Timothy Dean O'Leary

July 24, 1928October 6, 2020

The Honorable Timothy Dean O’Leary

Beloved Husband. Proud Father, Grandfather and Great Grandfather. Legend. Hero. Friend. Tim was born on July 24, 1928, in Kansas City, Missouri. He passed away peacefully from death to new life on October 6, 2020, at the age of 92 with his beloved family all by his side.

He grew up in Kansas City, Missouri, attended Rollins Grade School, Westport Junior High School and Westport High School, graduating in 1945 at the age of 16. His family didn’t have any money or a car, so he went to work at 11 years of age selling journal post papers on the corner of 39th and Main. At age 12, he worked for Crown Drug Store delivering products sold to customers on a bicycle at 10 cents an hour. The Drug Store elevated him to soda jerk (malt maker) where he made a little more money. At age 13, he worked for Winstead’s on the Plaza as the first frosty malt maker in the basement. At age 14, he set pins at the bowling alley on 40th and Main. At age 15, he went to Wellington, Kansas, and worked on the Santa Fe Railroad at a car barn, working on freight cars, 12 hours a day, 6 days a week. At age 16, he went to Roswell, New Mexico, and worked for the Santa Fe Railroad climbing telephone poles, 12 hours a day, 6 days a week, all while living in box cars.

Tim went on to serve as a Sergeant in the United States Army Air Corps from January 28, 1946 – December 23, 1948, as World War II was coming to an end. He learned how to build and repair radio teletype units and was assigned to Kimpo Airforce Base, 20 miles from the 38th Parallel dividing North and South Korea. He attended Keo University in Nagoya, Japan for three months, studying advanced electronics. Dad was also deployed to Blanconshire, England at Scanton Airbase during the Berlin airlift to be a gunner. He told his Colonel he had never seen a gun on the B-29, to which the Colonel replied, “Well, do the best you can.”

He graduated from the University of Missouri-Columbia (Mizzou) in 1952 on the GI Bill with a degree in Economics. He was a member of Phi Kappa Psi Fraternity. He would say the best part of college was meeting our Mom, Darlene McBride O’Leary. Dad was a house boy at the Chi Omega house where they met. He would always say it was the best job he ever had. Their first date was at The Shack on campus and the rest, as they say, is history! They went on to marry June 11, 1955, at Visitation Catholic Church, the very place we will honor the end of his life. Tim and Darlene enjoyed an incredible life together – a true love story. They had six children, 12 grandchildren and 1 great grandson. They loved to dance, winning several dance contests. It was common to see them dancing to Frank Sinatra in the living room. Dad always dreamed of the day he would jitterbug again! We smile at the thought of Mom and Dad jitterbugging in Heaven once again!

Tim started as in insurance adjuster for The Hartford while attending night law school. He graduated from UMKC Law School in 1956. He began his law career in the Kansas City Attorney’s Office and then private practice. He was appointed in 1969 as a Judge in the Sixteenth Circuit Court in Jackson County, serving for 20 years before joining the Law Firm of Shughart Thomson and Kilroy, now Polsinelli. He founded the National Inns of Court program for Jackson County Circuit Court, served as President of the Inns of Court, was a member of the Supreme Court Committee on Criminal Instructions, President of the Missouri Trial Judges Association, and Dean of the Trial Bar, among many other positions he held. Besides being known as the best dressed lawyer in Kansas City, Tim received many awards throughout his career, including: the Charles Evans Whittaker Award for Judicial Achievements, Spurgeon Smithson Award for Extraordinary Service and Dedication to the Legal Profession, President’s Award for Contributions to the Cause of Justice, Judicial Achievement Award from the Missouri Association of Trial Lawyers, Missouri University Alumni Achievement Award, Missouri Association of Trial Attorneys Judicial Achievement Award, Ad Hoc Group Against Crime Award for Service to the Community, Special Achievement Award for Justice of the Supreme Court of Missouri, Kansas City Metropolitan Bar Association Dean of the Trial Bar Award, Ross T. Roberts Inns of Court H. Michael Coburn Professional Excellence Award, and ultimately the Lifetime Achievement Award from the Kansas City Metropolitan Bar Association, the highest honor the organization bestows. Upon hearing of his death, his law firm shared, “Tim was an extraordinary lawyer, judge and legal leader. Most of all, he was universally loved and respected as a man of good humor with impeccable integrity. He was a role model for many of us. Tim was a devoted husband to his wife, Darlene, for 58 years, before her death in 2013. Tim loved life, his family, his friends, his colleagues, and his profession. We should all be grateful and proud that he was part of our firm.”

Tim advised his friends at Polsinelli on July 24, 2018, that he was retiring from the active practice of law at the young age of 90. He shared that the past 30 years had been a wonderful experience for him, much attributable to the friendships he had made and working with so many good lawyers. He loved the field of law!

Dad would tell us that God, family and friends are among life’s greatest accomplishments. He loved sharing favorite philosophies and quotes. Some of his favorites include: “Life is not about waiting for the storm to pass, it’s about learning to dance in the rain.” “On the road of life, it is not where you go, but who you are with that makes the difference.” “Suck it up and get going!” “Don’t run with the turkeys, soar with the Eagles.” “Work hard at your job, but work harder on yourself.” “Life is 10% what happens to you and 90% how you react to it.” In other words, attitude is what life is all about! Having a good attitude will help you handle the ups and downs of life.

Tim is preceded in death by his beloved wife, Darlene and son, Ted. He leaves his son Dr. Timothy O'Leary and his wife Kathleen and their children Timothy McBride and Madelyn Grace; son Terry and his wife Lynn and their children Ryan and his wife Maddy and their son Mason Timothy; Brendon and his wife Jackie, Thomas and his fiancé Whitney Walker, Mary and her fiancé Kevin Jacobs, and Amy; son Tom and his wife Jennifer and their children Lindsey, Tommy and Addie; daughter Lorrie and her husband Jon Ritchie and their children John Michael and Megan McBride; and his beloved daughter Megan Mavourneen.

