Microsoft and Apple have for decades been seen as the Yin and Yang of the tech world, with Microsoft’s products portrayed as being for buttoned-corporate drones, while Apple’s were for the truth seekers and rebels — the people willing to stand up to those in power. 

Those cliches reflected the way the company’s founders and long-time CEOs were depicted as well: Steve Jobs the rebel, Bill Gates the business drone.

My, how times have changed. These days Apple CEO Tim Cook has become one of tech’s Sycophants-in-Chief to US President Donald J. Trump, while Microsoft CEO Satya Nadella, in his own quiet way, has been the only tech exec to face the president down when necessary. 

Apple whipsaws from 1984 to the Trump era

Jobs built Apple’s mystique in two ways: creating beautifully designed, groundbreaking products and launching ad campaigns that made people feel that if they used Apple products it would prove they were rebels, free thinkers, and creatives who fought the stultifying status quo and forged their own unique path in the world.

The most well-known Apple ad from that time was the “1984” Super Bowl ad introducing the Macintosh; it showed Big Brother and his brainwashed minions defeated by a beautiful young woman armed only with a sledgehammer. The message was clear: the about-to-be released Mac would free the world from corporate drones and dull, Windows PCs.

Thirteen years later, in 1997, Apple doubled down on the message with its “Think Different” ad campaign; it portrayed groundbreaking rebels who fought the status quo, including Martin Luther King and Mahatma Gandi. The message was the same as in  1984: use a Mac to prove that you’re one of the freethinking rebels who can change the world. 

Flash forward to today. Apple CEO Cook has proved that he’s anything but a rebel. To broadcast his support for Trump and all he represents, he was front and center at Trump’s inauguration last year. Since then, he’s been in meetings with Trump multiple times, and praised Trump’s “leadership and focus on innovation.” He knows that Trump loves bling, so he very publicly gave Trump a gift made in large part of 24 karat gold.

There’s more…and worse. Only hours after ICE agents murdered Alex Pretti in Minnesota by shooting him in the back 10 times while he lay defenseless on the ground, Cook attended the gala White House screening of the new Melania Trump documentary. All the guests, including Cook, were given commemorative popcorn boxes served by gloved waiters, and a framed screening ticket.

Conservative political strategist Rick Wilson framed the scene succinctly, “If you’re a CEO willing to sit in the company of this regime, your ‘shareholder value’ excuse feels pretty blood-soaked tonight.” (Cook did later release a statement calling for “deescalation,” saying he was heartbroken over Pretti’s death and had spoken to Trump about it.)

Cook has done more to support Trump than just praise him and stroke his ego. Under his leadership, Apple has actively supported ICE. Apple banned from its app store apps such as ICEBlock that allow people to track the movement of ICE troops and warn others when sweeps are underway. When the Trump administration asked that ICEBlock be removed from the store, Apple quickly complied. Apple wrote to tell ICEBlock creator Joshua Aaron that the app was removed because it contains “objectionable…defamatory, discriminatory, or mean-spirited content.”

Not exactly the actions one would expect of a company that once extolled leaders such as King and Ghandi.

Microsoft stands up to Trump

Unlike Apple under Cook, Microsoft under Nadella’s leadership has stood up to Trump. Nadella didn’t attend Trump’s inauguration, and unlike Cook, he hasn’t made any attempt to stroke Trump’s ego — no gold gifts, no ‘Melania’ film galas. 

In addition, Microsoft fired the law firm of Simpson Thacher & Bartlett when it agreed to give Trump $125 million in free legal work after Trump threatened it. Microsoft made abundantly clear that’s why it fired the firm – for a replacement, it hired Jenner & Block, which has sued the Trump administration instead of giving in to it.

Then came Trump’s demand that Microsoft fire Lisa Monaco, its recently appointed President of Global Affairs, a former Biden administration official. (Monaco was second in command of Biden’s Justice Department and oversaw the prosecutions of Trump for misusing classified documents and trying to overturn the 2020 presidential election.)

Trump implicitly threatened to kill Microsoft’s billions of dollars in federal contracts if the company refused to fire her. He wrote on Truth Social, “Corrupt and Totally Trump Deranged Lisa Monaco…has been shockingly hired as the President of Global Affairs for Microsoft, in a very senior role with access to Highly Sensitive Information. Monaco’s having that kind of access is unacceptable, and cannot be allowed to stand. She is a menace to U.S. National Security, especially given the major contracts that Microsoft has with the United States Government.” 

Nadella ignored Trump. Monaco remains on the job. Microsoft’s federal contracts haven’t been pulled.

Stagnation at Apple

There’s another way that Microsoft and Apple have changed roles since Job’s days. Under Gates’ and Steve Ballmer’s leadership in the early 2000s, the company stagnated, developing little new groundbreaking technology, choosing instead to milk Windows as its cash cow. 

Under Jobs, Apple was the innovator, developing products — including the iPhone, iPad and iPod — that changed not just the tech world, but the world itself.

These days, Microsoft is playing the innovator role, helping launch the generative AI (genAI) revolution by investing in OpenAI and incorporating ChatGPT into its products via Copilot. During Cook’s tenure, Apple hasn’t released a single groundbreaking product. 

Instead, it milks the iPhone as its cash cow while everyone waits for whatever “Apple Intelligence” turns out to be.

History’s verdict

History will remember Nadella as someone who resuscitated Microsoft from a decade of inertia and stood up to Trump. It won’t be so kind to Cook. It will recall him as a technocrat who kept Apple profitable while the company stagnated technically. It will also remember the many times he bowed down to Trump. 

And Cook won’t get anything other than cold comfort from the Melania Trump commemorative popcorn box he got in return.