We know who’s not laughing over the apparent collapse of Elon Musk’s tender offer to take Twitter private. After the deal fell apart late Friday, shares in Twitter began falling and have now sunk 5% below last week’s close in pre-market trading. That’s a billion-dollar-plus loss for Twitter’s shareholders, leaving the board to face the ire of its investors:

Twitter shares sank in premarket trade Monday after Elon Musk said he is trying to terminate his $44 billion takeover of the company.

Shares of the social media platform were down 5% in U.S. premarkets, implying a loss of nearly $1.4 billion in market value from Friday’s closing price. Tesla, where Musk is CEO, was slightly higher.

On Friday, Musk’s attorney notified Twitter’s board that he wants to cancel the deal. The billionaire has taken issue with the number of bots and fake accounts on Twitter and says the company isn’t being truthful about how much activity on the service is authentic.

Twitter, on the other hand, says it has given Musk the information he needs to assess its claim that spam accounts make up only 5% of monetizable daily active users, including its so-called firehose, an unfiltered, real-time stream of daily tweets.

If the shareholders are the losers, does that make Musk the winner? Well, no, because Musk already owns 9% of Twitter’s total shares. The drop in price hurts Musk as much as it does any other shareholder, and more than many of them. CNBC estimates that Twitter has lost $1.4 billion in market capitalization in the fall just this morning, and 9% of that is Musk’s — which comes up to well over $100 million.

However, Musk doesn’t appear to be mourning the market reaction or too worried about Twitter’s threat to force Musk to execute the sale in court. In fact, Musk seemed positively gleeful this morning:

Chuckmate

— Elon Musk (@elonmusk) July 11, 2022

pic.twitter.com/JcLMee61wj

— Elon Musk (@elonmusk) July 11, 2022

Musk wants to make it look like he’s laughing all the way to court, if not the bank, despite the loss in value of his shares and a potential $1B penalty. CNN notes that and the potential reason for Musk’s professed optimism in achieving “chuckmate”:

Musk disclosed late Friday he was pulling out of his agreement to buy Twitter, citing the lack of information about the number of Twitter users made up of bots. His lawyer said that placed Twitter “in material breach of multiple provisions” of the original agreement.

Twitter responded by saying it would “pursue legal action to enforce the merger agreement.”

In other words, Musk wants to make this look like a classic briar-patch strategy. And who knows? It might work, especially if Twitter has been knowingly misrepresenting the percentage of bots in its customer base to advertisers. If that’s the case, then the company would likely start negotiating a lower buyout price to settle matters with Musk and to mollify shareholders.

That, however, is a rather large If, and it’s a rather costly one under the circumstances. Musk might still be required to execute the $44 billion purchase in court, if the due-diligence issues were waived in the sales agreement as reported. At the very least, Musk is risking both the $1 billion penalty and the loss of value in his own Twitter shares for getting his “chuckmate” … over a dispute about bots that matters only as a curiosity for most people on the platform.

Wouldn’t it have been a lot easier to just buy Twitter and really own the libs, as opposed to shelling out a billion dollars to end up owning nothing at all except a chance to embarrass them momentarily? And what happens if Twitter’s been reasonably accurate in its bot assessment? Musk will get stuck with the sales agreement. Even if Musk can force Twitter to open the books and prove them wrong, he’s still at risk for the billion-dollar penalty, since that is an issue that Musk should have considered before making his tender offer. And proving Twitter wrong on bots is akin to nailing Al Capone not on tax evasion but on a zoning regulation infraction.

Musk’s laughing, and he’s a pretty smart guy, so perhaps he has something else up his sleeve. But so far, a chance to get sued and go through discovery doesn’t sound like all that much fun, useful, or profitable in any real sense.