Between two dates on a headstone is a simple dash, but inside that dash is a lifetime. Brad O’Leary filled his completely.
Bradley Sean O’Leary, beloved Dad and Grandad, passed away peacefully on May 6, 2026, in Brady, Texas, surrounded by the family he loved above all else. He was 90 years old. “He made us believe anything was possible. No matter how busy life became, he always made time for us. He laughed loudly, sang in his beautiful, deep voice, told unforgettable stories, and loved expanding our world. He taught us to dream big, believe in magic, have fun, and never stop being a kid at heart. He made us feel we could become anything we wanted. Part of who we are today is because of his example. We love you so much, Grandad. Thank you for everything.” He spent a lifetime in rooms with presidents, senators, Hollywood legends, and world icons, but what he loved most was being with his family. And if you needed to find him at any gathering, chances are he was at the kids’ table, laughing.
He was born on April 24, 1936, in New Hampshire, to John and Alice O’Leary, who passed along not only their name but their work ethic and deep faith. He grew up in St. Louis, where, as a young boy, he sang in a cathedral choir, his rich baritone voice echoing through church walls long before anyone knew how far it would carry him. He attended St. Louis U. High School, earned a Bachelor’s Degree in History and Speech from Saint Louis University, and in 1954 joined the United States Air Force, carrying with him a love of God, a devotion to America, and an unshakable belief in the American dream. What followed was more than a career. It was a life full of adventure and heart. Brad believed politics, done right, was patriotism in action, and he devoted himself to it fully. He became one of Washington’s leading political strategists, raising more than $2 billion for presidents Reagan, George H.W. Bush, and George W. Bush, and senators like Phil Gramm and John Tower. As a pioneer of direct mail fundraising, he appeared on the cover of Campaigns & Elections as “The Billion Dollar Man,” the first to raise $1 billion for political candidates. Friends and colleagues described him as fearless, relentless, and endlessly inventive.
He served as President of the American Association of Political Consultants, a Republican National Committee Regent, and received the Defender of the Constitution Award at CPAC. In Washington, they called him “Mr. Fix It”, the man you called when a problem seemed impossible. Brad thrived on bold ideas and found paths forward where others saw none. Industry leaders often
described him as tough, tenacious, and endlessly inventive — someone willing to take risks others would never attempt. Over the years, stories inspired by his larger-than-life reputation even found their way into books and film. Washington was just one chapter. He moved between politics, media, entertainment, and business, leading Associated Television International, co-owning the legendary Chasen’s in Beverly Hills, co-publishing The O’Leary-Kamber Report, and serving on the board of SMU’s Senator John Tower Center, honoring his dear friend. He authored 27 books, hosted a national radio show on NBC Westwood One, produced award-winning documentaries, including one about his friend Ronald Reagan: An American President. He became a familiar voice on Fox News and appeared alongside commentators like Rush Limbaugh, Sean Hannity, and Glenn Beck. Friends marveled at how, every few years, he reinvented himself as a strategist, broadcaster, producer, entrepreneur, author, fundraiser, restaurateur, world traveler, and succeeded in every world he entered.
His faith always revealed itself through service. In the 1970s, he worked with the U.S. Conference of Catholic Bishops on Vietnamese refugee resettlement, including the Kennedy Center’s Road to Hope, hosted by Bob Hope. In 1981, alongside Robert Evans and Brandon Tartikoff, he helped launch the nationwide anti-drug campaign Get High on Yourself. He served on the board of D.A.R.E., as treasurer of Chuck Norris’s KICKSTART Foundation, helped establish orphanages, and supported programs restoring hearing to children through Breaking the Silence. He also co-produced The Planet Is Alive — a documentary about Pope John Paul II that became the first religious program ever broadcast on Russian television, airing on Christmas Eve 1991. In 1999, he was named Presidential Humanitarian of the Year in Beverly Hills and Hollywood’s Man of the Year. This work rarely made headlines, but those who knew him well witnessed these acts of kindness daily. It reflected the truest measure of the man.
The unlikely stories were always true. Brad played cards with John Wayne, whom he called a friend, dined with Frank Sinatra, became friends with Buzz Aldrin and Elizabeth Taylor, and, through his work with the Catholic Church, played bridge with Mother Teresa and the future Pope John Paul II. God had a way of placing him in rooms where he could make the greatest impact.
