Five years ago on Christmas Day, Jack Whittaker won what at the time was the biggest Powerball jackpot in history...more than 300 million dollars.
But now, on the heels of the latest lawsuit filed against him: he says he would give it all back.
We sat down with Whittaker in a one on one exclusive...and what emerged was the private side of a man whose life has been very public.
The cases against Whittaker in court read like a laundry list of dirty deeds, which include sexual harassment, assault, DUI and most recently, wrongful death. Now, he wants to come clean.
Whittaker says, "I just go from day to day. Right now, I'm involved in several lawsuits. People sue me for anything."
On Wednesday, Whittaker settled his latest lawsuit...bringing the case and the emotional rollercoaster to an end.
James Tribble filed a civil suit against Whittaker, claiming he funded the drug addiction that killed his teenage son Jesse. Whittaker's granddaughter Brandi Bragg was close with Jesse. The two shared a friendship and a deadly habit. Just months after Jesse died of an overdose in Whittaker’s home...Brandi was gone too.
Whittaker says the loss of his granddaughter leaves a hole in his heart, and nothing can ever fill it. Just the mention of Brandi's name brings tears and regret. "She was my world and I wouldn't trade all the money in the world for her."
What he would trade is his Powerball win.
"The lesson I've learned is not try to do so much for people. I have given 50 million dollars away...and I mean the money keeps coming back to me because I'm a hard worker."
Whittaker says that work ethic is going strong. He owns 43 companies. Whittaker denies reports that claim he couldn't settle other ongoing lawsuits because he's run out of money. He says, "My yearly cash flow from those is about 40 million dollars. I don't think I'm broke. I never said I was broke."
For Jack Whittaker - the winner of one of the biggest Powerball jackpots in history - the only thing that's broken is his heart.