Judith K. Clegern

Judith Katherine Clegern died suddenly Friday, Jan 9, 2026 surrounded by family. After being born with Neuroblastoma cancer, her neonatal surgeon didn't expect her to live, or walk, or have children, so every day of her 50 years was a major miracle. From Volksmarching in Germany, to babysitting in Maryland, to being a dare devil teen in Florida, to coming of age in Texas, Judy saw life as an adventure and the people in her life as treasures. Thirty one years ago, she bought her next miracle into this world, Tisha Clegern. She completed her Associates degree at BCC and began working with students at Hillcrest Educational. She loved the students and would have been a great teacher if her health had permitted. Instead she became an enabling and creative resource for teachers and staff. Because of her ability to see the wonder and value of any person she met, she became "Momma Judy" to a few hundred people.

In 2006 she married Paul Oleskiewicz and together they produced another miracle, Olivia Oleskiewicz. On Jan 2, 2026, Judy went to work but because she wasn't feeling well, drove herself to Fairview ER where she was immediately DX with terminal cancer and admitted to BMC oncology. A week later she passed from this life after being regaled for three final hours with jokes and stories and music by her brothers who made it to her side just in time. Her family and friends wondered how this could have happened so fast: How could we not have known. But Judy was a private person, she knew how to mask her pain with love and humor and she didn't want to ruin her families last Christmas with an unpleasant reality.

She leaves behind her mother, Carol Killian; her daughters Tisha Iris (Alyssa), Olivia Oleskiewicz; her two brothers, James Clegern (Sarah), and David Clegern (Iris); 3 nephews Ben Clegern (Mariah), Daniel Clegern, and Evan Clegern; her best friend, Tresa Devereaux........ and her large adopted family (too many to name but you know who you are and that you were valued and loved).

One of Judy's last wishes was that she could see one more spring. So, a Celebration of Life is scheduled for April 18 at the Hillcrest Academy.

In lieu of flowers please consider a donation to: Berkshire Habitat for Humanity, Berkshire Humane Society, Hillcrest Educational Center, or Soldier On in Pittsfield.