June 26, 1946 – February 15, 2026
Obituary
Dennis Fay Jennings, a loving and cherished friend, brother, and uncle passed away peacefully in Oregon after battling health challenges.
Born on June 26, 1946, in Oakland, California, Dennis spent his youth in Palestine, Illinois with his mother, Retha (McDaniel) Jennings, father Benjamin Fay Jennings and siblings James, Robert and Martrene.
His life was a testament of kindness and care. His adult journey began at Eastern Illinois University, earning a B.S. in English, History and Latin and went on to earn a M.Div focused on Urban Community Ministry at the Garrett Theological Seminary at Northwestern University.
After graduate school, his work involved travel across the country and around the world. He worked on several Human Development Projects with the Institute of Cultural Affairs (ICA) in the US and India for 3 years. As staff of ICA he helped create and build the Technology of Participation (ToP) facilitation training in the US. After leaving the staff in 2006, Dennis continued to facilitate and train ToP methods – but this time he started his own business in association with his dear friend and colleague Judy Weddle. For 20 years their practice provided clear guidance to groups in organizations, businesses and communities. They worked in the USA, France, Scotland, Thailand, Singapore, and Malaysia.
Dennis lived in Chicago’s Uptown neighborhood for 40+ years and was a cherished member of the GreenRise intentional living community. He loved walking to get coffee and pastries in the local bakeries on Argyle Street and to Wrigley Field to have a dog at Byron’s and then watch his beloved Cubbies.
Dennis was renowned for his inherently kind disposition, mellow voice and infectious warmth that created a “Mr. Rogers” sense of safety wherever he would go. While our hearts ache with his absence, we will remember him not with sorrow, but with his perfectly delivered wit and humor and kind heart. Dennis knew how to intuitively share the smallest thoughtful action, gift, or comment that would just make peoples’ day. We will remember the many memories of his clear facilitation and patient training, connections to friends and neighbors, and generous contributions to communities. Dennis’ final contributions to the ToP Network were to help assure others continue learning, teaching and practicing the ToP Facilitation and Planning Methods that he loved and with which he was so grounded.
*****
I don’t have words for the depth of loss that I feel. No one knew him better than Judy Weddle, his training partner and close friend. His kindness was as deep as the ocean. The world is not the same without him. His quiet power will be deeply missed. May he Rest in Power, Love to all,
~~ Cheryl Kartes
The only thing that I would add was Dennis’ connection to Uptown. He was one of the first residents of uptown that joined in wholeheartedly with the work of the ICA. I was on the uptown team and he and I would walk the streets of uptown together, delivering flyers trying to get people to come to meetings, etc. He was definitely someone who loved the grass roots and knew the importance of their input into any plan.
Two memories of Dennis (maybe happened, maybe invented)
Dennis embodied a quiet leadership, truly demonstrating that leadership does not need to come from knowing the answers but from observing, holding space, asking questions, and showing up. I was lucky to start my facilitation journey in Chicago, where I was mentored by and shared community with Dennis.
He led by example in everyday expressions of care – he shepherded the GreenRise community in recycling and keeping the kitchen clean; showed up as a participant and friend to meetings, shows, performances, etc.; and generously shared his wisdom and time with the next generation of facilitators and celebrated us as we advanced in our journeys. I am grateful for his being 
~~ Samantha Sainsbury
I didn’t know Dennis very well, except by reputation. Linda knew him better I think because of her being more active in ToP training. But it just occurred to me to comment on the blessings we all have as we are making our own preparations to follow the way Dennis and so many of us are going. As those who knew Dennis well are expressing their feelings of grieving and appreciation, it is worth mentioning what a privilege it has been and is to be a part of this “beloved community” with the common memory that is embedded in us. With gratitude for Dennis and you all.
