Chairman and CEO, Warnaco
Beginning as a bra buyer for Macy's and going on to help turn around Max Factor, Wachner made it big in 1986, when she took over apparel company Warnaco in a leveraged buyout of legendary hostility. When Warnaco went public Wachner became the second woman to head a Fortune 500 company. For a few years, Wachner's tough-edged management style seemed to suit the troubled business. Acquiring licenses from the likes of Ralph Lauren, Speedo, Fruit of the Loom and Calvin Klein, the company expanded rapidly; after going public in 1991, its stock went on a nice little ride, peaking in 1998 at about $44. Wachner joined the board of directors at the New York Stock Exchange - and made sure she was amply compensated for her work.
Then cameth the fall. Calvin Klein sued, alleging that Warnaco, which made his eponymous jeans, was degrading the brand by distributing it through discounters. Wachner countersued, and the parties settled after an enthralling fashion throw-down. The SEC became interested in the company's numbers, and charged it with securities fraud. (In the 2004 settlement, Wachner, whose high pay was another source of controversy, gave up her $1.3 million 1998 bonus; the company admitted that it "failed to inform investors that Warnaco had discovered a $145 million inventory overstatement that would require the company to restate and significantly lower its financial results for the prior three years.")
In 2001, an overleveraged and debt-heavy Warnaco, whose stock price had sunk to less than a dollar, filed for bankruptcy. Wachner was gone by November - a career of genuine accomplishment undone by hubris.