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Monday, June 01, 2026

Tech billionaires are spending unprecedented sums in California races. Experts say it’s the tip of the iceberg | California | The Guardian

Tech billionaires are spending unprecedented sums in California races. Experts say it’s the tip of the iceberg

"From Google co-founder Brin spending $66m to fight a billionaire tax to Google and Meta funding a joint Super Pac, Silicon Valley is engaged in an existential fight for its political power at home

Illustration of a hand cursor placing a stack of dollar bills into a ballot box amid stacks of cash
‘They’re not looking for balance.’ Illustration: Guardian Design / Getty Images

Tech billionaires have shelled out hundreds of millions of dollars ahead of the 2 June primary election in California, in an unrivaled attempt to influence who gets to run the state that Silicon Valley calls home.

The industry has used a cover-all-bases approach, funding candidates and ballot measures big and small, contributing to what looks to be the most expensive primary season in California history. The goal, experts say, is to gain both political and regulatory leverage that will perpetuate dominance in business.

“This money is flowing in the direction of politicians that can be influential in defining the regulatory agenda for the next five years,” said Francesco Trebbi, a public policy professor at the University of California in Berkeley. “Reinforcing the cycle of economic power produces political power, and political power further establishes economic power. So, this cycle is ongoing.”

Combing through campaign finance filings with California’s secretary of state, the Guardian found:

  • Google co-founder Sergey Brin has spent $66m since January, more than any other donor, to fight a billionaire tax that’s up for a vote on the November ballot.

  • Democratic gubernatorial candidate Matt Mahan has received more donations than any other candidate, including from top executives at Google, Amazon, Snap, LinkedIn, Reddit and Palantir.

  • Crypto mogul Chris Larsen has funded three Super Pacs with $26m to sway campaigns across California, including giving $1m to back a primary candidate for state insurance commissioner.

  • Google and Meta have collectively funded a Super Pac with $10m to back assembly and senate candidates in local district races across the state.

  • Silicon Valley money is flowing toward city primaries as well as state-level ones, with tech-backed Pacs sponsoring voter guides suggesting how to vote on local tax measures.

For Silicon Valley, pouring money into politics at this moment is existential as it races to develop artificial intelligence. With favorable candidates in office, tech companies say they will be able to grow at a breakneck rate while avoiding stifling regulations.

The vast amount of spending that’s been disclosed in public records likely isn’t even the half of it, Trebbi said. People looking to sway election outcomes often fund dark money entities that aren’t traceable through campaign finance filings.

“These people are sophisticated political givers, so they will use both visible and invisible forms of influence,” Trebbi said. What we’re seeing now is “just the tip of the iceberg”.

Money-for-influence leaderboard

The influx of dollars has meant that voters from Oakland to Bakersfield to Orange County have been bombarded with TV ads, robotexts and mailers touting various issues and candidates sponsored by super political action committees (Pacs) funded by the tech industry.

Top spenders for these Super Pacs include billionaires Larsen and Brin. Larsen, the co-founder of crypto company Ripple Labs, is worth about $12bn and has spent millions on more than a dozen primary campaigns up and down the state, targeting races and issues at a city and county level, as well as bigger state-level races. Brin, worth about $290bn, has homed in on fighting a one-time 5% tax on the state’s billionaires up for a vote in November, the proceeds from which are intended to help cover education, food assistance and healthcare programs.

To date, Brin has donated at least $66m to a Super Pac dedicated to blocking the billionaire tax, according to campaign finance filings with the state. The former Alphabet president also spent $500,000 in San Francisco last month to battle a city measure that seeks to expand a tax on high-paid CEOs, which is up for a vote on 2 June. These donations come even as Brin moved out of California late last year to Nevada.

Larsen and Brin did not respond to requests for comment.

Along with contributing millions to Super Pacs and candidates in California, the tech world is also spending eye-popping amounts on lobbying.

An analysis by news site CalMatters found that in 2025 alone, the tech industry paid $39m to lobby the state government. That’s more than any year prior and surpasses what was spent by the oil and gas industry, which typically tops the high roller list. According to a Bloomberg analysis, the biggest tech and AI companies spent a collective $109m on federal lobbying in 2025; that their state lobbying in California is equivalent to 36% of their federal spend showcases the state’s importance to the tech industry.

