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Honoring Mrs. McCaskey: Faith, Family and Community

Story by Gabby Hajduk

Ahead of Mother's Day and the Bears Care Gala, the Bears are honoring Virginia Halas McCaskey, who passed away February 6 at age 102. ChicagoBears.com spoke with nearly a dozen people closest to Mrs. McCaskey to showcase who she was as a mother, grandmother, friend and member of the community through personal stories spanning decades.

Just mom. Just grandma. Just Virginia.

To those closest to Virginia Halas McCaskey, she was just that.

Mrs. McCaskey was known to most as the Bears' principal owner, the daughter of George Halas and an NFL trailblazer. Mrs. McCaskey witnessed more pro football history than any individual in the world. But she lived an even fuller life in front of her loved ones.

A life where her legacy reached beyond sport.

She is remembered as joyful and calm. A woman of few words. Present and available. Always smiling. A great example of holiness. Stern and loving. Very competitive. Family-focused and faith-filled. Strong and poised. A will of iron.

Above all, she embodied the word grace, which everyone used with conviction when describing Mrs. McCaskey. That grace was always rooted in her faith.

"She knew that her life was a gift from God," Patrick, her fourth-born child, said.

Mrs. McCaskey's faith — which she displayed by attending Mass daily, giving out Bears-colored rosaries and being at every First Holy Communion, confirmation and wedding possible — influenced every part of her life.

It made her a strong-willed leader but also a gentle, warm matriarch, who in line with her faith, made family her priority.

"That smile," James, her grandson and Patrick's son, said. "Her laugh. It's infectious. That was her aura. There was always a warmth to her. That's what I always loved about her."

Her faith also intertwined with her devotion to the Bears community whether it be members of the Bears family or those around the Chicagoland area who possessed the same love for the navy and orange as she did. The affection she delivered to her own family, she offered to them.

"Every time that I was around her, it really felt like it was just me and her," Jarrett Payton, son of Bears legend Walter Payton, said. "She had this way of connecting with you where everything else around you was silent, and you were just in that moment with her."

Large family gatherings were a key source of that joy. With the lives of 11 children, 21 grandchildren, 40 great-grandchildren and four great-great-grandchildren to balance, Mrs. McCaskey did not experience those moments often, making them priceless.

The best way to round up the family in its entirety was in celebration of her birthday, every Jan. 5. The group would reserve a separate room at a large restaurant — either the Wellington in Arlington Heights, before it closed in 2012, or Giacomo's Ristorante Italiano in Des Plaines — and just enjoy each other's company. Mrs. McCaskey would be situated at the head of the table to watch chaos ensue.

"I feel like some people, especially as you get older, might try to keep people in order, but she just loved it," James said. "She was always very entertained by us. We would be climbing under tables. We'd be doing group renditions of Bear Down, Chicago Bears. I have very vivid memories as a kid in these large family dinners of just having the best time with my cousins and just seeing her laughing and enjoying the moment was the best."

James believed his grandma "loved every second" of those family gatherings, whether it was for various birthdays or family reunions, where dozens would gather in a big room for meals. How could she not? Raising 11 children, she lived that chaos and thrived on it.

Brian, the 10^th born child of Mrs. McCaskey, remembers one of the first times he was amazed by his mother while growing up. Mrs. McCaskey ran a traditional household, while her husband, Ed, rode the train to work each morning. He would return to dinner on the table and chores completed, all 11 children carrying their weight around the house throughout their childhoods.

Mrs. McCaskey often exceeded her children's expectations.

"One of my memories is of her being two stories up on a ladder, painting the gutters," Brian said. "I have to believe she was in her late 40s, early 50s when she was doing that. I wouldn't do that, but she did it. I always thought that was pretty amazing."

Mrs. McCaskey led by example within the family.

Patrick still remembers a lesson she taught him as a little boy. One morning, he was frying eggs and once finished, left the pan on the same burner.

"My mother said, 'didn't your mother ever teach you to take a hot frying pan and put it on a cool burner?'" Patrick recalled. "I said 'no, you told Mike and Tim and Ellen, but you didn't tell me.' Now I take the hot frying pan and put it on the cool burner. That was the lesson."

Mrs. McCaskey offered tough love at times, but her simple messages were clear. It was easy to listen to someone who typically only spoke when necessary.

