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Trump’s Media Company Investigated Over SPAC Deal

That month, a small investment bank, Kingswood Capital Markets, which has frequently teamed up with ARC, made a presentation to Benessere’s board members. Marked “strictly private and confidential,” the presentation, reviewed by The Times, listed about a half-dozen possible acquisition targets. One was Trump Media. Kingswood, now called EF Hutton, estimated that Trump Media was worth $1.5 billion and that within a few years it could generate $2.3 billion in annual revenue.

Sergio Camarero, a managing partner at ARC, told Benessere officials that Trump Media was their preferred target. Some Benessere officials, however, balked because they didn’t want to have anything to do with Mr. Trump, two people familiar with the discussions said.

Mr. Camarero did not respond to requests for comment.

ARC quickly turned to Digital World, its other SPAC, as a potential vehicle to merge with the Trump company. ARC had recently installed Mr. Orlando as Digital World’s chief executive, after its previous C.E.O. failed to raise enough money to get it off the ground, a person with direct knowledge of the situation said.

The videoconference call involving ARC, Mr. Orlando, Mr. Veloso and members of the Trump team took place in early April. At the time, Digital World had not yet filed with the S.E.C. to sell its shares to the public. It did so seven weeks later, on May 26.

“We have not selected any specific business combination target and we have not, nor has anyone on our behalf, initiated any substantive discussions, directly or indirectly, with any business combination target,” Digital World said in its initial filing.

The disclosure was important. Because regulators allow blank-check companies to sell their shares to the public with minimal financial disclosures, the companies are not allowed to have merger partners in mind before their I.P.O.s. The thinking is that they otherwise would serve as a backdoor channel for companies to go public while escaping rigorous public scrutiny.

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