Tech picks a favorite in the governor’s race

Of the 62 candidates listed on the 2 June primary ballot, one has stood out as the tech industry’s darling: Matt Mahan. The centrist Democrat and upstart mayor from San Jose, a large city in Silicon Valley, entered the race late and quickly made headlines as he racked up contributions from a who’s who of the tech industry.

Before Mahan got involved in politics in 2020, he had a career in the tech sector. He was an undergraduate at Harvard with Facebook co-founder Mark Zuckerberg, and in 2014 co-founded a startup with funding from the Salesforce CEO, Marc Benioff, tech investor Ron Conway and Napster co-founder Sean Parker.

Since Mahan’s candidacy announcement in late January, he’s received nearly $50m in contributions, according to Politico – more than any other gubernatorial candidate (with the exception of Tom Steyer’s self-funded campaign of about $200m). Mahan has received donations from prominent venture capitalists, along with former and current executives from Google, Amazon, Snap, eBay, PayPal, Stripe, LinkedIn, DoorDash, Reddit, Netflix, Palantir, Anduril, Roblox, Riot Games and more, public records show.

Google’s Brin donated the maximum limit for an individual campaign donation at $78,400 and contributed $1m to the pro-Mahan Super Pac Deliver for California, according to public records. Mahan flew to Lake Tahoe where Brin lives in March to make a personal appeal to the billionaire and his conservative influencer girlfriend, the New York Times reported. Brin’s girlfriend alleges that Mahan texted Brin afterwards to apologize for attending a No Kings rally.

Mahan’s overtures to both progressives and conservatives haven’t won him many friends among the state’s leading Democrats. Silicon Valley congressman Ro Khanna chose Steyer to endorse and state assembly members from Mahan’s district have publicly criticized him, saying he was “handpicked” by the tech industry. Similarly, Lorena Gonzalez Fletcher, president of the powerful California Labor Federation, saidMahan is the only democrat she’s not promoting because she’s “opposed to the candidate funded by Trump’s big tech billionaires”.

Mahan said he has no plans to cater to special interests and his goal is for the system to work for everyone.

“I’m not running for tech, and if you look at my record – I’ve been in public office now for six years – I think you’d be hard pressed to find – you would not find a single example of me ever doing something to benefit the industry to the detriment of the community,” Mahan said. “If anything, I’ve fought hard to get them to do their fair share.”

The influx of tech cash into Mahan’s race hasn’t bolstered it as much as early predictions forecast. His campaign has failed to gain traction with a wider audience and polls have put him at just 4% of the vote. The Brin-funded Deliver for California Super Pac shuttered last month.

Mahan did not respond to further questions about his interactions with Brin or the termination of the Super Pac.

Targeting state and local primaries

Although the tech industry has mostly focused on a sole candidate for the governor’s race, it has taken more of a scattershot approach in local campaigns. Silicon Valley money has infiltrated nearly every segment of politics – from local ballot measures to state congressional campaigns to the race for California’s new insurance commissioner.

The tech executive who appears most dedicated to local politics is Larsen, the crypto mogul. He’s funded Super Pacs aimed at different causes and candidates. The Golden State Promise Super Pac has received a total of $10m entirely from Larsen and Ripple Labs, public records show. The Pac, which is devoted to combating the billionaire tax that’s up for a vote in November, launched an attack ad against the tax earlier this month.

Another Super Pac supported by Larsen is geared toward the state’s insurance commissioner race. Earlier this month, Larsen donated more than $1m to the Pac, Californians for an Affordable Future, which is dedicated to electing Ben Allen, a democrat. It’s a heated primary race with several candidates vying for the seat, including Bernie Sanders-backed Jane Kim, also a democrat.

Larsen has spread his money across elections for California’s state legislature too, mostly through a Super Pac called Grow California. He’s donated $15m to the Pac, while crypto evangelist Tim Draper has contributed $5m, according to public records. Grow California’s stated goal is to “rebuild a state capital”.

The Super Pac has injected hundreds of thousands of dollars into roughly a dozen state assembly and senate primaries across California. For example, Mark Pulido, who’s running for assembly in Orange county, has received more than $1.5m from Grow California. Likewise, a senate candidate in Northern California’s Alameda County, Scott Sakakihara, has received more than $500,000 from the Pac.

“We have a group of people who are not acting in a pragmatic way. They’re not looking for balance. They’re completely fucking owned by one side,” Larsen told Politico, in reference to organized labor’s power in the legislature. “So we’re going to work on taking out those people who are not working for the people of California.”

