Facebook founder Mark Zuckerberg was straight out of central casting when he became a household name.

His allegiance to his pigeon gray T-shirt and dorm-room dork aesthetic made him a hero to many and synonymous with the Silicon Valley pledge to “move fast and break things.”

Catty fashion writers obsessed over his $300-a-pop custom-ordered Brunello Cucinelli T-shirts styled to look like they were bought at the Gap outlet store. His hair also piqued their interest, with one writer at W magazine describing it as doing the “heavy lifting” when it came to his physical appearance.

“Cut back into his sweaty pate in a near-tonsure, it made him look like a Capuchin monk [had] come down from the monastery for his lashings,” is how he described it.

But over the past few years, Zuckerberg has transitioned from being the blandest bro on the block to evolving stylistically and politically in a bid to lengthen his multibillion-dollar company’s longevity.

In 2009, the once-hoodie-obsessed wunderkind wore a tie to work every day. At the end of the year, he wrote why.

“After the start of the recession in 2008, I wanted to signal to everyone at Facebook that this was a serious year for us,” Zuckerberg wrote. “Great companies thrive by investing more heavily while everyone else is cutting back during a recession. But great companies also make sure they’re financially strong and sustainable. My tie was the symbol of how serious and important a year this was, and I wore it every day to show this.”

Since then, Zuckerberg has done even more to change his image, ditching the tie for sharp suits and designer duds.

“The history of Silicon Valley has always been about a carefully constructed image and narrative used to reinforce its myths,” said Venky Ganesan, a partner at the venture capital firm Menlo Ventures.

The playbook is changing

Zuckerberg has gone from holding court on bean bag chairs to surfing and learning mixed martial arts. One of his MMA sparring sessions landed him in the hospital last year with a torn ACL.

Jaws dropped again this year when Zuckerberg posted an Instagram video of himself talking about Meta’s AI assistant.

He had grown out his hair, showed off his muscles, and sported a chain necklace.

“Went from steal my data, to steal my wife and kids,” one commenter posted on social media.

Someone else used a still photo from the video to give Zuckerberg an even bigger glow-up by adding facial hair. The doctored image went viral and people started swooning over the new look.

On July 4, the 40-year-old shared a video of himself wakeboarding while wearing a tuxedo and sipping on a tall boy. He did it to the backdrop of Bruce Springsteen’s “Born in the U.S.A.”

“Now that’s content,” gaming influencer @StoneMountain54 wrote.

Zuckerberg replied, “Just doing my part.”

Keeping it cool for millennials

To those schooled in Zuck-ology, the move was yet another example of the billionaire’s attempt to remake his image and stay relevant.

“Mark Zuckerberg’s image shift reflects Meta’s business evolution,” Joseph Rosenfeld, an image consultant who works with executives in New York and California, told the Washington Examiner. “His style has shifted to align with the company’s focus on interactive, consumer-driven products. He moved from a ‘stealth wealth’ look to one featuring brand names, many of which advertise on Meta’s platforms. This strategic move helps him connect more directly with the platforms’ users and advertisers, ensuring he remains current and relevant in a competitive tech space.”

Between December 2019 and January 2020, Zuckerberg exchanged a series of emails with his colleagues and then-board member Peter Thiel on how Facebook could stay attractive to millennials.

“While our company has a special role in the lives of this generation, this is likely particularly important for how I show up because I am the most well-known person of my generation,” Zuckerberg wrote in a Jan. 4, 2020, email that was disclosed as part of a lawsuit against the company.

Thiel also weighed in, saying that Meta’s popularity among the group meant that Zuckerberg has been “cast as the spokesman for the millennial generation.”

Zuckerberg, Thiel believed, is seen as “the single person who gives voice to the hopes and fears and the unique experiences of this generation, at least in the USA.”

Zuckerberg responded, writing, “It’s something I’m definitely going to think about more in terms of how I communicate.”

His fashion choices, flashy jewelry, and fondness for fighting in cages have made him go viral frequently as he continues to shed his nerdy image.

The scandal that led to a political makeover

Much like his image, Zuckerberg’s political leanings have also changed with time.

In the decade after he founded Facebook, now known as Meta, Zuckerberg made it clear that he didn’t care for politics.

Early advisers strained to hold his attention in briefings about Washington lawmakers, the Wall Street Journal reported, adding that he preferred to leave the politics to others while he focused on Facebook.

But then his and the company’s reputation took a big hit during the Cambridge Analytica scandal.

Facebook was accused of allowing 87 million of its users’ personal information to be harvested and fed to Cambridge Analytica, a firm with ties to former President Donald Trump’s political strategist Stephen Bannon. The data were used to target voters during the 2016 presidential election, which Trump won. News of the leak led to Zuckerberg being summoned to Congress to face tough questions on the company’s mishandling of data.

The uproar led to waves of people deleting their Facebook accounts in protest.

