The Art of the (New) Deal: How America’s Top CEOs Navigate Trump 2.0
Navigating policy shifts, public pressure, and unpredictable power plays in Trump’s America
If you’re a corporate chieftain, at the outset of the Trump administration, you would probably have acquired, among the many similarly titled books out there, something like “Leadership: In Turbulent Times” by Doris Kearns Goodwin that teaches you how to weather the storm.
Instead, they ended up shopping for books under the genres of macroeconomics, free trade, climate change, rare-earth minerals deal-making, communist diplomacy, financial system overhaul with cryptocurrency, and — how can we forget — the all-time favourite, “The Art of the Deal.”
Little could anyone foresee that the turbulence unleashed in the first quarter did not impact only one, but several systems that have been in place since World War II and have worked wonders for a large segment of America and her allies.
So how would you deal with Trump if you were a corporate leader?
Would you be pragmatic? Trump does come across as quite pragmatic; sometimes he is too vocal for pragmatism’s sake.
Can you argue? Maybe… negotiate… He will use the principles of “The Art of the Deal,” and whichever way the negotiation goes, he will claim that he got a better deal.
Let’s take a look at how some of the most prominent business figures — Elon Musk, Tim Cook, Mark Zuckerberg, Jensen Huang, Satya Nadella, Jamie Dimon, Michael Bloomberg, and Andy Jassy — have interacted with Trump, and the ways they’ve had to adapt or work around their own boundaries to stay in the game.
Elon Musk
Let’s start with Musk. This is someone who reaped the advantages of having government handouts in California for his EVs. In fact, one could almost say that it’s these handouts and benefits that have taken Tesla to being the number one EV company in the world.
It was therefore opportunistic that he turned around and began to support Trump the moment he saw the tides turning.
The relationship between Musk and Trump could best be described as confusing. Trump needed Musk to clean the swamp (DOGE) while keeping his hands clean. Musk needed favors from the government, which until now have been coming in bits and pieces.
Having said that, both leaders swear in public about their great relationship, something which close associates often giggle at.
Musk, for his credit, appealed to the side of Trump that wanted to clean up the government. This is probably what he may be most remembered for in Trump’s second term, unless, of course, he does send someone to Mars in the next three years!
Tim Cook
Talk about Tim Cook and instead of Apple, it’s China that comes to my mind. After all, this is the man who is credited for relocated Apple’s entire supply chain to China, thereby making it affordable to a majority of the global population of iPhone users.
Tim has had to deal with a ton of issues with Trump which include differences on issues like immigration and climate change. He has however been able to navigate this terrain carefully while maintaining a working relationship with the president, often negotiating directly to mitigate the impact of tariffs and other policies on Apple’s global supply chain.
However, Trump’s recent demands for Apple to halt manufacturing expansion in India and increase U.S. production illustrate this constant push-and-pull, especially with a business whose main motto is to increase shareholder value. Despite Cook’s on-the-ground commitments to build sizeable infrastructure in the US, Trump is not placated.
Cook will have to skillfully navigate this relationship with Trump. Like him, many will have to concede ground to Trump. However, a large part of Apple’s user base is also in China, and being torn between nationalism and capitalism was not what he had in mind.
Mark Zuckerberg
To be fair, Mark has had a very rough ride as CEO and founder of Facebook. From not doing enough about cyberbullying on Facebook to a botched metaverse spending plan running up to $ 10 Billion, many people still consider him to be the face of social media.
It’s no surprise that Facebook seemed to be pioneering content moderation after all the heat they had to take.
Everyone was surprised when Mark Zuckerberg took a U-turn and visited Mar-a-Lago earlier this year to kiss the proverbial ring. What followed soon after were rollbacks in content moderation, the ending of third-party fact-checking, and, to please Trump the most, scaling back diversity initiatives.
For Mark, it was a question of swallowing a bitter pill. He just had too much to lose and probably had to cave in and completely change course to survive.
Jensen Huang
Caught between the devil and the deep blue sea, Jensen is. He knows that China is one of NVIDIA’s biggest markets. He needs to keep selling there but must ensure that the latest GPU chips are not sold to China due to U.S. export controls.
This places additional pressure on his company to design specific chips for China that do not cross the limits set by the U.S. government — limits that are increasingly difficult to define in today’s rapidly evolving tech landscape.
Jensen Huang was born in Taiwan, which adds another layer of complexity given the geopolitical tensions. Moreover, the global semiconductor supply chain has critical stopovers in foreign countries; he cannot possibly shut the world out, at least not just yet.
Just like Tim Cook, it takes a shrewd businessman to navigate this terrain cautiously while avoiding the pitfalls of the US-China trade war. However, unlike Apple, NVIDIA is a fabless company and does not manufacture its own chips. Its GPUs are primarily fabricated at TSMC in Taiwan. The U.S. government restricts the sale of NVIDIA’s most advanced chips to China.
Huang’s engagement, therefore, is driven by his need to protect his company’s interests in a perpetually turbulent policy environment involving China.
Jamie Dimon
The CEO of JPMorgan Chase is a banker whom a lot of people tune into for insight and market commentary. With JPMorgan’s footprint almost all over the globe and investments in markets both within and outside the US, merchant banks like them are carefully watched.
JPMorgan Chase CEO Jamie Dimon has maintained a complex relationship with Trump, providing private counsel on economic policy while publicly criticizing certain administration actions and ruling out a formal role in government.
As recently as May 2025, Dimon warned that Trump’s scaled-back tariffs still pose significant risks, including potential stock market sell-offs and credit crunches, and could trigger a recession.
This blowing hot and cold approach seems to be working so far. Trump seems to be okay with financiers just weighing in, while waiting and watching to see what he does next.
On the whole, navigating Trump 2.0 has become a masterclass in adaptive leadership for America’s top CEOs. Many of the twists and turns defy conventional wisdom and known logic.
Whether it’s Elon Musk’s unpredictable alliances, Tim Cook’s delicate supply chain diplomacy, Mark Zuckerberg’s strategic pivots, Jensen Huang’s global balancing act, or Jamie Dimon’s candid counsel, each leader has had to recalibrate their approach in response to Trump’s transactional, high-pressure style.
The playbook for success is no longer just about operational excellence or corporate vision; rather, it’s about mastering the art of negotiation, managing public perception, and knowing when to stand firm or bend.
