 At the time, First Executive was the biggest insurer ever to fail, which resulted primarily from money-losing investments in junk bonds.First Executive through Fred Carr had a strong association with Mike Milken and the brokerage firm Drexel Burnham Lambert, whereby at the end of 1990 the company-owned high-yield debt, much of it issued through Drexel, with a carrying value of $9 billion.According to Robert Sobel, First Executive was involved in 90% of Drexel's underwritings, which accounted for about $40 billion in bonds from 1982 to 1987.