She held her children accountable in necessary times, like when Patrick carved his initials into freshly laid cement in the basement. But she also offered equal parts encouragement and love. Her softer side typically emerged in the form of showing up. And it looked different for each child.

For Brian, one of his fondest memories of his mother's support came in college, when he was a student trainer for the national champion North Park College men's basketball team. He secured his parents two seats right behind the home bench for each game. Brian vividly recalls a matchup with Augustana, which was a back-and-forth contest until the clock expired.

"We won on a last-second shot from beyond half court," Brian said. "The place went crazy and it was just a really special moment for our team. It was really special for me personally, because my parents were there. It was a thrill to share that moment with them."

For Patrick, showing up came more so in the form of emotional support. In 1983, when he earned a raise, Patrick decided he was ready to get married to his then-girlfriend Gretchen. On Memorial Day weekend, the couple went to tour a house for sale in the neighborhood and Gretchen asked Patrick why he was interested in buying a home, to which he muttered: "in case you want to get married."

Gretchen accepted and within days, Patrick delivered the news to his mother.

"My mother cried and then she gave us her mother's wedding ring for Gretchen," Patrick said. "My grandfather had bought it at a pawn shop for $250."

The thing about Mrs. McCaskey's love is it often came coupled with life learnings. In Patrick's case, his mother's support of his wedding was built through years of her own exemplary behavior.

"Shortly before my mother died, she asked me, 'Have you ever wondered about how better the world would be if there are more couples like you and Gretchen?'" Patrick recalled. "I said, 'mom I learned from you and dad and Gretchen learned from her parents.'

"I wanted to get married when I was in eighth grade because my parents had a great marriage. My mother said it was not perfect, but it was a lot of fun. She was a great example for all of us."

With nearly an 18-year age gap between the oldest and youngest siblings, it was not long before weddings turned into expanded families and Mrs. McCaskey went from mother to grandmother.

But before Mrs. McCaskey could fully embody her new familial role, she was handed a new professional role. In 1983, her beloved father, George Halas, passed away and Mrs. McCaskey became the caretaker of an NFL charter franchise.

"I viewed her as more of a business grandma," Michelle, her granddaughter, said. "I was not quite 11 yet when George Halas passed away and that was the start of her being in charge. We had Mike Ditka as coach at the time, and the team had success. She was out in the forefront as much as she wanted to be, but it was always centered around football."

While Michelle experienced "business grandma" for the first couple decades of her life, she also witnessed the transition to what she refers to as "grace of grandma," which occurred when Ed passed away in 2003.

"Once my grandfather passed away, I think that's where we really saw the grace in her come out," Michelle said. "Because she was flying solo. Even though she had 100 of us technically around her, she was on her own."

While Mrs. McCaskey became a grandma just about annually, each time held the same weight. And she held each "first moment" with her grandchildren near and dear to her heart.

Brian remembers the first time his mom met his son Keegan, who is the second-youngest grandchild. Mr. and Mrs. McCaskey flew back from league meetings in Arizona before driving over to Brian's house.

"That was a very special moment, and it wasn't emotional in the sense of tears, but emotional in the sense of joy," Brian said. "I have a picture of her holding Keegan for the first time. That's a thousand words right there."

Baptisms and confirmations were also priorities. There was a baptismal gown that was passed down through the family that Brian believes was worn by his mom and his uncle George "Mugs" Halas Jr. Sharing moments as a family in the church was of the utmost importance to Mrs. McCaskey.

The baptism for Brian's daughter Kelly held even more significance, given she was born May 13, just weeks after Ed passed away April 8.

"It was a bittersweet moment," Brian said. "The baptism was very special because it was the first time our family had gathered since my dad's passing. It was a small intimate gathering at the Maryville chapel, where my father's funeral Mass had just been. Kelly was, at that point, the youngest grandchild, and it was special for all of us to be together in that time."

The second wave of grandchildren, which included Keegan and James, altered Mrs. McCaskey's ways of showing up.

It meant traveling out Keegan's eighth-grade football game at Loyola, where afterwards they took a picture that now sits on his desk at Halas Hall as one of his most cherished possessions.

