Van Winkle currently lives in Wellington, Florida with his wife, Laura (whom he married in 1996), and two daughters, Dusti Rain and Keelee Breeze. He had stopped using hard drugs and alcohol in 1994 following his failed suicide attempts, but continued to use marijuana until 2005, when he was informed by his throat doctor that he risked losing his voice if he did not quit.
In January 2001, Van Winkle was arrested by police in Davie, Florida for assaulting his wife. According to the criminal complaint, they got into an argument as they drove on Interstate 595, with Van Winkle allegedly pulling hair from her head. He pleaded guilty to charges of disorderly conduct four months later, and was sentenced to probation and ordered to attend family therapy sessions.
He briefly attracted the attention of the media when his pet wallaroo, Bucky, and pet goat, Pancho, escaped from his Port St. Lucie, Florida home in November 2004. After wandering around local streets for over a week, the animals were caught, and returned to Van Winkle. He had to pay a $220 fine for expired pet tags, and an undisclosed fine for the escape of the animals.
On April 10, 2008, Van Winkle was arrested in Palm Beach County on a battery charge for allegedly kicking and hitting Laura. He was released the following day after Laura declared that her husband had only pushed her. In court, the couple's neighbor, Frank Morales, stated that it was merely a verbal argument. According to the police report, Van Winkle had told police that his wife is bipolar and tends to get irrational and argumentative, despite being on medication. Van Winkle was ordered by a Florida court to stay away from his wife following his arrest, and to only communicate with his children only if Morales accompanied him. The judge told Van Winkle that he could only contact his wife via telephone.
On April 29, 2008, his lawyers, Bradford Cohen and Joseph LoRusso, were able to get the entire case dropped, after providing the state attorney with evidence that conflicted with what was originally reported. Van Winkle released the following statement on his website: "I love my wife and my family. We have been together for fourteen years. Every now and then there is a bump in the road just like in most relationships; unfortunately mine is made public, and the media has a way of twisting things around. Don't believe what you hear. When I got out, we hugged and made up. We just want the whole thing to go away. My family means the world to me, and I would never hurt anyone."