During a season when most homes are preparing for celebration, others are quietly preparing their hearts for a different kind of holiday — one shaped by loss, memory, and the ongoing journey of healing. In this special conversation, I sat down with two generations of the Calahan family — Mrs. Shirley Calahan, Mr. Ed Calahan, and their daughter, President Valerie Calahan Taylor — the Chicago-based family behind Calahan Funeral Homes, a longstanding pillar of compassion and service.
What began as a simple interview quickly unfolded into a deeply personal look at how this family has served Chicago for decades, not just through loss, but through legacy-building and community care.
Growing Up in the Family Business
When I asked Valerie how she found her way into the funeral profession, she smiled with a familiarity that only comes from real life experience. For her, the funeral home was not a place of fear — it was home.
Birthday parties, sleepovers, family moments — all happened upstairs, just above the rooms where her parents comforted grieving families. After college, despite opportunities elsewhere, Valerie chose to bring her passion for marketing back to her family’s legacy. “It was always normal to me,” she shared. “I wanted to use my gifts to grow what my parents built.”
A Love Story Rooted in Service
Mr. and Mrs. Calahan have been married 45 years, and their story is as intertwined with the funeral home as the families they serve. Mrs. Calahan went back to school to become certified after falling in love with the man who had already fallen in love with this ministry of care. That decision would shape the trajectory of their family and the thousands of Chicagoans they have comforted across generations.
Caring for Families, Not Just Funerals
As the holidays approach, the Calahans know the weight that many families carry. “Grief feels different this time of year,” they shared. “People are trying to celebrate while feeling the absence of the person they love.”
To meet that need, Calahan Funeral Home offers something rare: a three-year support program for families after a loved one transitions. Their annual events bring families back together to receive comfort, community, and tangible support.
And through the Calahan Foundation, they’ve given back more than $400,000 in scholarships, turning grief into opportunities for young people to rise.
A Legacy of Dr. Dennis Deer through the Love of Mrs. Barbara Deer
We were joined by Mrs. Barbara Deer, widow of the late Dr. Dennis Deer, former Cook County Commissioner and a beloved Chicago figure who passed away 17 months ago.
Their story reads like a love letter to Black excellence and commitment:
High school sweethearts.
College partners.
Three children executing life with excellence
A one-year-old grandbaby he did not get to meet but lives through daily
And a legacy that continues to serve Chicago.
Mrs. Deer spoke with grace about navigating her second holiday season without him. She makes sure there is Banana pudding on the table, his favorite dessert. That has become a way to keep him at the table, even in spirit. His memory lives on not only in his family, but in the Dr. Dennis Deer Community Justice Center on the West Side, serving youth and families daily. She said driving past it brings a level of comfort: “His name will always be remembered.”
He was also a proud member of Omega Psi Phi Fraternity, another community touched deeply by his passing.
Advice for Those Facing Their First Holiday Without a Loved One
Both the Calahans and Mrs. Deer offered heartfelt encouragement to families moving through grief this season:
• Talk about your loved one. Share the stories, say their name, keep their presence alive.
• Cook their favorite foods. Eating the meals they enjoyed brings connection and comfort.
• Do not run from the moment. Lean in. Allow the memories to meet you where you are.
• Know that grief is not a weakness. It is love refusing to disappear.
A Season to Hold Each Other Close
Chicago is a city built on family, tradition, and resilience. This conversation was a reminder that while loss may change the holiday table, it does not erase the love, the legacy, or the impact our people leave behind.
And thanks to families like the Calahans — and voices like Mrs. Barbara Deer — we are reminded that healing is possible, hope is available, and no one has to walk this season alone.