Dad died the way he lived, at peace with God, his family and his friends. He would leave us all with one of his favorite quotes: “Always do right. This will gratify some people and astonish the rest.” – Mark Twain. Dad would then add his own advice: Drink plenty of water. Sleep at least 8 hours. Walk 2 miles a day – with a smile on your face. Don’t envy anyone – you already have more than you need. Make peace with problems of the past. If you don’t care about other people and just live within yourself, you will lose the best of life. However good or bad the situation, it will change. Smile and laugh more – much more. Keep a balanced life – work hard, be a person of integrity, keep your word, develop and maintain a good sense of humor, be a person of good will, truth, honor and integrity, and God will smile on you. Find the best in others. Give of yourself. Leave the world a little better. Don’t go to bed mad. If you make a mistake or something bad happens, stop it, get over it and move on. Do not hold grudges. If you don’t forgive others, the person you hurt the most is you. Walk humbly with God. Call your parents often. Be nice to old people, especially your Grandfather Tim! And above all, The Best Is Yet To Come!

Come celebrate Tim’s life with us at a Drive By Visitation on Friday, October 16th, from 2:00pm to 4:00pm, behind the Temple Mausoleum in Mt. Moriah Cemetery, 10507 Holmes Road, Kansas City, MO 64131. Please use the south cemetery driveway to enter for the visitation. There will be a private family Mass of Christian Burial on Saturday, October 17th at Visitation Catholic Church, followed by a private family burial at Mt. Moriah Cemetery. Friends are invited to view a livestream of the funeral service on Saturday the 17th at 9:00am at or scroll down on this page to the "Services" and click on "Join Livestream:.

Donations may be made to Catholic Charities of Kansas City-St. Joseph.


  • Drive-by Visitation

    Friday, October 16, 2020

  • Private Mass of Christian Burial - Livestreamed

    Saturday, October 17, 2020



Timothy Dean O'Leary

have a memory or condolence to add?

Michael Surface

October 20, 2020

The O’Leary Family. Terry, you have our most sincerest sympathies. I enjoyed your father immensely through the years. A great sense of humor and I loved the stories. A most engaging person, that always tipped his hat or stopped to say hello. He will be missed. The Surface Family.

Bill Prugh

October 17, 2020

Both Leaf and I will miss Tim and mourn his passing. Tim and I were law partners for many years. I was also with him at the rehab place where we recovered from illness. I know I will be with him again, I hope. Best wishes to his family and many friends.

Glenn Bradford

October 14, 2020

I could not let Judge Tim O’Leary’s death pass without making note of my affection and high regard for Tim as a trial judge, outstanding mediator, wonderful, fun person, and occasional tennis buddy. Tim has died at the ripe old age of 92. Tim had a personality the size of a school bus. He performed his various legal duties as a lawyer, judge, and 30 year mediation pioneer effectively and with grace and in a good spirit. Tim was a role model for many a Kansas City lawyer, including me. RIP my friend.

Patricia Steele Longan

October 14, 2020

May knowing how loved your father/grandfather was, be a great comfort to all the O’Learys. My parents, Jim and Gloria Steele, always treasured their friendship with Darlene and Tim. This was evident when mother and Tim found themselves residents at Mission Chateau. Having lunch or dinner with Tim, enjoying his stories, wisdom and quick wit was a joy for mother and me. He made mother’s short 6 months at Mission Chateau a joy. His memory will be cherished by many. Sending love and prayers to all the family.

Michael Saunders

October 13, 2020

Sorry to hear of Tim's passing. He was always had a great story to pass along when he visited our store, Mark Shale, and I certainly enjoyed our visits. I know almost all of you kids and I know your hearts are breaking right now. Thoughts and prayers to you from your long time old friend, Satch

Benjamin Lewis

October 13, 2020

Judge O'Leary hired me as his law clerk and bailiff in 1980. He was the great mentor of my legal career. He taught me that while we deal with life's worst problems, there is no reason not to have a sense of humor.He taught me that even if the lawyers failed to bring us the correct legal answer to a problem our [actually my] job was to keep at the books and find the right answer. He taught me how to deal with complex cases and towering egos when he was assigned to the Hyatt Sky Bridge cases. He taught me that he could run up four flights of stairs faster than Judge Hanna. And he taught me that family is more important than anything we do at work. Living in Cape Girardeau, I did not see Tim often but he always had a kind word when our paths crossed. I will always miss him.

Benjamin Lewis,
Presiding Judge, 32nd Circuit

Mary Ann Popper

October 13, 2020

Mary Ann, Julianne and Robert Popper send deepest sympathy to the O'Leary Family.
And know that Bob would join us in remembering Tim as a fine, loving man blessed with wit, intelligence and warmth.
We all loved you, Judge!

Valorie Peters

October 11, 2020

What a privilege to be given the opportunity to call this consummate gentleman a friend. As a Mission Chateau team member, I will remember many examples of Judge's daily shared wisdom. What sticks with me most? The sparkle in his eyes and the sound of his ornery laugh.

Thomas Kokjer

October 11, 2020

The Kokjer family sends our thoughts and prayers. Your dad was one my dad's favorite friends and my mom was a big fan! Later in life he and I would talk occasionally by phone. What a guy.

Barbara Bloch

October 11, 2020

Terry, It sounds like your dad lived an amazing life and I love how he lived his life. A lesson for all of us to learn. I know it will leave a huge void in your family but think of all the beautiful memories you have to cherish. My prayers are with you and your family during this most difficult time


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