Dermot Edward Fleming

Dermot Edward Fleming passed away November 5, 2026 at his home in Franklin, Wisconsin. Mass of Christian burial will be at St. Francis de Sales catholic church at 148 W Main St., Lake Geneva, WI 53147. Visitation from 9:30 to 10:30. Mass at 10:30 a.m.

Dermot, “Derm” Fleming was born in Chicago November 2, 1932. The family moved to Delavan, Wisconsin, where his father owned and operated a local tavern and gathering spot, the “Club Charming.” Dermot survived polio at 8 or 9 years of age. Derm spoke often and proudly about his adventures with his 7 siblings, including playing baseball in the street outside their childhood home and catching frogs in the pond with his brother. After graduating from Delavan-Darien High School, Dermot attended the University of Wisconsin–Whitewater before earning his dental degree from Loyola University. Derm enjoyed helping his father at the Club Charming when he returned home from school on weekends.

Dermot met his wife, Jean O’Brien, who worked as an office assistant for one of his dental school classmates. It was suggested by the classmate that the two of them go to a formal dance together, and Jean lit up…“would you!?!” Derm didn’t know who paid for the tickets, but he knew he didn’t himself! They had a very dedicated marriage and did everything together before Jean passed away in 2004. When showing his grandchildren photos of Jean, Derm would often remark, “Cute, ain’t she?” Derm and Jean eventually settled down in Lake Geneva, Wisconsin, on a small farm with their four children. Derm and Jean valued family above all else. Jean enjoyed a good dinner party, but Derm stated his favorite part was the aftermath, when the guests were gone and the kids were asleep, he and Jean would wash the dishes together late into the night. Their love was evident in the life they built together.

Derm’s personality was marked by a pervasive and gentle optimism in the midst of circumstances that would un-anchor most of us. He was quiet in a room of people…until you got him rolling! Affectionately, it cannot be overstated that he was a chatterbox, which must have served him exceptionally well as a dentist.

The grandchild of Irish immigrants and 1600s American settlers, Dermot carried a lively torch for storytelling. Derm’s accounts revealed a big heart under his humble demeanor. He would often share about growing up during the Great Depression, serving as a naval dentist in Okinawa, his distant relatives in Ireland, trips to Hayward, Wisconsin, where his family went from camping in tents to building a cabin and – with incredible fondness – the story of welcoming Nora, his only and beloved daughter, into the family. A devoted Catholic his entire life, Dermot prioritized mass on Sundays, meal time with family, and hunting/deer camp with the men in the family each fall. A 5 o’clock Brandy Manhattan “Canuper” was a daily ritual. He was an avid supporter of the Green Bay Packers, and was very excited about the Brewer’s World Series win the week before he died.

Dermot is preceded in passing by his parents Thomas and Margaret Mary Fleming, wife Jean Fleming, siblings Thomas (late Sue) Fleming, Barry (Mary) Fleming, Maeveen (late Richard) Jeffrey, Sheila (Ed) Devine, and Brian Fleming.

Surviving family members are Margaret Mary (late Emil MD) Palowski Md, Nonnita “Nonnie” (late John) Rooney. Children Brendan (Mary) Fleming, Kieran (Anne) Fleming, Colin (Jill) Fleming, Nora (Guy) Blazei. Dermot was a proud grandparent to Audra Fleming, Claire Fleming, Nikolai Fleming, Keelin (Jake) Grenawalt, Brigette Fleming, Reilly (Stuart) Woller, Jake (Josie) Blazei, Ellie (David) McCleary, Peter Fleming, Miles Blazei, Darby Fleming, and Katie Blazei. Great Grandchildren Emilia Grenawalt, Cleo Woller, and Tyler Blazei.

Dermot quietly chose a life of devotion, humble character, and faith. Derm regularly confided to each of his 12 grandchildren that “you are one of my favorite grandsons/daughters.” He would regularly send out handwritten birthday cards to his grandchildren with carefully selected cartoons and tokens from the past. He was the rock of the family. The spiritual legacy of Dermot is largely evident in the thriving lives and close knit connection of his four children and their families. Inclined toward the position of peacemaker, Dermot left a tapestry of people genuinely fond of each other and with solid character in his wake. 

 A graveside service will take place, after Mass at 11:30 a.m. at St Francis De Sales Catholic Cemetery, 6332 Wisconsin 50, Lake Geneva, Wisconsin, where military honors will also be rendered.

He will be remembered with respect, gratitude, and affection by those who knew him.

To post an online condolence to the family please proceed to the bottom of the obituary under Guest Book where you can submit your post.

Derrick Funeral Home of Lake Geneva is honored to be assisting the family.