It meant being 50% of the fan section, alongside Patrick, during James' pick-up basketball games at Maryville, simply because she wanted to see her grandson play. It also meant understanding the weight of her presence in certain moments.

Mrs. McCaskey would walk into a small grade school gym to watch her grandson's game and instantly be met with every set of eyes in the room. Sometimes people would approach and want to say hello or ask about the Bears or say they saw her at Mass.

But it was never a bother. And it never deterred her.

"Whatever the significance of the event, she was there." James said. "I felt very fortunate about that. I know not everyone gets to have an experience like that or have someone who makes the effort to be a presence. It's something as simple as that, just being there. I think that has such an impact on kids, just showing up. It's cool to be like, 'yeah, that's my grandma.'

"Then as I got older, realizing who she is. As a kid, you're just like, 'oh, it's grandma.' Then you see other people react to her presence. Everyone just kind of stops and you have a moment to realize the gravity of who she is."

For James, one of the most rewarding parts of his life has been teaching his own children about their great-grandmother. With three children under five years old, James takes immense pride in knowing they were all graced by Mrs. McCaskey's presence, even for a short time.

James' first-born, Madeline, is old enough to recognize her great-grandmother. Any time James brings her to Halas Hall and Mrs. McCaskey's photo pops up on a video board, Madeline says, "it's grandma Virginia."

Memories of Madeline and her great-grandmother will always be cherished.

"Seeing the wonder in my kid's eyes of being like, 'this is grandma Virginia,'" James said. "It's something so unique. It doesn't always happen for people. And she's just as warm and cute and welcoming to my kids as she was to me. It didn't matter what they were doing, if it's dancing, singing, she seemed to be always entertained and enjoyed those moments."

No matter Mrs. McCaskey's role, one thing never changed — her love for holidays, specifically birthdays and Christmas.

Mrs. McCaskey never forgot a birthday. Starting with her own children, she always gave a birthday card and a birthday check.

When her children were young, birthdays also meant choosing what meal you wanted her to cook. For Brian, that was usually lasagna and angel food cake with chocolate frosting.

Grandkids received the same card and check treatment. It was always handwritten in her distinctive cursive. There was no better feeling than checking the mail and seeing grandma's card.

"I didn't always see her throughout the year regularly," Keegan, who went to college at Louisiana State University, shared. "And it was always nice to know that the card was coming. I wouldn't get a lot of birthday cards. Most people around my age don't really send them, but it was always nice knowing that hers was coming.

"We are a big family, and it's hard to get everybody in one room just from a life standpoint. So any opportunity that she had to reach out, she would take."

Christmas was always one of those unique opportunities where a larger portion of the family could gather. In the earlier years of Christmas dinners, George Halas and Mugs would of course be in attendance.

The fine China made its annual appearance, real butter would grace the table and the smell of fresh rolls permeated. Once dinner was served, the family would pack in tightly at the large dining room table, which featured chairs at the ends for Ed and Virginia and benches along the sides for everyone else.

While that table remained in use for decades, once grandchildren came into the picture, a "little table" was added. The older adults always sat at the "big table," but the last few spots were up to chance.

"We would always have little slips of paper, and you had to pick out of grandpa's hat," Michelle said. "If you got the big table, that was a big deal. That was a big deal. I got it a couple times."

Throughout every chapter of Mrs. McCaskey's life, her dedication to family remained steady and strong.

Her children and grandchildren could reminisce for hours, their smiles shining just as bright as hers when doing so. There are endless moments to choose from.

Competitive card games of gin rummy and double solitaire, where beating Mrs. McCaskey was a rare occurrence. Entering a time machine when she sporadically told stories of her early life. Enjoying her homemade chocolate ice box cake, a family-favorite dessert.

"Any time with her was quality time," Patrick said.

It is no surprise Mrs. McCaskey raised her own large family with grace. As a child, she grew up surrounded by an immediate family of 100+ players, coaches and staff as well as an extended family of hundreds of thousands. It was the Bears family, of course.

Mrs. McCaskey was born in 1923, just three years after her father helped found what is now the National Football League. Her entire upbringing intertwined with that of professional football and the Chicago Bears. She was raised around the team.

In her adult life, Mrs. McCaskey wrapped her arms around the Bears community like it was her bloodline. That love stretched from players and coaches to staff members to the broader Chicagoland community — a passionate fanbase that poured as much emotional support into her father's club as she did.

