Obituary
Guest Book
Feb
28
3:00 p.m. - 5:00 p.m.
Cawood Funeral Home Chapel
112 South 21st Street, Middlesboro, KY 40965
Send FlowersBook nearby hotelsFeb
28
5:00 p.m.
Cawood Funeral Home Chapel
112 South 21st Street, Middlesboro, KY 40965
Send FlowersBook nearby hotelsServices provided by
Cawood Funeral Home - MiddlesboroOnly 1 day left for delivery to next service.
Michael Gordon Whitaker, age 59, of Cumberland Gap, TN, passed away peacefully at his home on Wednesday, February 25, 2026. He was born February 27, 1966, the son of Edna and the late Fuller Whitaker.
Michael enjoyed days spent at the lake or the family farm pond, casting a line in the peaceful water, where a tug was met with great excitement of the catch to come. On the weekends he cheered on his beloved Tennessee Volunteers with loyalty and heart. He wore his orange with pride and celebrated every victory like it was personal.
Michael was a man on a mission — determined to convince his family that Bigfoot was not only real, but probably just beyond the tree line. Whether scanning the woods with a knowing grin or sharing his latest “evidence,” he never stopped trying to bring the rest of us along for the adventure.
Now, Michael has “Gone Squatching” — fishing pole in hand — perhaps finally tracking down that elusive legend along the peaceful banks of heaven’s own pond. We imagine him smiling, waiting for a bite, and keeping an eye out for large footprints nearby.
Michael is preceded in death by his father, Fuller Whitaker.
Left to cherish his memory are his wife, Kristen Whitaker; children, Mary (Dalton) Whitaker, John Michael Whitaker, Michelle (David) Gilbert, Stephanie (Malike) Whitaker, Brooklynn Whitaker and Hunter Whitaker; grandchildren, Bradley, Erin, Eleanor, Ayden, Cheyanne, Josiah and Bryson; mother, Edna Whitaker; siblings, “HF” (Diane) Whitaker, Mary Whitaker and John (Tami) Whitaker; and a host of nieces, nephews, other family and special friends.
The family of Michael Gordon Whitaker will receive friends on Saturday, February 28, 2026, from 3:00 p.m. until 5:00 p.m. at the Cawood Funeral Home Chapel, Middlesboro, KY. Funeral services will follow at 5:00 p.m. with Reverend Keith Medley presiding. Music will be provided by Dakota and Kendra Heck.
Interment will be private.
In lieu of flowers, the family asks that donations be made to the RoHo Charitable Trust.
Online condolences and register book are available at www.cawoodfh.com.
All arrangements for Michael Gordon Whitaker are under the care of Cawood Funeral Home, Middlesboro, KY.
To plant trees in memory, please visit the Sympathy Store.
112 South 21st Street, Middlesboro, KY 40965

What kind of arrangement is appropriate, where should you send it, and when should you send an alternative?
Read more
We'll help you find the right words to comfort your family member or loved one during this difficult time.
Read more
Information and advice to help you cope with the death of someone important to you.
Read moreIf you’re in charge of handling the affairs for a recently deceased loved one, this guide offers a helpful checklist.
Read more
Legacy's Linnea Crowther discusses how families talk about causes of death in the obituaries they write.
Read more
You may find these well-written obituary examples helpful as you write about your own family.
Read more
These free blank templates make writing an obituary faster and easier.
Read more
Some basic help and starters when you have to write a tribute to someone you love.
Read moreFeb
28
3:00 p.m. - 5:00 p.m.
Cawood Funeral Home Chapel
112 South 21st Street, Middlesboro, KY 40965
Send FlowersBook nearby hotelsFeb
28
5:00 p.m.
Cawood Funeral Home Chapel
112 South 21st Street, Middlesboro, KY 40965
Send FlowersBook nearby hotelsServices provided by
Cawood Funeral Home - MiddlesboroOnly 1 day left for delivery to next service.