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Kentucky by Heart: After more than 40 years behind bars, Dale Woolum embraces his second chance

First of two parts

William “Dale” Woolum has spent most of his 65 years on earth in prison, most of them at the Kentucky Penitentiary, in Eddyville. While imprisoned there in 1981, he was prosecuted and convicted after stabbing a fellow inmate to death. In December 2021, Dale was released from a federal prison in Allenwood, Pennsylvania, and is now a free man. Ironically, his prosecutor for the stabbing crime acted as a strong advocate for his release.

Dale believes he is a different and better man today, and it started in prison when he developed better habits that would keep him out of trouble, starting with a sincere sense of humility.

“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.”

William “Dale” Woolum (Photo by Tracy Brundege)

But there is a long and often chilling story that happened before gaining the freedom he holds dearly today.

Dale was initially incarcerated in 1978 in the Kentucky State Reformatory, at LaGrange. His crime conviction was for two counts of armed robbery of two liquor stores in Lexington. Behind bars, he soon established a propensity for making already bad matters worse. An example is what happened while at LaGrange. “I took two guards hostage there, at gunpoint, and locked them into one of the open bay wings in Dorm #6,” he said. “As a result of that, I turned my two ten-year sentences into an additional six years for a total of twenty-six years.” The two terms ran consecutively.

In the attempted escape at LaGrange, Dale incurred three charges: attempted escape, kidnapping (later changed to “unlawful restraining”), and possession of a dangerous weapon or contraband. Next stop, Eddyville and the Kentucky Penitentiary.

There, in 1981, Dale killed a fellow inmate, Lester Roades, stabbing him 52 times while the two were on the prison grounds. In the trial, Dale attempted to make the case that he did the act in self-defense after Roades initially attacked him with a knife earlier in the day. The prosecutor, Bill Cunningham, offered a possible ten-year sentence for him to plead guilty, but Dale refused. He was convicted and received a life sentence and five years for the knife murder and promoting contraband. Things got even worse soon afterward at Eddyville when Dale took a prison officer hostage using a fake gun made of soap. For that action, he was moved to a federal correction institute in Terre Haute, Indiana, but after authorities ruled that his accumulated “point custody” required stronger measures, he would be moved again.

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)

“I was sent to Leavenworth, Kansas, where I got in a stabbing case before making it out of the ‘fish tank,’ which is orientation. Although they didn’t charge me (in) outside court,” he explained, “they found me guilty in the institution’s court call proceedings. (For that) I was being sent to Marion, Illinois.” He stayed there for about six months, then was transferred in 1983 to the Kentucky Penitentiary and placed in the lockup unit often referred to as “Maggie’s.”

Dale remained an inmate at Eddyville until 1989 and then was sent to the state of Florida under an “interstate corrections compact,” staying until July 2001 when he again returned to Eddyville. By now, he related, he had “seventeen and a half years of clear conduct under my belt.” Warden Phil Parker, who was previously the negotiator as a beginning correctional officer during Dale’s hostage-taking crime at Eddyville, still felt a need to carefully watch over the inmate he’d long known. Parker seemed reassured and with his influence, Dale received some, at least, mixed news in September 2016.

He was paroled by the State of Kentucky by virtue of good conduct and demonstration of rehabilitative change. Regretfully, however, there was the matter of another conviction to be served in a federal correctional institution he received in 1984 while in state custody — an issue that, compared to his previous offenses seems minor today. Dale was sentenced to two five-year terms, a total of ten years for “aiding and abetting to defraud the United States” for altering two one-dollar postal money orders to show a total of $892.

With the help of a couple of former wardens who knew Dale and former Kentucky Supreme Court Justice Bill Cunningham, Dale served five years at federal institutions and exhibited good behavior, resulting in his recent release where he will serve the remaining five years under federal parole supervision. Today, he lives in an apartment in Lexington and looks forward to a bright and less conflicted future.

I believe the just shared chronology of events about Dale’s brushes with the law and consequences have an almost abstract tone to them. Perhaps the more compelling story is Dale’s past, starting with his difficult childhood in Barbourville and the forces that have brought him to a better place today.

To be continued. Part two next Tuesday

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