SINGAPORE: Osceola was one of the greatest Native American leaders of all time, leading his Seminole warriors in Florida to victory against five U.S. generals before finally being captured in 1837, duped under a flag of truce.

Today, one of his descendents, Max Osceola Jr., is carrying on the struggle to secure the future of the Seminole tribe - from a boardroom.

As one of five elected members of the Tribal Council that governs the 3,320 Seminoles, a position he has held for 24 years, Osceola, 57, has played a major role in making the Native American tribe one of the richest in the United States, thanks largely to a well-managed gambling business that has helped build roads, schools and other infrastructure improvements.

Though the tribe does not divulge its gambling revenue, analysts say they believe that it operates one of the most profitable gambling enterprises in the world. According to a report on Native American gambling by Alan Meister, an economist at Analysis Group, total revenue at all of Floridas Native American-owned gambling facilities was estimated at $1.6 billion in 2006. All but one of the casinos are owned by the Seminoles.

In December 2006, the Tribal Council decided to pay $985 million to acquire Hard Rock International, the company that owns the rights to the Hard Rock Cafe brand and several properties. James Allen, chief executive of the Seminole gambling operations, said Osceola was an early and great supporter of the acquisition. “He saw the vision and opportunities for the future,” Allen said.

Osceola sees the business ventures as accomplishing a greater good. “This tribe has gone from being dependent on government contracts, grants and hand-outs to being independent,” he said.

Hard Rock International no longer releases its financial results to the public, but the last published figures, in 2006, showed revenue of $502 million, up 11 percent from the previous year. The bulk of revenue came from the company-owned Hard Rock Cafe restaurants and bars. Operating profit for 2006 stood at $74.8 million, up 19 percent from the previous year.

The acquisition made sense for the tribe in two ways, Osceola said. The Seminoles were familiar with the brand through the Hard Rock Hotels Casinos on their Florida reservations, and buying a broader hospitality business would allowed the tribe to diversify away from pure gambling. While the Seminoles have interests in cattle ranching, citrus production, tourism promotion, sports management and tobacco sales, gambling brings in about 90 percent of tribal revenue.

The Seminoles have big ambitions for the Hard Rock brand. They have already announced plans to develop a Hard Rock Hotel in Penang, Malaysia, and another in Singapore as part of an integrated resort being built on Sentosa Island.

“Over the next 5 to 10 years, were looking to expand the brand from 124 cafйs to 200, the hotels from 9 to 40 and the casinos from 4 to 20,” Osceola said recently at the Hard Rock Cafe in Singapore, where he was meeting with franchisees and scouting for expansion opportunities in Asia.

Analysts are cautiously optimistic about the plans. “Hard Rock has never been really active in the gaming side in Asia, and they have never been a serious casino operator,” said Gabriel Chan, an Asian gambling industry analyst at Credit Suisse. “I think there will be lots of co-branding opportunities.”

A passionate owner and rider of Triumph and Harley-Davidson motorcycles - “I was born to be wild, before we got to rock,” he said with a laugh - Osceola says his other passion is education, which he sees as the key to economic independence for his people.

The second Seminole to graduate from college - from the University of Miami, in 1974, with a degree in political science - Osceola took his first job with the tribe as education director. Today, about 150 Seminoles have gone on to universities and graduate schools, and the numbers are growing, Osceola said.

The Tribal Council has also set up a three-year apprenticeship program for youngsters wanting to learn about the gambling business.

“In our culture, the elders are teachers,” Osceola said.

“Back in the Everglades, they would teach us where to hunt and fish, where to plant. They knew the rhythms of nature. Today, its a different commodity. Instead of fruits and vegetables, its money, and we have to learn how to manage this commodity.”

Edward Lampert, the billionaire financier and chairman of Sears Holding, is fond of saying that a company must be regularly “pruned,” like a tree or a wardrobe. But “you cant cut your way to success,” he warned investors in his annual letter this year.

Now Wall Street wonders whether Lampert had ignored his own advice.

Sears Holding, owner of the Sears and Kmart chains, said Thursday that profit for the third quarter plunged a startling 99 percent, from $196 million last year to just $2 million, as customers flocked to rival stores during the back-to-school shopping season.

