Shares of Trump Media & Technology Group (NASDAQ: DJT), the parent company of conservative social media platform Truth Social, have plunged to new lows as the lockup period for major shareholders, including former President Donald Trump, approaches its expiration. The expiration will allow Trump and other significant shareholders to sell their shares for the first time since the company's public debut in March through a special purpose acquisition company (SPAC).

Despite the declining share price, Trump, who holds approximately 57% of the company's outstanding shares, equivalent to 114.75 million shares, worth an estimated $1.7 billion as of the latest trading session, has publicly stated that he has "absolutely no intention" of selling his stake. Trump's commitment to holding onto his shares initially boosted the stock, yet it has since continued on a downward trend. His control over the company is further solidified by a special voting class of shares, ensuring he maintains majority voting power even if his equity stake decreases.

The market reacted negatively to the impending end of the lockup period, with Trump Media shares falling over 3% to close at $15.64 on Wednesday, marking the second consecutive day of record lows. This slide represents a significant drop from its March highs, where shares had soared to $79.38. The company's valuation has plummeted by over 80% from those peaks.

Adding to the turmoil, a Delaware court recently ruled that Trump Media had breached a contract with early investor Patrick Orlando, awarding Orlando around 800,000 additional shares, further pressuring the stock. The company had attempted to block ARC Global, another early investor, from selling its shares post-lockup but was denied an injunction by a Florida court.

Investor sentiment remains cautious, with concerns that significant share sell-offs by early backers could further depress the stock price. These apprehensions are underscored by Trump Media's financial struggles, having reportedly lost $344 million on under $2 million in revenue for the first half of the year. The company's revenue stream heavily relies on ad sales, and Truth Social's user base is minuscule compared to larger social media platforms.

Trump Media's market capitalization currently stands at roughly $3 billion, sustained partly by retail investors who view their investment as a show of support for Trump. This support has seen fluctuating fortunes tied closely to Trump's ongoing presidential campaign and legal issues.

As the lockup period's end looms, all eyes are on whether Trump and other shareholders will offload their stakes, an event that could significantly shape the company's financial and market trajectory moving forward.