Eddie Lampert, another hedge fund manager who is chairman of Sears Holdings, presided over the merger of Sears, Roebuck and Kmart in 2005. Ackman may have spotted the potential for property sales among the combined company's 3,800 stores.
"He's going to ask Eddie Lampert to step up asset sales and maybe Ackman will ask for a seat on the board," said Scott Rothbort, president of LakeView Asset Management in Millburn, New Jersey.
There have been no big sell-offs announced since the merger was completed in March 2005, but Lampert gained favor at Kmart for making shareholders rich by selling chunks of prime real estate.
"The basic idea is that you can be more aggressive in selling off assets," said Zacks, whose firm sold most of its Sears stock earlier this year as earnings weakened. "It doesn't necessarily help sales but it does help investors."
Despite a recent rally, Sears shares are still down 11 percent this year and same-store sales at both Kmart and Sears, Roebuck have sagged for the past six quarters. In August, Sears Holdings posted a 40 percent drop in quarterly profit.
"Sears and Kmart are in big trouble," said Britt Beemer, chairman of America's Research Group, which surveys consumer behavior. "They have to take a much more aggressive strategy, both in promotions and marketing."
More Marketing Muscle
The company has put more muscle into marketing lately with new campaigns for Kmart and Sears this year. Kmart unveiled new bed and bath products last month, and Sears this week announced the return of its holiday Wish Book after a 14-year absence.
"Sears has been starting to say the right things that make sense from a good retail strategy, but I don't know if it's too late," said Will Ander, senior partner at McMillan/Doolittle, a Chicago retail consulting firm.
Ander says Lampert has delivered the goods for shareholders -- the stock is up at least 14 percent since Sears Holdings began trading in 2005. But cost cuts to buoy profit have not helped store sales, as Sears has lost ground to rivals who are stepping up product innovation, he added.
"Sears needs to get relevant again," Ander said. "It needs to take a look and learn from Penney," which has been offering more fashionable merchandise and adding new private brands.
Hoffman Estates, Illinois-based Sears competes with many other chains, including Kohl's Corp in the sale of apparel and Wal-Mart Stores and other discounters in general merchandise. In appliances and tools, it vies with Home Depot and Lowe's Cos .
Amid that competition and softening demand for home goods, sales at stores open at least a year fell 3.8 percent at Kmart and 4.3 percent at Sears during the second quarter. The retailer's suppliers have felt the impact.
"The challenge we have with Sears and the challenge that they have is to grow their business and get more traffic," Jeff Fettig, chairman of number-one appliance maker Whirlpool, said at a Morgan Keegan conference last month.
Whirlpool is the biggest supplier of appliances that are sold under Sears' proprietary Kenmore brand. Fettig said lost appliance market share at Whirlpool had been largely tied to its Kenmore business.
Still, recent Sears efforts have impressed some. LakeView's Rothbort said the presentation in stores "looks a lot nicer" since the Lampert management made merchandise changes.
"You want to invest in Sears for the undervalued balance sheet and the ability of Eddie Lampert to spot opportunities of value," he said.