McClendon's proposals have ranged, these people say, from launching a new AEP vehicle to drill shale in parts of the U.S. where it does not now operate, like California, to gathering a pool of permanent capital for him that could be used for more general business purposes. One iteration of the permanent-capital effort—a special-purpose acquisition company, or "SPAC"— intended to raise $200 million, encountered a hiccup in mid-February, these people add, after Citigroup, the key underwriter, abruptly backed away.
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McClendon declined through a spokesman to comment for this article, and EMG representative referred a reporter to prior statements.
In a December interview on CNBC, EMG chief executive John Raymond was upbeat about his investment and the energy markets. His company has invested more than $3 billion in AEP, contingent among other things upon setting up independent oversight for the driller's various projects.
"With respect to the price of oil, it's been a very volatile conversation, so candidly, this is something we live with in our businesses each and every day," Raymond said.
Given the right assets, management and cost structure, he added, an operator "absolutely" could make money in a $50-per-barrel oil market.
People close to AEP and EMG said that deal talks of various stripes were intermittently underway, and that apart from the day-to-day issues of running a business together, the rapport between McClendon and Raymond remained smooth.
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In an indication of EMG's continuing commitment to AEP's drilling efforts in Ohio and West Virginia—an undertaking collectively referred to as AEP Appalachia Holdings—EMG recently invested an additional $150 million in cash, said a person familiar with the transaction. It may soon add the same amount or more, according to that person and others.
Some industry observers said that McClendon's latest financing efforts come as little surprise.
"He has always been remarkable at raising money in up and down markets," said Josh Fershee, who teaches energy and business law at the West Virginia University and has been following McClendon's career closely since 2010. "Long-term, it's always a good play, but the short term, it's risky."
One risk that bettors on McClendon have had to accept is his penchant for leverage, or borrowed capital—a tendency that became uncomfortably public in October 2008, when as CEO of Chesapeake he was forced to sell 33.5 million shares of his own company stock. The sale was motivated by a need to raise cash to meet a personal margin call that hit just as Chesapeake stock was hitting a multiyear low.
Nonetheless, McClendon was wildly successful with Chesapeake, a company he co-founded in 1989 and which grew into the second-largest natural-gas driller in the country. Despite the financial crisis of 2008 and a concurrent plunge in gas prices that forced the company to retrench, McClendon enjoyed a solid 24-year run before stepping down under pressure in 2013, after corporate-governance questions and reports of conflicts of interest came to light.
It was during McClendon's waning months as CEO, when he was preparing to hand the reins to a replacement, that he is now alleged to have stolen Chesapeake trade secrets.
In court papers, Chesapeake describes McClendon as swiping proprietary company land surveys undertaken in 2012 and 2013 to help inform his eventual AEP investments in the Utica shale, investments that Chesapeake says it should be reimbursed for identifying.
McClendon and EMG have said the suit is meritless, and that they intend to file counterclaims.