goal she has had since she inherited the team: Make her father proud.
“He could have done things differently,” she said. “Some owners have planned to sell the team instead of handing it on to the next generation. He had faith in me after ‘Mugs’ died.
“I hope to justify the thing.”