Trump Deal Delivers $420 Million Windfall for Wandering Dealmaker

Former US President Donald Trump’s merger with a new social media venture has yielded a potential $420 million profit for a former finance executive who has been trying to reinvent himself as a serial dealmaker for a decade .

Benesere Capital CEO Patrick Orlando’s stake in Digital World Acquisition Corp., the Miami-based blank-check acquisition firm he is leading, stood at $423 million after Trump Media & Technology Group announced a merger deal on Thursday. According to a regulatory filing and Reuters calculations.

Orlando just invested $3 million in Digital World, and is set to reap the windfall because the deal deserves additional compensation in shares as the firm’s sponsor, the filing shows. Shares of Digital World traded up 357% on Wednesday after the deal was announced, bringing the firm’s market value to close to $1.5 billion.

To be sure, these benefits are on paper. The terms of the SPAC do not allow Orlando to cash out until six months after the merger is complete.

Yet it marked a notable reversal of fortune for the former Deutsche Bank AG derivatives banker, who worked for Peru’s biofuels industry and a US sugar trading company before trying his hand at special purpose acquisition companies (SPACs).

He launched Benesare in 2012 to advise other companies on their deals, but it wasn’t until last year that he launched four SPACs with the help of Shanghai-based investment bank ARC Capital.

He struggled to gain traction. One of their SPACs, which was based in Wuhan, China, last month failed to complete a merger with Giga Energy Inc., which would have valued the transportation solutions provider $7.3 billion because it could not deliver the cash needed, the regulator said. According to the filing.

Orlando did not respond to requests for comment.

Trump Media said it would receive $293 million in cash in Digital World’s trust if any shareholders of the acquisition firm chose not to redeem their shares.

The company said it planned a trial version of its social media app next month and a full roll-out in the first quarter of 2022.

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