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Kentucky by Heart: Dale Woolum exits rocky path to one of positive fulfillment and concern for others


Editor’s note: This is the second of a two-part about William “Dale” Woolum, who until his recent release, spent four decades incarcerated in various prisons, including the Kentucky Penitentiary. Last week’s part one chronicled his time in prison. Part two looks at the challenges of the past and more recently, his striving to become a model citizen going forward.

By Steve Flairty
NKyTribune columnist

It is now easy to see that young Dale Woolum, raised in Barbourville, Kentucky, born on September 5, 1956, was early on headed in the wrong direction. He was raised one of nineteen children in a poor family. He was not close with his coal miner father (who died in 1971), and his mother felt overwhelmed with the pressures of keeping the family from drowning in despair. It didn’t help that she was shot in the shoulder by a neighbor—if not deadly, matters were made worse for all involved. The family struggled, they needed help, and Dale’s personal behavior was bad; it shouldn’t surprise that many of the Woolum children were transferred to foster homes, including Dale.

Images of the tumultuous times are vivid in his memory. “I remember being shuffled from foster home to foster home in my younger years,” he said, “kicking and screaming and being taken to a big car. I learned emotional traits that an adult would have had at that time… anger, hate, rage.”

Though his home could not be construed to be a happy one, young Dale was saddened when away. He recalls a time being at a foster home and, in his mind, “looking in the distance and seeing Mom and Dad’s house though it was eleven to twelve miles away.” He doesn’t remember any of the foster placings being a good fit, though he mentioned living with a constable for a while, and “he was a pretty good guy.”

Before becoming teenagers, his twin brother, Don, and he were sent to Outwood, an institutional home in Dawson Springs. Calling it “more like a hospital,” Dale didn’t adjust well. He didn’t get along with other residents; he was a rowdy sort and suffered physical injuries with his reckless ways.

Dale Woolum with his fiance Tracy Brundege (Photo from Tracy Brundege)

Today, he thinks hard about those dark early days. “Why I did all the dumb stuff I did, I don’t know,” he said. “Perhaps, because I came from a dysfunctional home and wasn’t getting the attention I needed there.” But even when he received some of the good kind of attention from well-meaning sources, Dale noted that he often wouldn’t accept it. He readily admits that “sympathy” could be added to his list of intense emotions in that stage of life.

Dale returned to Barbourville, and his teen years saw more trouble with law authorities. He was sent for a while to Kentucky Village, a reform school. Later, after leaving there, he had a short, ill-advised, and unsuccessful marriage. He would join the U.S. Army, but after what he said was a “mutual” agreement, he was released after a short while because of his inability to adjust.

But people can change for the better, often with behavior tweaks, in time, that accumulatively register in a significant way. Fast forward to Dale’s prison years, written about previously. As mentioned, he often worsened his incarceration situation by his actions. But during one of those times, while transferring from the Kentucky Penitentiary in 1989 and processing into a prison in Florida, something hopeful emerged from an ugly event.

Feeling verbally abused by officers, a psychiatrist he saw afterward somewhat worked to diffuse the incident. Still, during these moments, Dale recalls that he held on to his anger and cursed God. He was placed in a segregated cell, a move he thought grossly unfair. Emotionally distraught, he tried to make sense of the situation.

“As I paced the floor,” he said, “I mumbled, cursing God, and would climb on the top bunk, even though I was in the cell myself, and look out the window and see other inmates and staff going to and from, chatting in what appeared to be a sunny and warm day. I paced the floor four hours, stopping now and then to read some of the Bible, only to curse God again.”

But in the moment of turmoil, he was also pondering the words he received from an inmate in Kentucky before he transferred to Florida. The message was about God, the Bible, and forgiveness, a message that previously had confused and even agitated Dale.

“I slammed my head into the metal window frame just to feel the pain,” he continued. “Something that was real… to feel anything other than the hurt and rage I felt inside. As I paced the floor again, I began shaking and fell to my knees and cried out to God to forgive me. I began crying physical tears for the first time, probably since my childhood. It was like a floodgate was opened and I could see myself for the first time.”