Brian Piccolo experienced it first, and his mother-in-law Grace, wife, Joy, and three daughters, Traci, Kristi and Lori were the beneficiaries for years to come.

After joining the Bears as an undrafted rookie in 1965, Piccolo developed a close relationship with Ed, who worked in player relations for the club. Ed leaned on Piccolo to attend events, communicate with the other players and bounce ideas off of.

Through Ed and Piccolo's mutual love, a similar affection between their wives naturally sprouted. And it became crucial when Piccolo was diagnosed with cancer and later passed due to embryonal cell carcinoma on June 16, 1970.

"When my dad got sick, that was really when George Halas basically said to my parents, 'you do whatever you want to, you go anywhere you need to go, get whatever care is necessary and don't worry about it,'" Traci said. "Ed and Virginia stepped in. Ed was with my parents during treatment almost all of the time in New York and Virginia helped here. Her own kids, Patrick, flew back and forth with my sisters and myself to Atlanta to deliver us to my mom's parents. They never batted an eyelash."

Once Piccolo passed, Mrs. McCaskey not only helped keep his legacy alive through the Bears, she embraced his family as her own. Traci and her sisters joined the 11 children, and they were thrown right into the mix while Mrs. McCaskey provided wisdom to Joy and friendship to Grace.

For Traci, Mrs. McCaskey's love felt steady and safe. And it became an integral part of her life.

"You just knew she loved you," Traci said. "There were no bold proclamations or declarations of any kind. Just to be in her presence and just feel her near you, for her to hold your hand or give you a hug or her smile."

Traci's favorite memories with Mrs. McCaskey came in the form of regular lunches with Joy and her mom, Grace. A few times a year, the four women would meet, usually at Olive Garden, and take turns paying for the meal. Mrs. McCaskey and Grace would always have cash, counting their dollars together when the bill came.

"Those were special moments," Traci said. "She wasn't celebrity. Her beauty just radiated from within because of her faith and her love for her family and her love for that team."

While the passing of Piccolo brought Mrs. McCaskey lifelong friendship, it also brought her tremendous grief. She vowed to never grow that close to another Bears player again. Five years later, the Bears drafted future Hall of Famer Walter Payton. Once again, her family grew.

Jarrett Payton believes his father and Mrs. McCaskey connected through their mutual love for life and kind-hearted nature. Walter also spent 13 seasons with the Bears, etching his name into franchise history as a Super Bowl XX champion, a seven-time All-Pro and 1977 NFL Most Valuable Player. His career allowed his friendship with Mrs. McCaskey and her family to deepen year after year.

She also grew close with Walter's mom, Alyne and wife, Connie. In the 1970s and '80s, Mrs. McCaskey and Alyne would sit together in the suite during games. For Connie, who moved to Chicago with Walter from the South, Mrs. McCaskey was a sounding board when she felt lost.

The support Alyne and Connie received for decades became apparent to Jarrett once Walter passed away in 1999 from cancer.

"Around 19 years old is when I really started to see the love she had for my dad and for my family," Jarrett said. "There's pictures from being at Soldier Field and at the memorial service and her talking to me. She always looked you in the eyes. She always had a smile on her face. I always felt like she was a grandma to me and my sister."

For the remainder of her life, Mrs. McCaskey embraced Jarrett and his sister, Brittney. Jarrett remembers sending her an invitation to his wedding, in which the reception would be held at Soldier Field.

He was not sure if she would make it, but of course, Mrs. McCaskey showed up.

"I remember at night everybody wanted to go into the seats to be able to take pictures." Jarrett said. "The lights were off and everybody was saying we can't turn the lights on. And next thing you know, the lights were on. The memory I always think of is that she was in my wedding photos. It's her, my sister, my mom, my wife and myself. That's a memory and a moment that I will never, ever forget."

People like Traci and Jarrett feel immense gratitude to have known Mrs. McCaskey personally and been supported by her love. But there are plenty of others who she provided the same help to indirectly through quiet community efforts, that never had the chance to really know her.

Her entire life, Mrs. McCaskey donated to local charities, particularly those aligned with her strong Catholic faith, and individual people or families in need that she discovered through word of mouth. She also touched thousands of lives through her work with Bears Care, the organization's charitable arm.

