Apparently, Mark Zuckerberg’s recent makeover and ode to “masculine energy” haven’t been enough to change his image — at least, not in President Donald Trump’s eyes.

The Meta CEO tried and, so far, failed to get Trump’s Federal Trade Commission to back off an aggressive antitrust case that could cost the company billions, or even force a breakup. Google, meanwhile, is in court in Washington, too, facing off with the Justice Department in the remedy stage of an antitrust case the government won last year — and it just lost a separate trial over its advertising tools. The penalty in both matters could prove expensive at best, and existential at worst. Despite the industry’s efforts, it seems Big Tech hasn’t managed to charm, or spend, its way out of trouble with Trump’s regulators.

Silicon Valley’s finest have been busy trying to win over Washington in recent months. You couldn’t miss the bevy of billionaires standing on the stage under the Capitol Rotunda on Inauguration Day, clapping proudly as the man of the hour promised to plant the U.S. flag on Mars: Zuckerberg, Google’s Sundar Pichai, Amazon’s Jeff Bezos (who owns The Post) and, of course, Tesla and SpaceX’s Elon Musk. Apple’s Tim Cook and TikTok’s Shou Zi Chew showed up for the festivities as well.

The contrast to eight years prior was as conspicuous as the gold chain lately hanging around the newly bro-ified Zuckerberg’s neck: Back in 2017, Pichai and Google co-founder Sergey Brin joined employees who walked out to protest draconian immigration policies.

Today, as the United States ships people off to a Salvadoran prison, due process be damned, they’re quiet. During the first Trump administration, Facebook scrambled to cleanse its platform of disinformation as well as hate — eventually, after the 2020 vote, booting Trump himself for two years over his praise of Jan. 6 rioters. Today, Meta has decided to throw up its hands.

Not long before Trump’s return to power, Zuckerberg declared an end to fact-checking, as well as a retreat from policing other sorts of nasty speech. “Too much censorship,” he intoned, also mentioning “bias” and “free expression” — watchwords among conservatives who’ve spent the past decade excoriating Zuckerberg and his Silicon Valley compatriots for going woke. That wheedling is nothing to the way Zuckerberg described Trump during an interview over the summer, soon after his attempted assassination: “badass.” Meta even paid $25 million to settle a lawsuit the president lodged over its closing of his accounts.

Regardless, last week Zuckerberg took to the witness stand for hours in an antitrust case that was filed during the waning weeks of the first Trump administration; dismissed by a federal judge; then refiled under President Joe Biden’s FTC. The Wall Street Journal reports that Zuckerberg recently called current agency head Andrew Ferguson offering to pay $450 million to settle. That’s a far and feeble cry from the $18 billion enforcers were asking for, but those in the know said the CEO sounded confident Trump would back him up. Evidently, he didn’t.

In the very same courthouse, Google confronts its own threat. The Justice Department has already convinced a judge that the search behemoth is operating an illegal monopoly. That ruling came down last summer. Now, the two parties will spend three weeks haggling over remedies. The government could have presented a cushy proposal limiting the way Google does business. Instead, it’s seeking to change what the company’s business even is: trying to force the firm to sell off its Chrome browser. Whether enforcers carry on antitrust cases against Amazon and Apple with as much vigor as they’ve displayed against Meta and Google remains to be seen.

So what lesson should Big Tech take away? Will paying to play always prove futile?

Well, not exactly. Washington has treated crypto, a tech sector that went all in for Trump in 2024, as a golden child these past few months.

The administration is going easier on that industry after bigwigs from the venture capital world tossed millions of dollars into the president’s campaign coffers. The Justice Department is disbanding its national crypto enforcement team; the Securities and Exchange Commission has been dropping cases against the industry at an impressive clip. Artificial intelligence has been similarly spoiled.

Antitrust has bipartisan support. The president and his allies could say they simply believe in going after colossi such as Meta and Google while leaving fledgling industries alone.

But no one who purports to care about consumers should ignore the harms that could be caused by any business sector, whether it’s still growing or fully formed. But Trump’s gripes with Big Tech have always been about its treatment of him, not about a principled commitment to a robust interpretation of the Sherman Antitrust Act. In fact, the president has a history of wielding antitrust as a political cudgel — ordering aides to sue to block an AT&T-Time Warner merger about eight years ago out of apparent personal animus toward CNN.

Big Tech came of age rooting for Democrats … and then against Trump. Little Tech — start-ups and upstarts in crypto, AI and beyond — are rising to prominence only now, and they know exactly where to put their money and their mouths. A simple explanation for Meta’s and Google’s continued courtroom woes could be the obvious: The president likes having his ring kissed, but he also likes revenge. That doesn’t necessary mean there’s no price that would convince him to give up his grudge. It just means, maybe, we haven’t found out what it is.

Molly Roberts writes about technology and society for The Washington Post’s Opinions section.