Leo High School’s Bill Holland was always most comfortable in a crowd, whether it was in football stands, a gym, a tavern or his own kitchen entertaining friends with his wife, Cathy.
“Bill was born on New Year’s Eve,” said Cathy, “so he’d always say, ‘Everybody parties on my birthday!’”
A Holland-like crowd will be in attendance on Friday night, Jan. 20, in Leo’s storied gym for Bill Holland Alumni Night to highlight a basketball game against its oldest rival, Mt. Carmel.
“My two brothers went to Carmel, but they’re sitting with us on Friday,” said Cathy.
The game is being played in memory of Holland, Class of 1973, a Leo Advisory Board member and loyal Alumni Association activist. A share of the gate and sale of Blackout Night T-shirts—available at the door—will go to the Bill Holland Scholarship Fund.
Holland’s wife chose a crowd last month to bring in the new year and salute her husband of 45 years who died unexpectedly on June 11, 2022. During the impromptu late-afternoon gathering at Cork & Kerry Tavern in Beverly, a split-the-pot effort surfaced amid the merriment. The collection for the Bill Holland Scholarship Fund generated $1,900 to close out a truly happy hour in a heartbreaking year.
“The winner didn’t want to split the pot,” Cathy said, “and gave us all the money for the scholarship fund.”
And so it goes for Bill Holland, even at his wake. In recent months, Cathy and daughters Colleen, Mary Kate and Patty have been anxious about the challenge of sustaining a scholarship year after year.
Jim McEldowney’s response to that worry was succinct.
“Where’s the line, and how much do you need?”
That response, which speaks to those from the 1973 Leo class who pledge to continue tuition payments for a Leo student every year going forward to honor their classmate.
“This guy,” McEldowney said, “would give you the shirt off his back, and, in my case, literally did.”
According to McEldowney, Holland’s appetite for life “moved him up a couple of weight divisions,” so all the XL black-and-orange Leo shirts went to “Jimmy Mack,” a friend of Holland and 1973 classmate who captained Leo’s finest modern-day basketball team.
McEldowney will be in attendance at the event to rally a young Lions squad and remind his peers to support the Holland Fund.
“There are many people out there who Bill has helped,” McEldowney said, “so please give what you think is right—and then give a little more.”
Just like Bill Holland did.
Tipoff is set for 7 p.m. Alumni are invited to meet at the Evergreen Park American Legion Post, 9701 S. Kedzie Ave., where buses will depart for Leo at 5:30 p.m. The buses will return to the Legion post after the game for a pizza and open-bar reception.
Holland attended every Leo Alumni Golf Outing, until last summer.
Universally missed by 400 alumni golfers at the event, the Beverly resident still held sway over the gathering. While in previous years the Leo alumnus would be embracing his fellow alums of all eras, others honored his memory with action.
Holland’s family—led by Cathy—gathered around Leo President Dan McGrath, who stepped to the podium, hushed the crowd and announced that the outpouring of sentiment and monies collected since the event “would cover the tuition costs for a young Leo man” to graduate from Leo in 2025, a year short of Leo’s 100th anniversary as a school dedicated to steering young men off the streets of Chicago and onto the highways of success—and back again to 79th Street, where Holland ran as a kid crisscrossing from Little Flower School and parish, O’Hallaren and Dawes parks, McDonald’s, Wood Street and the backyards of all his lifelong friends.
“I am reminded of Bill each day,” said boyhood friend Tim Miller, “through a phrase, a joke, a song that keeps us close despite his passing.”
The Bill Holland Scholarship Fund was as inevitable as a Bill Holland laugh because of his love of and commitment to his school, whether as a football player or the driving force behind another alumni success.
Holland lore graced every table at Gleneagles Country Club on July 27, the final day the historic course would host a major outing before closing its doors.
Leo was but one slice of Bill “Dutch” Holland’s life.
From the time his daughters can remember, the big, burly Irishman would walk through the Holland front door and howl: “Are there any little girls here who love me?”
His daughters would melt into their dad’s arms followed by three hugs and questions about their day.
“Every day he did this,” said Colleen, eulogizing her father at St. Barnabas Church. “Dad showed his love through his actions. He lived the Leo motto, ‘Deeds not words,’ though he was never short on those.”
While Holland cherished his role of father, when daughter Colleen and her husband, Sean McWalter, had children of their own—Conor and Maura—“Dad” became “Big Papa” in a role he was born to play.
The first few notes of “The Star Spangled Banner” would always wobble Holland, followed by the welling up of tears, and his wife would lean over and ask, “Are you crying again?”
To his daughters, his emotions “showed us how to value the important things in life and never take anything for granted.”
A family tradition on Christmas Eve for the Hollands included watching “It’s a Wonderful Life” because Bill grabbed the real-life mantle as “the richest man in the world” because of his family and friends.
“Many called Bill their ‘best friend’ because he was the best,” said his brother, John Holland. “If you needed him, he was there. If you needed someone to talk to and give you a real thought-out answer, he would.”
A great communicator—if not a boundless storyteller—Holland took to social media to connect with those he cherished. That skill and keeping up with technology served him well as an insurance broker for more than 30 years at Arthur J. Gallagher, where his colleagues and clients were, first and foremost, friends.
Using the latest emoji—matched to acronyms—Holland didn’t turn his posts on social media into cliches; rather, he created puzzles to embed the meaning of his message.
His go-to messages included HITYTHMILY and HITYTHPIAOY: “Have I told you today how much I love you?” and “Have I told you today how proud I am of you?”
Holland found his best friend and true love in the Bogan High School driver’s-education parking lot in the early 1970s. Partnered in driver’s-ed class with Cathy Duhig, of Queen of Peace High School, Holland met his match and future wife.
For them, there’d be an open road ahead full of merriment, and Cathy scored the first giggle.
Seated on the passenger side of the auto, Cathy toyed with the cherub-faced Leo man behind the wheel. As he gave the car gas, Cathy pressed the instructor brake pedal on her side, confounding her new friend. With a quick release, the car bolted forward much too fast for student drivers.
However, a shocked Holland had no idea that he’d driven straight into a wonderful bit of foreshadowing.
“Mom made Dad laugh every day just being herself,” said Colleen.
Holland’s pet names for his wife of 45 years included Orkin (when she bugged him), Little Shark (when she was hungry) and Duhig (when he couldn’t get her attention), just to name a few.
“But the sweetest nickname they both had for each other was ‘Little,’” said Colleen, “though their love for each other was anything but.”
Mary Kate echoed the sentiments of many others.
“Not only did he have the biggest, brightest smile; he also gave the best hugs—a true bear hug—and the warmth and truly genuine embrace always made you feel safe and loved.”
Patty spoke of the impact her father had on her life.
“He was the most significant guy in my life,” said Patty. “Dad was one of my best friends and sounding board. Hearing his loud tone of voice and whole-hearted laugh could bring a smile to anyone’s face.”
Only one wall ever stood between her parents, albeit an unnecessary one in the undersized kitchen, where the couple would create memories singing, dancing and laughing before their kids arose for breakfast.
“It took 37 years to knock that wall down and even longer for Dad to admit it was a good decision,” said Colleen. “Once Dad saw how happy he made Mom with the build-out, he knew it was the right decision, and that made him happy. That was his ultimate goal in life.”
Cathy said her husband was her “catalogue husband.”
“I swear I ordered him from a catalogue,” she said. “He was that great. He broke the mold.”
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