Holloway had a home in Stephentown, New York for over 30 years, while living at his Florida residence in Tampa. While he was in Tampa on August 31, 2013, 500 + local high school students broke into his New York house and caused damage that Holloway says exceeds $20,000 while throwing a party. In response, Holloway set up a website, www.helpmesave300.com, to reach out to those who caused the damage in a positive way; instead, he received threats from their parents. Six people were arrested September 26, 2013 in connection with the partygoers who trashed the home. In October 2013, the Holloway home sold at foreclosure auction to the Berkshire Bank, which purchased it for $400,000. It was the sole bidder on the property. After the auction, the Albany Times Union reported that Holloway owed Berkshire Bank $1,006,348.80. He had also built up a backlog of unpaid property and school taxes, totaling $45,131.