On February 18, 2014, Reynolds was arrested in
Zimbabwe for overstaying his
visa.
He was allegedly found to be in possession of pornographic videos he had filmed with several women at the hotel where he was staying. Possession of pornography is a crime in the country. He had also purportedly accrued over $24,000 in hotel charges that he had yet to pay. The pornography charges were later dropped, but he pleaded guilty to violating immigration laws, and was deported to
South Africa.
He claimed in early March 2014 to be hiding there from Zimbabwean death squads, who he claimed were targeting him because he possessed information about American companies from Chicago doing business illegally in Zimbabwe.
On June 26, 2015, Reynolds was indicted by a grand jury for failure to file federal income tax returns for the 2009 through 2012 tax years on more than $400,000 income. The next month he missed his arraignment, because he could not return to the U.S. due to issues with his daughter's health he claimed. It was not clear where Reynolds was, although he had previously hidden in South Africa out of fear for his life. In April 2016, Reynolds was sentenced to two months of prison for two bond violations in his tax case and his trial was scheduled for September; Reynolds decided to represent himself in court.
[22] Reynolds claims the majority of the income the government claimed should be filed on income tax returns was given by Elzie Higginbottom, the key witness for the trial on misdemeanor tax charges, to him in order to travel to South Africa to set up opportunities in real estate and the diamond industry. On September 28, 2017, Judge
Robert Gettleman found Reynolds guilty on tax charges, on all four counts alleging he failed to file a federal income tax return for four consecutive years. He was sentenced by Gettleman to six months in prison on May 10, 2018 which he begun serving at the
Metropolitan Correctional Center in Chicago on August 1. At a press conference after the sentencing, Reynolds stated he planned to move to South Africa with his daughter after his release.