Thomas Sexton O'Brien

Thomas Sexton O'Brien, 77, of Chicago, Illinois, passed away after one hell of a fight, on May 6, 2025. A beloved husband, father, grandfather, brother, and friend, Tom lived a life characterized by kindness, generosity, and unwavering dedication to his family and community. Born in Woodstock, Illinois on August 24, 1947, Tom graduated from Marian Central Catholic High School in 1965 before earning his Bachelor degree from Saint Joseph College in Rensselaer, Indiana in 1969, and later completing his MBA at DePaul University in Chicago. He was a proud U.S. Navy Veteran who learned to fly jets to serve his country in 1969 and then later served proudly in the Naval Reserves.
Tom built a successful career in insurance while maintaining a steadfast commitment to service and community involvement. He served on numerous boards, including the Arditti Board of Risk Management at DePaul University, the Board of Trustees at St. Joseph College, and the St. Vincent DePaul Society and was a proud member of both the University Club of Chicago for more than 50 years and of Team Cuisine, with whom he pedaled RAGBRAI. A man of great faith, Tom was an active parishioner at Saint Francis Xavier in LaGrange, Old St. Patrick's, and most recently the Shrine at Our Lady of Pompeii, where he regularly served as a reader. His commitment to civic duty was evident in his service as an election judge in Cook County in recent years. Tom was an avid athlete throughout his life. In his youth, he played high school, college, and semi-professional football. Later in life, he completed the Chicago Marathon in both 2002 and 2005, demonstrating his determination by training for his first marathon at age 55. For 30 years, he participated in RAGBRAI (Register's Annual Great Bicycle Ride Across Iowa), cherishing the friendships formed during those summer rides across Iowa. Tom had a special love for Door County, particularly Washington Island, where he created lasting memories with dear friends. He proudly marched in Chicago's St. Patrick's Day Parade with the St. Joe's Group and remained a loyal Chicago sports fan, refusing to choose between baseball teams and maintaining unwavering hope for the Bears despite perpetual heartbreak. One of Tom's greatest strengths was revealed when he was widowed at 45, losing his beloved first wife, Diane, to breast cancer. He faced this profound loss with courage and grace, continuing to be an exceptional father to his three children during their time of grief. Tom is survived by his loving wife of 26 years, Susan Kelly Madden; his daughter Kathleen O'Brien Kathman (Brian) and their daughter Stella; daughter Bridget O'Brien Finn and her children Emmet, Aidan, and Drennan; son Thomas Eugene O'Brien (Colleen McMahon) and their daughters Margaret and Eileen; stepchildren Therese Madden Byrne (Sean) and their children Frances, Evie, and William; Matthew Madden (Francesca) and their children Sofia, Chloe, and Liam; Christopher Madden (Kathryn) and their children Will and Margot; brother Gene O'Brien (Norene); sisters Ellen O'Brien (Tom) Elliott, Mary O'Brien (Tom) Kennelly, and Margaret O'Brien (Jim) Byrne; beloved brothers-in-law Joe Drennan (Susan) and Smokey Stover (Carol); and many beloved nieces and nephews. He was preceded in death by his first wife, Diane Drennan O'Brien (1993); his mother, Mary Frances Sexton O'Brien (1995); his father, Eugene Leo O'Brien, Jr. (1990); and his dear sister, Ann O'Brien Stover (2023). Tom's legacy lives on through his children and grandchildren, who will forever remember his outgoing nature, his ability to connect with everyone he met, his love of celebration and travel, and his lifelong commitment to serving others. In lieu of flowers, the family requests that donations be made to support the Diane O'Brien Breast Cancer Research Fund at Rush University Medical Center. Please send memorial checks, made out to "Rush University Medical Center" to Rush Office of Philanthropy, 28057 Network Place, Chicago, IL 60673-1280 or visit https://rushgiving.com/BreastCancerTribute.
A visitation will be held on Monday, May 12, 2025, from 9-10AM, immediately followed by a funeral Mass at 10AM at Old St. Patrick's Catholic Church, 700 W. Adams St, Chicago. Private Interment.
Arrangements by Sullivan Funeral Home Hinsdale. 630-323-0275 or www.sullivanfuneralhomehinsdale.com