Elon Musk’s takeover of Twitter is already off to a rocky start, and his decision to bring in Tesla employees could come back to haunt him.

The multitasking CEO faces yet another trial before the very Delaware judge who forced him to honor his contract with Twitter’s board to purchase the social media company. This time, however, it’s about something much more personal: his own pay.

Starting Nov. 14, Elon Musk as well as present and former directors must stand before the state’s Court of Chancery’s Kathaleen McCormick to defend a mammoth compensation package handed out in 2018 that entitled him to up to $55.8 billion in stock options.

Unlike the Twitter case, it is expected this will not likely result in a prior settlement.

Plaintiff Richard Tornetta is arguing in a 96-page legal brief that the board failed to perform its fiduciary duty to minority investors by green-lighting “the largest compensation grant in human history”—even though the grant was put to a shareholder vote and approved.

At its heart is the issue whether Elon Musk can be considered a controlling shareholder on both sides of the transaction—as chairman of the board owning a 22% stake at the time, as well as the beneficiary of the package. If he were, the deal would be considered a conflicted transaction subject to different governance rules.

Close ties

“Musk’s problem is that he has close ties to a lot of directors,” said Tulane University law professor Ann Lipton. “If you are deemed to be a controller, conflicted transactions cannot be cleansed with a shareholder vote alone. You also need a disinterested and independent board committee, and a more formalized process, which wasn’t followed here.”

Toretta argues Musk was furthermore not truly incentivized, since the milestone payments set out also happened to align with goals already baked into the company’s projected business plan.

While a ruling rests on decisions that took place four years ago, recent events at Twitter could play a role. Musk has commandeered a staff of reportedly 50 Tesla employees including senior managers like Ashok Elluswamy as his own personal aides-de-camp in restructuring Twitter’s operations.