Brennan was best known for building up the company's massive financial service and real estate operations during his reign as chairman and ceo from 1986 to 1995, only to subsequently shed them to refocus the business on retailing.
He also introduced a "store of the future" program to modernize the fleet, which was considered an innovative strategy in a largely sleepy industry, though the expected sales gains never quite surfaced for Sears.
While Brennan is credited with making bold moves, and was among the nation's most formidable business leaders at a time when Sears was America's top retailer, he was under enormous shareholder pressure for much of his tenure and ultimately, Sears slipped in status. At one time, Sears led all of the nation's retailers in volume, but during the Eighties began to be eclipsed by emerging and nimbler competition, notably Wal-Mart Stores Inc. and Target Corp.
As Sears' retail operations began slowing, Brennan and his team put the emphasis on creating a financial conglomerate, with brands like Dean Witter, Coldwell Banker and Discover. However, in the mid-Nineties, Brennan initiated sell-offs and cost-cutting maneuvers that would return the emphasis to the core Sears Merchandise Group, while reducing debt and the threat of a takeover while satisfying investor demands. The Merchandise Group was refocused into three categories: apparel, home and automotive. In addition, 50,000 jobs were cut and scores of stores were closed.
"He changed the whole approach for the corporation," said retail analyst Walter Loeb. "He was one of the first to renovate the stores and bring new dynamics to them. The stores became more fashionable, more oriented toward women, and he also reemphasized the three major hard goods brands — Diehard, Craftsman and Kenmore."
Loeb credited Brennan with modernizing stores and bringing new ideas to them in the Eighties, including the Cheryl Tiegs celebrity endorsement line and "a completely streamlined merchandising system."
Another source described Brennan as "very much a corporate man," and slow to bring change, though he proved to be the one who moved faster and help speed up Sears' moves more than his predecessors.