~~ Milan Hamilton
There isn’t a bad thing anyone in this world could say about Dennis. He was simply the best. Loving, nurturing, kind, thoughtful, funny, and just filled with so much care and dedication for the people and spaces around him. Dennis will be so dearlymissed by so many. His presence in our community and lives will never be quite filled – but may we be able to take the wisdom and care he imparted on us into all the rooms we step into — and make each space a little better for it. May we be able to embody his humility, soft-but-grounded presence, and quick wit and levity. Dennis had a great quiet knowing: he knew what was needed to make any situation better, and had a way of manifesting what was needed.
I know many of our hearts are broken by this huge loss – and we will find a time to grieve and celebrate this cherished and wonderful life in community soon. For now, here are some words from his partner in crime, and the one who knew him best,
~~ Judy Weddle
While Dennis was a quiet and careful person, he exhibited many strengths. He soared when recalling data gleaned from research. He was thorough and trustworthy in reporting data. There was many a time in meetings when the group would become silent when he would speak up – knowing that his contribution was valuable and that he was going to make was succinct comment that was thought-through and nearly always a helpful perspective – either with new ideas keenly analyzed or accurate reflection of contributions from chaotic conversations. He was an especially organized person and could “pull up” and find facts that would be long past for many of us.
Dennis had a gift for planning paying careful attention to details. This made him a powerful facilitator. He loved the Technology of Participation and was totally grounded in these methods. He enjoyed leading groups and helping people find meaning from the work they do. He also enjoyed ToP Training and teaching the methods to others. We have lost an example of fine facilitation and training support. Dennis was proud to have been a part of the Institute of Cultural Affairs for many years. He was a part of the staff for many years.
Dennis was also a very kind and gentle person. His spiritual foundations made his personal values strong. He knew how to live in community. He was not weak. He was tenacious and rooted like a tree. While he did not relish conflict he did not run from it. He would throw himself into the fray, even knowing how stressful it was for him, whenever he felt the need to stand his ground. He cared deeply for others and he had a self-deprecating sense of humor that many people admired. My sweet friend. I will miss him.
~~ Seva Gandhi
I only met Dennis a few times, but his gentleness and smile have remained with me. I also remember that Dennis and Joyce Reese worked as a team in and around Chicago.
~~ Nancy Lanphear
When I heard the news about Dennis, a flood of memories came rushing back….work groups in the ICA GreenRise in Chicago, trainer gatherings in Phoenix in the early years of the ToP program, my CTF assessment (he was one of my assessors)…the list is long. He was kind, smart, gentle, wise, and funny. He was not always the first to speak, but many times the last, because often what he said just made so much sense. When I think of the embodiment of the values of ToP, I will always think of Dennis Jennings. This void hurts, even as we celebrate his completed life. Well done, good and faithful servant.
~~ Deb Burnight
Dennis was a very special human being. One of the most memorable Thanksgiving’s I have ever had was in a tiny village, Jawale, India. I was there working on a women’s village program in 10 villages around Jawale. Before Thanksgiving. Dennis was headed to Pune the nearest big city and when he returned in the evening, he brought with him the makings of a Thanksgiving feast, freshly baked dinner rolls and slices of ham. After a full day of work, a few of us joined him in his small little place, singing Thanksgiving songs we could remember to acknowledge the celebration of Thanksgiving.
When we both returned to the US, we ended up living in the ICA on the seventh floor. My little daughters found out they loved to go down the hall and let Dennis read to them. They would pick out a book and sit mesmerized as he introduced them to great children’s stories.
One time in the late 90s, we were both working on the first floor of that same building and I approached his desk first thing in the morning as he arrived to begin his day. He slid open his drawer, pulled out his glasses repair kit, tightened the screws on the earpieces, and then shine them up for the day. He then remarked I do this every morning so I know I’m ready to take on all the day has to offer.
He was a gentle, caring human being, and a dear friend of 50 years. Dennis, I’m grateful for the gift you were to me, to my children and to the communities and people that you served. In gratitude,
~~ Paula Philbrook