Not long afterward while wearing shackles and cuffs and being transferred to the Florida State Prison, Dale received conciliatory words from an officer he had confronted previously. The officer also shared his religious faith with Dale.

Those experiences, he recognizes today, brought an important sense of self-awareness proving new to his existence. It portended the start of a new life. “Further hardships would allow me to search deeper for answers that I knew were lingering,” he said. “This began my transformation. I allowed myself to become involved in cognitive skills programs as well as various religious programs. Over the remainder of my incarceration in the state of Florida, I thought a lot about that incident.”

Steve Flairty is a teacher, public speaker and an author of seven books: a biography of Kentucky Afield host Tim Farmer and six in the Kentucky’s Everyday Heroes series, including a kids’ version. Steve’s “Kentucky’s Everyday Heroes #5,” was released in 2019. Steve is a senior correspondent for Kentucky Monthly, a weekly NKyTribune columnist and a former member of the Kentucky Humanities Council Speakers Bureau. Contact him at sflairty2001@yahoo.com or visit his Facebook page, “Kentucky in Common: Word Sketches in Tribute.” (Steve’s photo by Connie McDonald)

He returned to Kentucky Penitentiary in July 2001. Altogether, he possessed a clear conduct record of seventeen years. Someone very familiar with Dale’s past noticed a marked change in the long-time inmate when he got back to Eddyville. Bill Cunningham, noted earlier as the prosecutor of Dale’s stabbing case in 1981, was amazed after initially seeing Dale at his worst decades ago. In Bill’s recently published memoir, I was Born When I was Very Young,” he talked about Dale’s change (referring to him as “William”).

“… I began to hear about the new William Woolum,” wrote Bill. “I began to see him from time to time. We became friends. I could tell by looking at him and talking to him, he was a different person. I was impressed and wondered how long it would last. I’ve always been fascinated by bad people who become good people. Not under the heat of revival night conversion, who go back to drinking and debauchery within weeks–but permanently change—a change you can sense down to the bottom of their shoe leather.”

Bill also noted that Dale related the change to him simply, saying only: “I found God.” Not having discussed it in detail, Bill is convinced that actions now define his old friend and make his life a true “feel good” story.

No doubt, Dale’s turnaround is also supported greatly by the long-distance relationship he established in September of 2018 with his fiancé, Tracy Brundege. “We met through a Facebook page a friend had posted for me,” said Dale. “Tracy responded to it, and when I heard her voice and read her sweet messages, I felt right away that God has sent me an angel. She’s been with me through a lot of trials and selfless sacrifices and giving in a profound way that I hadn’t seen even in my own family.”

Besides staying out of trouble and participating in many educational outreach programs offered him within the prison gates, Dale and another inmate partnered to do something to help vulnerable individuals outside their own world. “I wanted to be involved and with something that would have meaning and purpose, so together we wrote by-laws to a project called The Children’s Fund Project. With the help of countless inmates, we raised over $100,000 in cash value to help the sick and needy children throughout western Kentucky and other parts of the state.” Part of the initiative was to make arts and crafts (including a gigantic dollhouse), some of which were sold for use of the fund.

“I seek no glory in the mentioning of these acts of compassion, but do so in an effort to demonstrate that I’m no longer the same ignorant man I once was,” Dale said, “and hopefully, to inspire someone who may be going through that I went through back then, or in my ‘hay days’ of raising hell, that they too can perhaps find meaning and purpose in becoming involved in something constructive and as a means to and end other than a reckless and destructive lifestyle.”

As is often said, people are capable of turning from a rocky path leading to doom and onto a path of positive fulfillment and concern for others. It is difficult. It takes is some support and an unswerving mindset to make it happen. For this man, it appears to be his sincere goal.

“I have done a lot of wrong in my life, and don’t profess that I am innocent of anything that I have been accused of, nor deserving of anything, but have simply asked for mercy based upon the evidence of my changed life,” said Dale. “I feel that I have received what I have by the grace of God—and the state of Kentucky, despite my horrendous past.”

Hang in there, William Dale Woolum… and keep inspiring us!


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