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Tim O'Brien on 35 years of covering Trump
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Tim O'Brien on 35 years of covering Trump

"His id and animal impulses weren’t fully unleashed in the way they are now."

Aaron Rupar's avatar
Aaron Rupar
May 13, 2024
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Tim O'Brien on 35 years of covering Trump
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Trump at Atlantic City’s Trump Taj Mahal casino in March 1990, around the time O’Brien started covering him. (Getty)

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Ten years before Donald Trump came down that golden escalator to change the course of American history, Tim O’Brien had already exposed him as a fraud.

O’Brien, now the senior executive editor of Bloomberg Opinion, is the author of “TrumpNation: The Art of Being the Donald.” In that 2005 book, O’Brien wrote that Trump was not the billionaire he cracked himself up to be — not even close, as O’Brien estimated his net worth to be no more than $250 million.

Trump’s response to O’Brien’s reporting was extremely on brand. He brought a $5 billion defamation lawsuit, and when it was finally tossed three years later, he offered a now-familiar complaint: “The libel laws are very bad.”

O’Brien spent nearly 15 years reporting on Trump’s businesses ahead of “TrumpNation” and continued to follow him closely as he took over the GOP, became president, lost the 2020 election, attempted a coup, got hit with four criminal indictments, and now attempts to return to the White House. Public Notice contributor Thor Benson recently connected with O’Brien to discuss his 35 years covering Trump and how he’s changed from a television star known as “The Donald” to perhaps the most dangerous right-wing demagogue in American history.

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“His embrace of birtherism and anti-Obama racism more than a decade ago foreshadowed the bile he'd transport into the White House later,” O’Brien told us. “But I never imagined he'd become the centerpiece of an authoritarian movement that wound up rocking the Republican Party and US politics to their cores.” 

O’Brien also argued that the 2024 version of Trump is more dangerous than any previous one.

Read O’Brien’s column here.

“He’s full of vengeance and resentment and a raw and violent desire to get even, because he was impeached twice,” he said. “He’s got a whole series of civil and criminal litigations he’s contending with. He’s had massive fines levied against him through the courts. He lost to Joe Biden. All of those things have created this stew of resentment and a search for retribution. That’s certainly more dangerous now than it’s ever been before.”

A full transcript of our conversation with O’Brien, lightly edited for length and clarity, follows.

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Trump's political views have obviously changed a lot over the years. When you were spending a lot of time around him during the 1990s and early 2000s, did you get any sense he was passionate about politics or for what his views were? Were there any indications he might run for president someday, and would it have surprised you back then to learn that Trump would ultimately become a champion for the far right?

Tim O’Brien

He mulled running for president, or actively entered the race, several times since the mid-1980s, so the 2016 campaign didn’t come out of nowhere. But his motivation was never policymaking or public service. It was raw self-aggrandizement and free publicity that initially attracted him to presidential campaigning.

Trump wasn't serious about it most of the time, including, I think, early on in the 2016 cycle. But then, to the surprise of many — and himself — he got real traction. And here we are now.

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