Brad had a gift for making any occasion feel like an event. He was the perfect host; he made sure everyone felt like the guest of honor. He loved elegant dining and always knew the best places in every city but was just as happy with a great hot dog, ice cream, good company, and a night of storytelling. At the Polo Lounge at the Beverly Hills Hotel, the staff greeted him by name and led him straight to his regular table. But what truly delighted him wasn’t just the setting; it was the chocolate soufflé he loved.
To his daughters and granddaughters, whom he called “Darling”, not as a formality, but as his warm, natural way of speaking to the women he loved, Brad was both protector and encourager. One of his daughters lovingly called him her “knight in shining armor.” He encouraged every woman in his life to stand confidently and never doubt her strength, intelligence, or potential. Family stories linger in every memory: grandkids piled on top of him as he laughed with that unforgettable smile, while he taught them poker, chess, coin games around the kitchen table, and gin, a game at which he was legendary. He organized laser tag battles and water balloon wars and never missed a chance to raise a glass and deliver a toast that left everyone laughing.
One of his greatest joys was sharing his love of Ireland with his family. His Irish heritage and family history ran deep, and nothing made him happier than bringing those he loved into that world. He took the whole family to Ireland for Christmas, where they stayed in a castle filled with laughter, stories, and memories that will last a lifetime. He didn’t just give gifts. He gave experiences.
The family loves the story of Brad climbing onto a table in a restaurant to sing “Danny Boy” in his rich baritone, leaving the room laughing and crying all at once. He also loved “My Way,” which felt fitting for a man who truly lived life on his own terms. A lifelong sports fan, he passionately cheered for Notre Dame football, the Washington Redskins, and his beloved St. Louis Cardinals, always with spirited opinions and a friendly wager ready.
His Christian faith deepened every year, as did his love of country; the two were inseparable in Brad’s mind. He believed in God, in America, and in the responsibility of every citizen to protect both. He loved long conversations about faith, purpose, and what it meant to truly live, especially with younger family members, whom he encouraged to know what they believed and why it mattered. And he never let anyone forget to vote in order to protect their rights.
Brad spent his final years in Texas with his daughter, Ann, and her husband, George, whose love and devotion meant the world to him and the entire family. Surrounded by family, friends, stories, and lively political conversations, he continued doing what he always did best: making people laugh, telling stories, and reminding everyone around him to live boldly and without fear.
He leaves behind a void as big as the life he lived, and a dash that will never be forgotten.
Brad is survived by his beloved daughters and their families: Ann O’Leary Weems (George) and her children Coy Weems (Tracy), Stacy Weems Collier (Glenn), Rebecca Weems McCoy (Evan), Elizabeth Weems Jones (Jesse), and Katherine Weems Spiller (Luke); Lynne O’Leary Sargent (Stuart) and her children Amy Dunnigan Pruzan (Keith), Laura Dunnigan Raesz (GW), and Stephen Dunnigan (Kirsten); Shannon O’Leary and her son John O’Leary; Erin O’Leary and her sons Donovan and Patrick O’Leary; and McKenzie O’Leary Taylor and her daughters Lyla Taylor and Violet Anderson, Christina Gulla Radke and Tony Gulla (Lauren), and 19 beloved great-grandchildren. He was preceded in death by his parents, John and Alice O’Leary, and his beloved daughter, Susan Gulla O’Leary. The family is deeply grateful to his devoted caretaker, Haylie, for her compassion and friendship over the past year, and to Magnolia Hospice for the comfort and dignity they provided for Brad and those who loved him.
A private Mass and celebration of life will be held for the family. For those unable to attend, the family welcomes memories and condolences through the online guestbook. Friends may view and/or sign Bradley’s online memorial guest book at www.leatherwoodmemorialchapels.com. In lieu of flowers, the family welcomes donations in Brad’s memory to St. Jude Children’s Research Hospital, 501 St. Jude Place, Memphis, TN 38105 or online at www.stjude.org and/or Tunnel to Towers Foundation, 2361 Hylan Blvd, Staten Island, NY 10306 or online at www.t2t.org. and/or St. Patrick’s Catholic Church, 406 South Bridge Street, Brady, Texas 76825. For more information on Brad, please visit BradleyOLeary.com.
“You’ll realize I had one hell of a good time and never stopped laughing.”
— Bradley Sean O’Leary
Never dream too small.