Stephanie Paula Cummings

Stephanie Paula Cummings passed away peacefully at Pennsylvania Hospital in Philadelphia on Monday, February 16, 2026, surrounded by her husband and sisters. A native Philadelphian at heart, Steph lived a life that carried her across cities, careers, and experiences, yet was always anchored by her love for family, friends, and her hometown, to which she returned in 2019. Steph was born on September 15, 1953 to Mary (Imms) and Aloysius Cummings, the third of seven children.

At the center of Stephanie’s life was her best friend and beloved husband of nearly 50 years, Jim Thompson. They met while teenagers at a high school football game in 1969 but didn’t start dating until 3 years later while working as retail associates at Strawbridge & Clothier (S&C). From that beginning grew an enduring partnership marked by laughter, love, and a shared curiosity about the world. They were married in 1976 and looked forward to celebrating their 50th anniversary in October. Together, Stephanie and Jim built a life rich in friendship and connection, forming a chosen family across the country that held them close—and felt just as deeply held in return.

Steph is survived by her siblings (and spouses); four sisters, Maureen Runge (Dale), Kate Cummings-Judge (Mike), Eileen Taglialatela (Gary-deceased) and Clare Courduff (Edward); and her two brothers, Al Cummings and Jim Cummings (Barbara). Also central to her life were her 16 nieces and nephews and a multitude of great-nieces and nephews, whom she adored and kept close, often traveling with them. She also leaves behind her three beloved cats—Guillermo, Javi, and Luna—cherished members of the household who never had any doubt how completely they were loved.

Born and raised in the West Oak Lane section of Philadelphia, Steph attended St. Benedict’s grade school and then high school at Melrose Academy in Elkins Park. She briefly attended Temple University but left after one semester to help take care of her younger siblings when her mom took ill. She then began working at S&C in Jenkintown which launched her first career in fashion retail. Ultimately, she became a buyer of kids clothing, for companies including Higbee's in Cleveland and Madigan's in Chicago, where she distinguished herself through a keen fashion eye, tremendous work ethic, and a personal style that was unmistakably her own—elegant, thoughtfully accessorized, and always impeccably put together.

In 1989, at the age of 35, Stephanie made a life-changing decision to return to college. While living in Chicago, she earned her undergraduate degree in American History at DePaul University, graduating with an amazing 3.98 GPA. (with her only B in tennis). She had always thought about becoming a lawyer and so she pursued that dream at DePaul Law School. In typical Steph fashion, she earned her J.D. degree and then passed the Illinois bar exam on her first try, becoming an attorney at age 43.

After completing her law degree, Stephanie became an Assistant State’s Attorney in Chicago's family court, where she focused on protecting children and advocating for single mothers, working tirelessly to ensure that families received the financial support they deserved. After she and Jim moved to Connecticut, she continued her work in the Stamford District Court. Her rare combination of integrity, intelligence, and compassion made her a trusted presence in the lives of people who needed her.

Stephanie and Jim shared a love of travel that took them to 49 of the 50 states as well as Canada, Europe and Asia, where they delighted in meeting people, exploring history, and immersing themselves in new cultures. Whether walking the Great Wall of China, exploring the streets of Paris, venturing out in the wee hours to witness the Northern Lights in Alaska or wandering through the maze-like markets of Morocco, Steph approached the world with curiosity and joy.
Steph loved her Philly sports teams. She had multiple sweatshirts and t-shirts for all four professional teams and Temple. You might not be watching a game, but you could still tell how the Philly team was faring, just by listening to Steph’s yells of joy or anguish.

A voracious reader and lifelong student of the liberal arts, Stephanie was never happier than when she had a good book close at hand. She was also, famously, a force to be reckoned with at trivia. Alongside Jim, she regularly competed at Urban Village in their adopted Northern Liberties neighborhood, where her remarkable memory and breadth of knowledge were legendary. One of her final victories came just weeks before her death when she correctly answered the question: “What substance created a flood that killed 21 people in Boston’s North End in 1919?” The answer, which Steph delivered without hesitation: “Molasses!”

A defining characteristic of Stephanie was her sense of fairness and desire to see everyone succeed. She abhorred bullies, especially those who used wealth or power to attack those less fortunate.

And touching every area of Steph’s life, there was her sense of humor – witty, sometimes self-deprecating, always hilarious. She laughed easily, found joy in small moments, and never lost her ability to see the lighter side of life—even in the face of serious illness.

Stephanie's life traced a wide and remarkable arc — outward from Philadelphia across cities, careers, and lives she touched — and finally back home. Those who were lucky enough to have known her are grateful that Philadelphia lent her to the world for a while. We only wish our time together was longer.

A funeral service will be held on Friday, February 27 at Queen of Peace Catholic Church, 820 North Hills Avenue, Ardsley, PA 19038. Family visitation will be from 10:00-11:00am and Mass starting at 11:00am. A celebration of life reception will be held following the Mass.

Stephanie's wishes were that in lieu of flowers, that friends make a donation to the charitable organization of your choice, in her name.