The thesis for investors in Trump Media and Technology Group (TMTG) is that if Trump wins in November, the media company that bears his name will become extremely valuable. However, if Trump loses that logic goes out the window, according to Mattew Tuttle, CEO of Tuttle Capital Management. 

If “Trump loses I think it eventually goes to zero,” Tuttle told Fortune.    

This could be a financial problem for the former President. Trump’s shares in Trump Media form a major portion of his personal wealth. They have helped boost the Republican nominee’s net worth to some of the highest levels on record. Trump’s current net worth is somewhere between $7.5 billion and $10 billion, according to estimates from the Wall Street Journal.

Trump currently holds a roughly 60% stake in the company, valued at around $4.3 billion based on the current share price of $38. Until now, Trump has not sold any of his stock in the company. However, Tuttle believes that would change were Trump to see defeat in the election. 

“I don’t think he will be involved in it,” said Tuttle, who personally owns put options against TMTG. “He will need to sell his shares to pay legal expenses.”  

Trump was previously TMTG’s chair, but has no current role at the company. TMTG did not respond to a request for comment.

The former president is standing trial in several criminal cases across the country. In Georgia, Trump faces charges related to his alleged efforts to convince state election officials to add votes in his favor so that he would have more than President Joe Biden. Trump was also indicted in two federal cases that alleged he took classified documents to his Mar-a-Lago golf resort in Palm Beach and led a conspiracy to overturn the 2020 election. In New York, Trump has been convicted of 34 felony counts of falsifying business records. He is currently appealing the case. 

“If he loses, my sense is that they will go after him on all these cases and he will be eventually forced to sell,” Tuttle said. “When and how depends on his cash flow—it won’t be easy. And if people see him coming it will be a bloodbath.”

Despite the huge paper fortune Trump’s TMTG shares represent, selling them will prove to be a difficult task. Trump currently owns about 114.5 million shares, a stake so large that selling it on the open market would almost certainly lead to a fire sale. In all likelihood Trump would manage to sell only a portion of his shares before the rest became effectively worthless with the stock bottoming out. Tuttle believes Trump would need to find an institutional buyer to purchase the entire block of shares at a “massive discount.” 

If Trump does win the election, which is certainly a possibility given the race is a toss-up, investors in TMTG would likely cash out all at once. “I would expect the stock to immediately drop as everyone who bought before the election takes profits,” Tuttle said. 

After the initial drop as investors harvest their returns, TMTG could still be appealing long-term buy in a second Trump administration. “Trump in office I think they have a chance to make something out of this company and as he will continue to be in the news,” Tuttle wrote. 

In that case, Trump would likely hold his TMTG stock. Ordinarily if a sitting president held an ownership stake in a media company, that would present conflict of interests. But Trump is an exception, according to Tuttle.  For “anyone but Trump yes, but Trump is a walking conflict of interest so I assume it will work,” he said.