The story of mergers and acquisitions is filled with ruthless corporate raiders, devastating word wars and people trying to stifle each other.

T. Boone Pickens, an oil tycoon who raged in the 1980s, took small stakes in energy companies, attacked management and forced them to sell. Carl Aikan, an investor activist, was accumulating shares in companies and threatening to dismiss their boards if they did not agree to the deal. And Robert Campo, a Canadian real estate investor known for buying machinery, was not afraid to sue companies seeking to thwart his achievements.

However, even with all these thunderous tactics, the world of deals has never seen a buyer like Elon Musk.

A few weeks after Mr Musk, the world’s richest man, signed a $ 44 billion deal to buy the Twitter social networking service, he turned the landscape of deals upside down. Usually, when the two parties agree to negotiate an acquisition, they spend weeks studying finances and knocking out details. The action takes place mostly behind closed doors, in meeting rooms and in prestigious law firms and investment banks.

But Mr Musk has given up due diligence to make a deal with Twitter, according to legal documents. Since then, he has publicly criticized Twitter – naturally on Twitter – attacked some top executives and posted tweets that mocked the company’s board. And with memes and a poop emojion social media he seemed to be trying to reconsider the deal price.

In fact, the 50-year-old Mr. Musk turned what was largely a friendly deal into a hostile takeover. His actions have led Twitter, regulators, bankers and lawyers to doubt what he can do next and whether the blockbuster deal will be completed. And Mr. Musk has made past corporate raiders look positively quirky compared.

“Elon Musk is playing in his gray zone – you could almost say according to his own rules,” said Robert Wolf, former chairman of the United States for the Swiss bank UBS. “It’s certainly a new way of making deals,” he said.

Mr Musk did not respond to a request for comment.

On Thursday, Twitter executives said at a company meeting that Mr Mask’s purchase was moving forward and that they would not negotiate, according to two participants who spoke on condition of anonymity. Earlier this week, the company’s board also said: “We intend to close the deal and enforce the merger agreement.”

The Twitter board claimed it had a legal advantage in the deal. In addition to the $ 1 billion gap fee, the agreement with Mr. Musk includes a “specific enforcement clause” that gives Twitter the right to sue him and force him to complete or pay the deal as long as he has borrowed corral funding remains intact.

“He has signed an agreement that is binding,” said Mr. Mask Edward Rock, a professor of corporate governance at New York University School of Law. “If these agreements are not enforceable, it is a problem for any other transaction.”

Twitter did not respond to a request for comment.

Mr. Musk has already pushed some legal boundaries. The Federal Trade Commission is investigating whether the billionaire violated the disclosure requirements by not telling the agency that he had amassed a significant stake in Twitter earlier this year, said a man knowledgeable about the investigation. Investors typically have to notify antitrust regulators of the purchase of large shares to give government officials 30 days to review the deal for distortions of competition.

The FTC declined to comment. The Information, a technology information site, previously reported on the FTC’s interest in Mr. Musk.

The archetype of a hired corporate buyer has existed for decades. Jay Gould, a late 19th-century baron-robber who helped build the U.S. rail network, financed the deal in part through wealth accumulated through his gambling on Wall Street. He united the dying railways and was known for spreading rumors in the press.

Mr. Gould, according to one of his biographers, Edward Renehan Jr., was a “margin maestro” who was able to build capital out of thin air and gain control of companies using just a few dollars displayed in the hall of financial mirrors: merry-go-round convertible bond houses. , proxies and cash with loans ”.

In the same decade, Mr. Campo used foreclosures to build a retail empire that included Bloomingdale’s and Abraham & Straus, who eventually perished under the loans he loaded on them. There was also a new type of enemy raiders – private investment firms – who used the captive tactics described in the book Barbarians at the Gate, a 1989 book on the private investment company KKR and its acquisition of RJR Nabisco.

In recent years, deals that have broken up or been re-concluded have not been uncommon. After Sally Mae, a student lending giant, sold herself in 2007 to a consortium of financial firms for $ 25 billion, a credit crunch unfolded and new legislation threatened his finances. Buyers tried to cancel the deal, insults flew, and efforts failed.

That same year, Apollo Global Management’s $ 6.5 billion deal – a merger of the chemical company Hexion, which it owned, with rival Huntsman – collapsed when Huntsman’s revenue fell and each side sued. In 2016, telecommunications giant Verizon lowered its price by $ 4.5 billion for Yahoo’s online business after Yahoo discovered it had suffered a huge security breach.

However, in many of these transactions, the price change or the cessation of the acquisition was due to actual “significant adverse changes” – be it a financial crisis or a breach of security. Now this is not the case with Twitter and Mr. Musk, where no obvious factor has emerged for trying to change the contours of the agreement. (Mr. Musk, who was fascinated by the number of bots on Twitter, said he doubted the veracity of the company’s public statements.)

Mr. Musk seems free to do whatever he pleases, in part because of his extraordinary personal wealth, his net worth is about $ 210 billion, and that allows him to ignore the economics of the deal. And unlike a private investment company, it doesn’t buy multiple state-owned companies a year, making it less important to present itself as a consistent approximator.

Although Mr. Musk is accountable to shareholders of other companies he manages – including the public carmaker Tesla – these shareholders usually invest in his efforts because he is an inventor, not because that he makes deals.

Anne Lipton, a professor of corporate governance at Tulane Law School, said much of what keeps the world of mergers and acquisitions within is “reputational sanctions.” But Mr Musk, she noted, “reputational sanctions don’t matter”.

And that leaves almost everyone guessing.

Mike Isaac and Cecilia Caen contributed to accountability.

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