Anxious investors punished Sears stock, sending it down $12.25 a share, or 11 percent.

The dismal performance reignited a long-simmering debate over the companys cost-cutting strategy for the two historic retail brands, which have struggled since Lampert merged them in 2005.

Sears said a one-time gain of $101 million elevated its results for the same period a year ago, and made this quarters numbers pale in comparison. The company also blamed factors outside its control, like warm weather, a weak housing market and stiff retail competition.

But frustrated analysts pointed to what they saw as a bigger problem inside Sears: an unwillingness to invest in aging Sears and Kmart stores, which has left the two chains unable to compete with chains like Wal-Mart, Target, Home Depot and Lowes.

“Taking too much cash out of the company and away from the consumer has caught up with Sears,” said Burt Flickinger, a retail consultant, who called Sears “a ticking time bomb.”

From the start, Lampert has cut or restricted spending in areas like marketing and information technology, which the retail industry considers indispensable, as he sought to create a leaner, more profitable business, analysts said.

But the result, Flickinger said, is ragged-looking stores whose shelves are at times bare of essential products, like ketchup and mustard during the height of the summer barbecue season.

Even those who support Lamperts vision of pumping up profits at the expense of sales were left exasperated Thursday. “It was a disastrous quarter,” said Bill Dreher, a retail analyst at Deutsche Bank Securities. “I am not pleased.”

During the quarter ending Nov. 3, sales at Sears Holding fell 3 percent, to $11.5 billion, from $11.9 billion a year ago. Sales at stores open at least a year, a crucial yardstick in retailing, fell 4.2 percent at Sears and 5 percent at Kmart.

Income dropped to 1 cent a share, from $1.27 a share.

“We are very disappointed in our performance,” the chief executive of Sears, Aylwin Lewis, said in a statement, adding that the company could not blame its troubles on the economy alone. “We have much on which to improve.”

The merger of Kmart and Sears three years ago was heralded as an inventive move by Lampert, widely considered a brilliant hedge fund manager.

Lampert vowed to resuscitate the ailing chains by giving Kmart some popular Sears brands like Craftsman and Kenmore and turning hundreds of outdated Kmarts into more-polished Sears stores. He moved away from deep discounts, preferring to sell merchandise at full price.

Much as planned, the combined company became more profitable for a while. Sears Holdings earnings per share rose from $5.59 in 2005 to $9.57 last year. Lampert and the rest of Sears management expressed approval of the new, leaner companies.

But consumers were not as enthusiastic. Sales at stores open a year had been falling before the merger; Lampert managed to slow that trend but not stop it. Less advertising, higher prices and few new stores left Sears and Kmart vulnerable to competitors who aggressively invested in their business.

November 13, 2007 — The hedge fund at the center of Overstock.com’s controversial short-selling lawsuit has filed a counterclaim against the online retailer, arguing it is trying to cover up questionable accounting and poor business decisions.

In a complaint filed late Friday, Copper River Partners alleges Overstock engaged in a multi-year attempt to inflate its stock price via grandiose claims and suspicious accounting.

In August 2005, Overstock sued Copper River, then known as Rocker Partners, and independent research shop Gradient Analytics, alleging the two, in conjunction with a group of regulators and financial journalists, were doing the bidding of a shadowy “Sith Lord” who profited from abusive short sales.

Larkspur, Calif.-based Copper River, which denies those claims, said Overstock’s allegations led to numerous “short squeezes,” or manipulative, artificially induced spikes in Overstock’s shares that were allegedly part of “a campaign of menace” designed to distract from the company’s weak financial performance.

The Copper River complaint focuses on a key shift in Overstock’s accounting strategy that it claims sharply boosted revenues despite no apparent increase in business activity.

The claim also alleges that Overstock Chief Executive Patrick Byrne engaged in a long-running pattern of publicly playing down the retailer’s need for capital.

Overstock’s lawyer, Jonathan E. Johnson, said, “[Copper River] has threatened to launch this since day one, but now it arrives it contains nothing but smoke. The fact that they did not submit it until all other avenues were exhausted speaks to the weakness of their claims.”

roddy.boyd@nypost.com