Charles Ergen‘s maneuvering just cost rival SoftBank Corp. 9984.TO -1.82% $1.5 billion by forcing it to raise its offer for Sprint Nextel Corp. S +2.37% But the question remains, is that a victory for the Dish Network Corp. DISH +0.80%chairman, or a defeat?

Mr. Ergen’s knack for being famously hard to read left Wall Street and the telecom industry guessing his next move. Would Mr. Ergen try to convince Sprint shareholders a tie-up with Dish still offers a better deal? Would he sweeten Dish’s bid for Sprint? Would he turn to another telecom target?

Mr. Ergen, who declined to comment through a spokesman, will “go down every path there is” to reinvent his struggling company, whether that involves a deal with Sprint or an arrangement with another telecom company, predicts Carl Vogel, a Dish director and former president.

The stakes are high. Whoever prevails in the deal for Sprint—and at what price—could help reshape a U.S. mobile-phone industry that is increasingly central to how Americans communicate, work and entertain themselves. Dish, meantime, is fighting to remake itself and tap growing demand for wireless broadband service as the pay-TV market stagnates.

Sprint again has recommended to shareholders that they approve the new SoftBank deal, and one of Sprint’s largest shareholders, hedge fund Paulson & Co., which opposed SoftBank’s original bid, said on Monday that it would vote for the higher offer.

“The only way Charlie can succeed is if he wins. There aren’t too many situations where people would get themselves into with Ergen,” said New Street Research analyst Jonathan Chaplin. Mr. Ergen’s reputation “makes it hard for people to partner with him.”

Others say it would be premature to count Mr. Ergen out.

“Typically, he’s looking at big deals that cause his competitors an awful lot of strife by way of [making them] pay more for the ultimate prize, being slowed in their business goals or just having to deal with him as a new competitor,” said Jimmy Schaeffler, chairman of consulting firm the Carmel Group who has known Mr. Ergen for decades.

The khaki-wearing satellite-TV pioneer, 60 years old, has built an empire with a style one of his admirers described as “pencil in the eye” deal making. He has a history of shaking up deals in the works with counter offers and other agitating that often doesn’t lead to an actual deal but nonetheless takes a piece of flesh from competitors.

Mr. Ergen, a one-time professional gambler, doesn’t apologize for the uncertainty. He told The Wall Street Journal last year that he saw business as a card game where he likes to “play the odds.”

In the late 1990s, he stymied an effort by Rupert Murdoch to break into the U.S. satellite-TV business. Three months after Mr. Murdoch’s News Corp NWSA -0.88% . announced plans for a satellite-TV business called Sky, the effort was scuttled in part by Mr. Ergen. His Echostar Communications Corp., Mr. Murdoch’s partner in the venture, filed a $5 billion lawsuit alleging breach of contract. The two sides settled out of court and News Corp. broke into the satellite-TV business with a 40% stake in DirecTV DTV -1.13% . News Corp. owns The Wall Street Journal.

Those close to Mr. Ergen say the strife he causes is intentional—and effective. “Charlie gets a bad rap on his ability to close,” said Mr. Vogel, the Dish director. Dish’s growth “didn’t happen because Charlie wasn’t capable of making deals that made sense for a lot of people.”

Mr. Ergen founded Dish with his wife, Cantey, and a poker buddy in 1980. He and his wife still own a majority stake, and Dish is now the third-biggest pay-TV operator with more than 14 million subscribers.

For years, he kept his full strategy a secret, buying up wireless spectrum and wireless-related businesses without explaining his overall goals for Dish. When pressed by analysts on a conference call in 2011, he said investors would have to “wait and see.”

Mr. Ergen’s recent flurry of attempted deal-making reflects the satellite-TV pioneer’s current quandary: Dish needs to reinvent itself as it faces slowing growth in a mature U.S. pay-TV market. Mr. Ergen now wants to transform Dish into the first nationwide combination of television provider and cellular carrier.Though he owns access to a chunk of the airwaves, that alone isn’t enough to play in the wireless industry.

He has entangled himself with three big players in the telecom industry: Sprint; SoftBank, Japan’s fastest-growing wireless carrier; and Clearwire Corp., CLWR +1.87% which controls valuable access to airwaves that is in short supply. Sprint owns about half of Clearwire and is currently trying to buy the rest.

Mr. Ergen has thrown a wrench into Sprint’s plans for Clearwire and at the same time has tried to woo Sprint away from SoftBank.

Sprint initially offered $2.97 share for the part of Clearwire it doesn’t own and later raised that offer to $3.40 after Dish said it would pay more. Dish then raise its bid to $4.40 in a move analysts say would likely be enough to convince shareholders to vote for that deal.

“I’m not sure what Charlie Ergen wants,” said a Sprint shareholder. “When he raised that bid for Clearwire, it became very unclear. He lost credibility about his intentions toward Sprint.”

On Tuesday, Sprint defended its decision to cut off talks with Dish and move forward with SoftBank. In a public filling, it said Dish failed to deliver a fully baked offer despite numerous meetings and “voluminous” amounts of information provided by Sprint.

A Dish spokesman declined to comment on the filling.

On May 29, Mr. Ergen was huddled in Sprint’s offices in Overland Park, Kan., with executives from Sprint and Dish to exchange financial information as part of deal talks. Soon after the talks wrapped up, Sprint learned from news reports that Mr. Ergen had just raised his bid for a stake in Clearwire, which Sprint had spent months pursuing.

Sprint’s top ranks fumed that Mr. Ergen lobbed the higher bid without giving any notice, according to people familiar with the situation.

—Shalini Ramachandran contributed to this article.

Write to Sharon Terlep at

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