Since then, the Silicon Valley savant has upped his political game. He’s testified before Congress a handful of other times, dined at the White House with Trump, and spoken regularly to Trump’s then-senior adviser, Jared Kushner.

Zuckerberg was among the first to raise the alarm and press lawmakers to do something about the threat from Chinese tech companies as well as his rivals at Apple and TikTok.

Forging relationships with political leaders, activists, and media personalities was all part of his fight to keep Meta at the top.

Zuckerberg becomes Enemy No. 1

Zuckerberg’s interactions with Trump took a sour turn during the last election cycle. The former president has openly and repeatedly accused Zuckerberg of plotting against him in the 2020 presidential race and recently claimed the Meta chief would “spend the rest of his life in prison” if he tried to do it again. He also said he would have banned Facebook while he was president but that Zuckerberg “kept calling” him.

Following the Jan. 6, 2021, Capitol attack, Meta “indefinitely” suspended Trump’s accounts, claiming the former president used the platform “to incite violent insurrection against a democratically elected government.”

“[Trump’s] decision to use his platform to condone rather than condemn the actions of his supporters at the Capitol building has rightly disturbed people in the US and around the world,” Zuckerberg wrote in a post at the time. “We removed these statements yesterday because we judged that their effect — and likely their intent — would be to provoke further violence.”

Trump, still bitter about Facebook, praised Nigeria in 2021 after the country announced that it would block access to Twitter after a tweet by President Muhammadu Buhari seen to be inciting ethnic violence was removed.

Even though the ban was with another company, Trump still celebrated Nigeria’s response and tied Facebook to it.

“More COUNTRIES should ban Twitter and Facebook for not allowing free and open speech — all voices should be heard,” Trump said in a statement. “Perhaps I should have done it while I was President but Zuckerberg kept calling me and coming to the White House for dinner telling me how great I was.”

Trying to undo the damage one ‘Zuckerbuck’ at a time

In 2023, Meta reinstated Trump’s Facebook and Instagram accounts, but the damage had been done.

In July, Trump said in an interview that he viewed his plan to ban TikTok a little differently these days.

“Now that I’m thinking about it, I’m for TikTok because you need competition,” Trump told Bloomberg Businessweek. “If you don’t have TikTok, you have Facebook and Instagram, and that’s, you know, that’s Zuckerberg.”

Still, Zuckerberg tried to appeal to the former president.

During a recent interview, he called Trump’s reaction to the assassination attempt against him in Butler, Pennsylvania, “bada**.”

“Seeing Donald Trump get up after getting shot in the face and pump his fist in the air with the American flag is one of the most bada** things I’ve ever seen in my life,” he said. “On some level as an American, it’s, like, hard to not get kind of emotional about that spirit and that fight, and I think that that’s why a lot of people like the guy.”

Zuckerberg also made headlines when said he wasn’t planning to endorse any candidate for president this election cycle and would not donate money to enhance voting access in the United States.

Zuckerberg had come under attack from Republicans for donating more than $300 million to organizations focused on improving the voting process and promoting safe and reliable voting in states and localities during the pandemic.

“These donations will help to provide local and state officials across the country with the resources, training and infrastructure necessary to ensure that every voter who intends to cast a ballot is able to, and ultimately, to preserve integrity of our elections,” Zuckerberg and his wife Priscilla Chan said in a statement at the time.

The funds were praised by Democrats and slammed by Republicans who referred to them as “Zuckerbucks” and claimed they helped President Joe Biden win in battleground states.

“I know that some people believe this work benefited one party over the other,” Zuckerberg wrote, outlining his plan for this year’s election. “My goal is to be neutral and not play a role one way or another – or to even appear to be playing a role. So I don’t plan on making a similar contribution this cycle.”

The decision to cut the flow of funds was hailed as a victory by Republicans.

Throwing Biden under the bus

Zuckerberg also admitted in a letter to congressional Republicans that the Biden administration pressured Meta to censor certain content related to the COVID-19 pandemic. He seemed frustrated that the company caved to the administration’s demands and said Meta would be “ready to push back” should it face a similar situation in the future. The letter gave Republicans the ammunition to rip into the Biden administration and criticize it for overstepping its authority.

Nu Wexler, a former Democratic congressional staffer and former spokesperson for top tech firms in Washington, including Meta, told Politico that the letter seemed like an attempt to tamp down Republican anger over Meta’s alleged anti-conservative bias.

“Like most other large companies before a toss-up election, Meta is probably hedging its bets here,” he said.

Stephen Farnsworth, a political science professor at Mary Washington University, told the Washington Examiner he agrees.

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“His latest apologetic comments are part of trying to curry favor with Republicans in case Trump and congressional Republicans win the upcoming election,” Farnsworth said. “Angry Republicans can be very bad for business, particularly if Trump wins and tries to punish Meta next year.

“In the end, Zuckerberg wants to keep Meta in the good graces of all politicians, and as free from regulation as possible, regardless of who wins in November. And right now, Zuckerberg seems to fear Republican wrath more than Democratic wrath in the months ahead.”