FILE- In this June 14, 2018, file photo, Tesla CEO and founder of the Boring Company Elon Musk speaks at a news conference in Chicago. For years, Tesla’s board remained almost invisible, staying behind the curtain as Musk guided the electric car maker to huge stock price increases. Now, given Musk’s recent questionable behavior, experts say it’s time for the board to step onstage and take action on the company’s leadership. (AP Photo/Kiichiro Sato, File)
INTERNATIONAL - Tesla chief executive Elon Musk's contemplated $72 billion (R1trillion) take-private deal is presenting investment bankers with a dilemma: overlook concerns about how feasible it is or risk missing out on what could be this year's biggest and most high-profile acquisition.

Musk did not just catch investors and analysts off guard earlier this month by announcing on Twitter that he was considering taking the US electric car maker private. He also sent shock waves throughout the investment banking world, which reacted to the news with excitement and bewilderment.

This is because no company of Tesla's size has ever been taken private by financial investors as Musk has suggested, as opposed to being acquired by a bigger company.

Moreover, the standard method of doing so, saddling the company with debt in a so-called leveraged buyout, is not an option for Tesla given that it is already servicing a debt mountain of some $11billion and is not making any money. It reported an operating loss in 2017 of $1.6billion.

Debate over the deal’s feasibility has polarised bankers. During one conference call at an investment bank last week, discussion on whether the deal represented a major opportunity or a fools’ errand degenerated into a shouting match, according to one of the bankers who provided the details on condition that neither he nor the bank, which decided not to pursue a role, are disclosed.

“Given the size of a deal, the company's debt capacity and cash flow, bankers seem similarly chary about this deal happening anytime soon,” said Stefan Selig, a former top Bank of America Corp banker who is the founder of financial and strategic advisory firm BridgePark Advisors LLC, which is not involved in the deal.

Bankers aspiring to advise on the deal are courting Musk and Tesla’s special board committee that will independently consider the merits of Musk’s expected offer.

Working for Musk could also come with reputational risk, given that the US Securities and Exchange Commission is investigating the factual accuracy of his assertion on Twitter that funding for the deal was secured, sources have said.

However, many bankers said this would not be a deterrent given the magnitude of the potential deal.

“That's likely not enough to colour a banker's view on whether or not there is an opportunity,” said Ted Smith, a co-founder and partner of Union Square Advisers, a technology boutique investment bank. Union Square is not trying to win a role in the Tesla deal.

Musk, who owns about a fifth of Tesla, said in a blog post last week that the effective size of the deal would be much smaller than the $72billion equity valuation of his offer, because, according to his estimate, two-thirds of the company’s shareholders would choose the option he will offer them of “rolling” their stakes and continue to be investors in a private company, rather than cash out.

Musk also said that Saudi Arabia’s PIF, which became a Tesla shareholder earlier this year with a stake of just under 5percent, could help him fund the cash portion of the deal, though sources close to the secretive sovereign wealth fund have played down that prospect.

There is no precedent for major institutional shareholders and thousands of mom-and-pop investors rolling their stakes in a transaction of this size, and legal experts have warned that carrying this out would require navigating a regulatory minefield.

If the deal was structured like a leveraged buyout, advisers to Tesla could earn $90million to $120million in fees, while advisers to Musk’s investor group would earn $30million to $50million, and debt financing fees could reach $500million, according to estimates from financial advisory firm Freeman & Co.

However, if the Tesla deal is done with equity partners and little debt, as Musk envisions, the fees would be substantially lower, according to Freeman, making it more of a trophy rather than a lucrative assignment for bankers.