Since 2006, Bears Care has issued grants totaling more than $31.5 million to more than 200 qualifying agencies.

Mrs. McCaskey was at the forefront of Bears Care's development and instrumental in assembling the first Bears Care board and served as the secretary.

Barb McCaskey, Bears Care board member and wife of Mrs. McCaskey's eighth child, chairman George H. McCaskey, believes her mother-in-law's determination to continuously do good work allowed Bears Care to soar.

"That reinforced her commitment to Bears Care and all the causes," Barb said. "She saw the work as each individual. I never once heard her use the phrase 'give back.' She saw the Bears and she saw her ownership and her kids' ownership as a stewardship. So it was more of passing it on."

Barb saw "mom," as she called Mrs. McCaskey, thrive at the annual Bears Care Gala and Real Bears Fans Wear Pink luncheon, both of which supported breast cancer research as well as patients, survivors and their families.

Mrs. McCaskey would take the time to speak with each individual who lined up to see her at the events, offering emotional support while continuing to expand financial support from Bears Care behind the scenes.

"Anything that was going on in your life, she would just hold your hands and look in your eye, and you felt like there was nobody else in the world," Barb said. "I've experienced that and the ladies at the Gala and the luncheon, I know they've experienced that. And it's very healing. Even if you're still hurting, it's healing for your soul."

While Barb witnessed that healing energy when she would drive Mrs. McCaskey to and from luncheons, she feels lucky enough to have experienced it firsthand as well.

When George and Barb had their son Conor in December 1990, Mrs. McCaskey did the unthinkable, for the sake of providing that incomparable love.

"She missed two Bears games to be with us," Barb said. "She didn't want to leave us."

Externally, Mrs. McCaskey conducted her generosity as quietly as someone with her type of presence could. Internally at Halas Hall, she went about her business the same way, yet still found a way to incorporate every staff member into her family circle.

When Lee Twarling, now senior vice president of fan/guest experience and stadium operations, started with the club back in 2001, both Ed and Virginia had a strong presence at Halas Hall. Their lead-by-example mentality at work fostered respect and admiration from employees.

When Ed passed away, Twarling felt even closer to Mrs. McCaskey, understanding her life had significantly changed. Her poise and strength in that moment allowed him to see her through a different lens.

"Every time you saw her, you just stopped," Twarling said. "Because that was a moment where you could actually reflect on the fact of where you are. It's always been special to think about her, to have known her, and to know really what she has now set a course for moving forward."

To the Bears family, Mrs. McCaskey always demonstrated grace, humility, loyalty and dedication and in 2015, the club created the Virginia Award to honor employees who represented those characteristics and values.

Longtime and beloved Bears employee Katie Nagle, who passed away last Sept. 2, earned the inaugural award. Twarling remembers every employee thinking: "if they wanted to just keep giving it to Katie, no one will ever disagree with that."

Instead, a year later, Twarling heard his name announced by Mrs. McCaskey as the second annual winner of the Virginia Award.

"Every year, you start to reflect on just how many good people we have here," Twarling said. "I never in my wildest dreams put myself in that category. I just can't think about it that way. So when she said my name, you sit there for a second, and the room is excited and it's very humbling."

The award was established to recognize employees who exceed the highest standards of achievement, but for Twarling, it was not about his work being seen. It was about being seen in the same spirit as Mrs. McCaskey.

"The best part of that whole experience is that you walked in front of the room and you got to embrace Mrs. McCaskey's words and her sentiments and really feel her gratitude for what so many people at the Bears are doing for this organization."

With the Bears Care Gala Saturday evening and Mother's Day Sunday, Mrs. McCaskey's legacy will be honored and her presence in those moments will be greatly missed.

For the McCaskey family, Sunday will particularly feel different. Later in Mrs. McCaskey's life, she urged her children to spend Mother's Day with their own families. Still, everyone made sure to acknowledge her on that day, whether it be by giving her a call, dropping by her house or sending flowers.

Being a mother of 11, a grandmother of 21, a great-grandmother of 40 and a great-great-grandmother of four, it was impossible not to celebrate her.

While Mrs. McCaskey did not desire the attention, she deserved it. Even if it came quietly and gracefully, just like her.