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Truth Social's civil war

A legal battle royale involving Trump Media's co-founders and ex-financier could threaten one of the former president's financial lifelines.

Drew Harwell

Mar 21, 2024 — 2 min read

Donald Trump and Patrick Orlando in happier times. (Will Wilkerson)

Full story: Trump Media, launched after an insurrection, faces rebellion of its own

This was supposed to be a happy time for Trump Media and Technology Group, the owner of former president Donald Trump's social network Truth Social: After years of delays, it finally had a date for shareholders to approve its giant merger deal.

Instead, the company has been consumed by an all-out legal war, which threatens to derail the deal entirely and zap a Trump lifeline:

After Trump was booted from Twitter following the Jan. 6, 2021, insurrection, three men played pivotal roles in building and promoting Trump Media as an online challenger against the “cancel culture” of Big Tech ... But all three are now leading a rebellion of their own, confronting and potentially imperiling a trophy of Trump’s post-presidential ambitions.

... In a fourth lawsuit, filed in Florida, Trump Media and Digital World returned fire at Arc and Orlando, saying the Miami financier had attempted a “blatant shakedown extortion effort” against the companies to maximize his personal stake.

An amended complaint Sunday, featuring the names of nine attorneys representing Trump Media and Digital World, alleged that Orlando and Arc’s “self-dealing, irrational and disturbing behavior” had “imposed massive costs” and caused “extensive reputational harm.”

They want to “extort more compensation in the merger by threatening to destroy it entirely — an existential threat to [Digital World] itself,” the complaint said.

... Though Orlando was once a prominent Trump ally, even writing him a birthday letter in 2021 telling Trump he was “unaware of the extent of your brilliance,” the legal claims suggest the dispute has become deeply bitter and personal.

In the Florida case, a process server handed Orlando the summons papers one afternoon outside a private elementary school in the Miami neighborhood of Coconut Grove, a court filing shows. In a Delaware court hearing earlier this month, one of his attorneys said Orlando had been served when he was “getting off the bus from a field trip with his daughter, in front of her fifth grade class and their parents,” leaving the attorney “so taken aback," according to a hearing transcript.