"We're just bitterly disappointed this one wasn't going to get to the finish line," said Chief Operating Officer Patrick M. Walsh, after announcing a ninth and final failed attempt to get preferred shareholder approval for the deal. The deal fell apart when New York financier Alden Global Capital reconsidered its preliminary pledge to provide $90 million to help carry out the buyout of shareholders at $2.40 a share, Emmis said. "Despite several weeks of continuing talks, Alden refuses to honor the commitment they made" to help finance the deal, Emmis said. Smulyan, who founded Emmis in 1980 and sold shares on Wall Street in 1994, was trying to once again take it private through an entity he set up called JS Acquisition. The company said it, Smulyan and JS Acquisition "will explore various legal remedies related to damages caused by Alden's actions." Walsh wouldn't expound on what those legal actions could be. He said Smulyan and supporters had little option but to give up their efforts because Alden "had a blocking position" in the deal. It controlled financing needed to sweeten the proposal for a group of recalcitrant preferred shareholders who control 38 percent of preferred shares, more than enough to prevent Smulyan from gaining the two-thirds majority needed to approve the deal. Common shareholders supported the plan. Alden, a hedge fund that specializes in buying corporate distressed debt in hard-hit media companies, didn't respond to requests for comment left with its managing director, Eli Combs. Mark Foster, chief investment officer for Kirr Marbach & Co. in Columbus, said Emmis' future options are limited by a low stock price and heavy debt, which runs 13 times its earnings. "That's high," he said. "This is a business that doesn't have a lot of wiggle room. They're going to have to throttle back growth, generate cash and cut debt." Emmis has struggled with declining profits in recent years due to falling advertising revenues from its 23 radio stations and various city and regional monthly magazines. The stock lost a fourth of its value in over-the-counter trading Thursday, dropping 42 cents after investors heard the buyout offer had fallen apart. That cut the company's market capitalization value to about $46 million.