 In the Black Monday stock market crash of 1987, he reportedly lost $10 million, with a total of $50 million reportedly lost in 1987–1988.In 1990 his firm settled investor complaints of his failure to follow his own rules, for over $2.5 million, without admitting or denying any wrongdoing.He also managed funds for some time in the mid and late 1990s, closing these operations after losses in the summer of 2000.