Site icon 20/20 Tonight

“Unlucky Numbers”: 20/20 Reports on Abraham Shakespeare Homicide April 18 2025

Ryan Gill

This Friday, April 18, 2025, ABC’s 20/20 presents an all-new two-hour special titled “Unlucky Numbers,” airing from 9:01 to 11:00 p.m. EDT. The episode investigates the astonishing and deeply unsettling case of Abraham Shakespeare, a Florida man who won $30 million in the lottery only to vanish three years later under suspicious circumstances. With exclusive interviews and a rare phone call from the woman convicted of his murder, correspondent Matt Gutman leads viewers through one of the most tragic cautionary tales about sudden wealth.

Featuring firsthand accounts from law enforcement, close friends, and family members, the special unpacks how Shakespeare’s dream win became a nightmare. Interviews include prosecutor Jay Pruner, detectives David Clark and Greg Thomas, author Deborah Mathis, Shakespeare’s cousin Ashley McMillian, and former girlfriend Sentorria Butler. The episode also revisits the efforts of amateur internet sleuths whose findings helped guide investigators toward the truth.

From Modest Beginnings to Lottery Millions

Abraham Shakespeare was born on April 24, 1966, in Lakeland, Florida. A casual laborer and truck driver’s assistant, Shakespeare lived a modest life before his improbable lottery win in November 2006. He purchased the winning ticket through a co-worker during a stop at a Frostproof convenience store and claimed a one-time lump sum of $17 million.

Though Shakespeare bought a home in a gated community and made a few modest purchases, he remained relatively frugal. He used much of his winnings to support friends, family, and even strangers, but soon began expressing regret over the windfall. He reportedly told a friend, “I’d have been better off broke,” as he became increasingly burdened by constant requests for money.

His fortune, once seen as a ticket to freedom, made him vulnerable. In 2008, Dorice “Dee Dee” Moore entered his life under the pretense of writing a book about him. Instead, she quickly assumed control of his financial assets and created a company named Abraham Shakespeare LLC, through which she manipulated access to his remaining funds.

A Disappearance and Mounting Suspicions

By April 2009, Shakespeare was no longer seen by his family or friends. Dorice Moore repeatedly told concerned parties that he had left town to escape the pressure of being a lottery winner. She offered inconsistent accounts of his whereabouts, claiming at various times that he was in Texas, the Caribbean, or sick in a hospital. Meanwhile, she continued to live in his house, send text messages from his phone, and pose as him to avoid suspicion.

Moore’s behavior quickly drew attention. She attempted to pay others to claim responsibility for Shakespeare’s disappearance and even tried to bribe individuals to fabricate evidence of his well-being. Despite these efforts, people close to Shakespeare grew increasingly skeptical. His illiteracy made the grammar in the texts suspect, and friends noticed the inconsistencies in communication. One of his friends, Gregory Smith, began cooperating with police as an informant, providing critical insight into Moore’s deception.

The Grim Discovery and Arrest

On January 27, 2010, investigators uncovered Abraham Shakespeare’s body buried beneath a concrete slab behind a home owned by Moore’s company in Plant City, Florida. He had been shot twice in the chest. Days earlier, Moore had shown Gregory Smith the burial site and handed him the murder weapon in an attempt to frame him for the killing.

Moore was taken into custody shortly after the discovery. She was initially charged as an accessory after the fact but was later indicted for first-degree murder. Prosecutors revealed that she had killed Shakespeare in April 2009, likely after he confronted her about the disappearance of his funds. During the trial, the state presented overwhelming evidence of her manipulation and greed.

Trial, Conviction, and Sentencing

In December 2012, Dorice “Dee Dee” Moore was convicted of first-degree murder. She was sentenced to life in prison without the possibility of parole, with an additional mandatory sentence of 25 years for possession of a firearm during the commission of a felony. Judge Emmett Lamar Battles described the crime as “cold,” “calculated,” and “cruel,” calling Moore the most manipulative person he had ever seen in court.

Since her conviction, Moore has continued to seek a new trial, filing multiple post-conviction motions alleging ineffective counsel and prosecutorial misconduct. Although some claims were allowed to be amended and refiled, most have been dismissed or denied. In 2025, the case remains unresolved in post-conviction proceedings, with a judge expected to rule on Moore’s latest motion.

Web Sleuths and Public Involvement

One of the most remarkable elements of the Shakespeare case was the role played by internet sleuths. Members of the online forum Websleuths tracked real estate records and social media activity that helped investigators identify Moore as a person of interest. Detectives eventually acknowledged the contributions of the amateur sleuths, stating their findings supported and at times exceeded official investigative progress.

Moore herself even joined the forum and posted under a pseudonym, attempting to defend herself and deflect suspicion. Her online interactions, along with other suspicious behavior, helped paint a picture of someone attempting to outwit both authorities and the public.

The Legacy of Abraham Shakespeare

Abraham Shakespeare’s story has become a symbol of the darker side of instant wealth. Despite his generosity, he was ultimately exploited by someone he trusted. His life, and tragic death, serve as a cautionary tale about the dangers of financial vulnerability and the predatory behavior that often surrounds sudden riches.

“Unlucky Numbers” revisits the emotional weight of this case and provides new insights, including an exclusive phone interview with Moore from prison. With testimony from key figures and deeply personal reflections from those who knew Shakespeare best, this 20/20 episode offers a compelling and sobering examination of how a life filled with hope ended in betrayal and tragedy.

More Feature Articles

Exit mobile version