Wilcox was plagued with financial troubles in the 1950s and 1960s. He missed an early opportunity to invest in television; Anna Neagle's chain of dancing schools failed; he and Neagle invested heavily in British Lion shares and the company went into receivership; he borrowed £341,000 from the Edgware Trust; he and Neagle had guaranteed a £75,000 loan to make the two Errol Flynn films; and he paid £100,000 to Terence Rattigan for the film rights to his play "Ross" only for him to be unable to get it made. His film company failed in the 1960s. He spent two years trying to make a film about King Edward VII but the Queen refused permission. He was declared bankrupt in 1964, owing £16,000 to the Edgware Trust and £134,313 over all.