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Indebta > News > Flatter Trump or fight him? Smart billionaires do both
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Flatter Trump or fight him? Smart billionaires do both

News Room
Last updated: 2026/01/22 at 8:12 PM
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Your guide to what Trump’s second term means for Washington, business and the world

One of the remarkable things about the Donald Trump administration is how keen corporate executives are to avoid the US president’s wrath. Some have U-turned on past unsupportive remarks. Many have paid tribute through donations, proclamations and Trump-approved philanthropic acts. But what, really, is the cost of getting in the big man’s bad books?

Jamie Dimon may supply the answer. The JPMorgan boss found himself landed with a $5bn lawsuit on Thursday that accuses him — personally — and his employer of improperly denying bank accounts to the Trump family. JPMorgan’s response was surprisingly robust. The president is free to sue and the bank is free to defend itself: “That’s what courts are for.”

Dimon is an odd target, because he has mostly been good at managing up without sucking up. He branded Trump’s early tariff plans “too aggressive”, and a recent plan to cap credit card rates “an economic disaster”. But he has also picked his battles, praising Trump’s common sense and US-first policies. Sometimes he can be mealy mouthed, describing attacks on central bank independence as “probably not a great idea”.

Indeed, JPMorgan and its peers have reasons to be grateful for Trump. They have benefited from friendlier regulation, a buoyant stock market and a resurgence in corporate dealmaking. All would have been less likely had Trump and his Republican Party lost the 2024 election. The hated Consumer Financial Protection Bureau, which had slapped banks with $25bn in fines and consumer relief, has been gutted over the past year.

Dimon is also, though, in a better position than most to politely push back. Lenders like JPMorgan and Bank of America — whose chief executive Brian Moynihan has also felt the sharp edge of Trump’s tongue — are so woven into the economy that what hurts them could hurt the White House too. And with red tape already in retreat, there’s not much more they need in the way of special favours.

For some supplicants in other industries, good relations with the commander-in-chief are more than a nice-to-have. Nvidia chief Jensen Huang, who has gushed over Trump’s “genius”, depends on government permission to sell his company’s microchips to China. Chevron boss Mike Wirth was one of the first CEOs to refer to the “Gulf of America”, as decreed by the White House, but since Chevron requires special export licences to ship oil out of Venezuela, his investors are probably glad he did.

Then there’s Elon Musk, both example and counterexample of the benefits of getting along. The Tesla boss has variously flattered Trump, worked for him, defied him and insulted him, and still come out wealthier. His rocket maker SpaceX may float this year with a valuation of $1.5tn, Bloomberg has reported, quadruple what it was when Trump started his second term.

Dimon has found the balance in a less haphazard, more strategic way. While vowing to fight Trump’s legal challenge, JPMorgan on Thursday praised the president for combating the political “weaponisation” of the banking system that forced it to cut him off in the first place. Smart billionaires know the way to navigate this administration is not to fawn or to fight — it’s to do just enough of both.

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News Room January 22, 2026 January 22, 2026
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