It's an all-too-common story for lottery winners. Months after Kenneth and Connie Parker, who lived in New York state at the time, won a $25-million jackpot, their marriage disintegrated. After Jeffrey Dampier won $20 million in the Illinois State Lottery, he was kidnapped and murdered by his own sister-in-law. And then there's West Virginian Jack Whittaker, who, in 2002, he won $314 million, the largest individual payout in Lotto history.
"I can take the money, I can take this much money and do a lot of good with this much money right now," Whittaker said at the time.
Not quite. Whittaker started out with good intentions, building churches, helping people in need, but the demands for money never stopped.
"It certainly had been a curse to me," Whittaker said. "Before I won the lottery, I thought you could probably control it. Since I won the lottery, I think, there is no control for greed. I think if you have something, there's always someone else that wants it."
Whittaker's marriage fell apart. His granddaughter died of a drug overdose. His daughter died from what is believed to have been a drug overdose.
"If I knew what was going to transpire, honestly, I would have torn the ticket up," said Jewell Whittaker, the lottery winner's ex-wife.
Back in Lakeland, Fla., sheriff's investigators have been tracking Shakespeare's millions. They now believe that he burned through almost $10 million in three years.
Judd said less than $2 million of Shakespeare's money remains. He needed help in managing his newfound fortune, the sheriff said.
"The help -- the person that he thought was ultimately going to help him, the person that convinced him that she was there for his best interests, is Dee Dee," Judd said.
"Dee Dee" is Dee Dee Moore, 37. She befriended Shakespeare a year ago, when his millions were dwindling. She has not been charged with anything in connection with the case but Judd is not shy about saying she is the focus of the investigation of Shakespeare's disappearance and a "person of intense interest."
"Between January of 2009 and April of 2009, she was able to convince him to put all of his known assets, at least to us, in an LLC that she had the ability to cash checks on," Judd said. "The next thing we know, that money disappears from the joint LLC, after she redid the paperwork so he couldn't even cash checks on his own company.
"And she moved that money to her personal accounts and to her nursing staffing agency or medical staffing agency. ... That's what our investigation shows us at this point. And you know what she says? 'Abraham gave it to me as a gift for all the help that I gave him.' Almost $1 million."
Moore's credibility is not helped by a 2001 conviction for insurance fraud and falsely reporting a crime after she falsely accused three Hispanic men of raping her and stealing her car.
Moore now lives in and owns the $1 million home that Shakespeare bought in a gated community on the outskirts of Lakeland.
A call by "Nightline" from an intercom at the gate failed to connect.
But a neighbor who described her house and identified himself only as Justin said, "[There's] a lot of security around the house, lots of cameras."
In a home video posted on YouTube a year ago, Moore coaxes answers from a beleaguered Shakespeare.
"Do you get tired of people asking you for money all the time, Abe? Give me your opinion on that," Moore says in the video.