Google and Meta have supported a similar Super Pac, California Leads, with $5m each and have distributed funds to several candidates in the Central Valley, as well as to many of the same contenders as Grow California. According to public records, Pulido has received nearly $750,000 from California Leads. The Super Pac’s stated mission is “supporting leaders focused on California’s future”.

John Bennett, director of the advocacy organization California Initiative for Technology and Democracy, said spending upwards of $500,000 on a local district primary is a “huge sum of money”. He’s been studying the races and said the bulk of tech spending has gone to about a dozen open seats in the state legislature.

“They’ve been hyper-focused on those open seats, not going after incumbents this time around,” Bennett said. “So, it seems like they’re doing a long-term strategy to slowly turn the legislature to become more friendly to them.”

Other companies, like Airbnb and Uber, have also donated to local assembly and senate races across the state but with smaller contributions.

City campaigns are seeing a tech infusion too. Joe Lonsdale, a Palantir co-founder, contributed to former reality TV star and Los Angeles mayor hopeful Spencer Pratt – even though Lonsdale lives in Texas, records show. And several 501(c)(4) groups backed by Silicon Valley money have cropped up across the Bay Area sending out mailers and robotexts with voter guides that highlight preferred local candidates, along with suggestions to vote down issues like a union-backed parcel tax.

“Now they’re going at this from multiple fronts,” Bennett said. “They’re spending in elections, they’re spending in the legislature, and they’re trying to do whatever they can to ensure that they don’t lose their foothold in this economic system.”

Lauren Gambino contributed reporting"

Tech billionaires are spending unprecedented sums in California races. Experts say it’s the tip of the iceberg | California | The Guardian

Middle East crisis live: Iran says no more peace talks with US until Israel stops its operations

Middle East crisis live: Iran says no more peace talks with US until Israel stops its operations

"Report from the IRGC-linked Tasnim news agency says talks on hold until Israel stops operations in Lebanon and Gaza

Cars sit in traffic on a highway as residents flee following an Israeli threat to strike Dahiyeh, Beirut's southern suburbs, Lebanon, Monday, June 1, 2026.
Cars sit in traffic on a highway as residents flee following an Israeli threat to strike Dahiyeh, Beirut's southern suburbs, Lebanon, Monday, June 1, 2026. Photograph: Bilal Hussein/AP

Iran says there will be no peace talks with the US until its demands on the cessation of Israeli operations in Lebanon and Gaza are met, according to the IRGC-affiliated Tasnim news agency.

Tasnim reported that Iran’s negotiating team is pulling out of message exchanges through mediators with the US over Israel’s offensive in Lebanon.

Tasnim further reported that Iran and what it called its “resistance front”, or proxies, will look to completely block the strait of Hormuz. It said it will also look to “activate” other fronts, including the Bab el-Mandem strait, which sits off the coast of Yemen, across the Arabian peninsula from the strait of Hormuz.

The Houthis, an Islamist armed group that controls large parts of Yemen, are allies of Iran – they have previously targeted shipping in the Red Sea and likely the “resistance” referred to by Iran in the statement.

French president Emmanuel Macron has said France is ready to support US-Iran ceasefire talks, following a phone call with US president Donald Trump last night.

In a post on X, the French president said: “Last night, I spoke with President Trump about the situation in the Middle East. I commended the determined efforts he is leading to quickly reach an agreement between the United States and Iran, which represents a unique opportunity to build a new security framework involving all concerned parties, in order to enable a lasting stabilization of the region.

“I indicated that we are ready to fully support these efforts and to take our full part in their implementation. This is the purpose of the international mission that we have built with the British and our partners, ready to be deployed as soon as an agreement is concluded in order to contribute to securing maritime traffic in the Strait of Hormuz.

“We are also prepared to bring our expertise and capabilities to the broader negotiations that must open, particularly on the nuclear aspect of an agreement. Finally, I commended President Trump’s commitment to the sovereignty and territorial integrity of Lebanon, and emphasized the importance of a robust ceasefire and our collective support for the Lebanese authorities.”

Yesterday France called for an emergency UN security council meeting following Israel’s stepped up offensive in Lebanon. That will take place later today."

Middle East crisis live: Iran says no more peace talks with US until Israel stops its operations

Trump Hits the Stalemate Phase of His Interventions in Gaza, Ukraine and Now Iran - The New York Times

Trump Hits the Stalemate Phase of His International Interventions, and It Stings

"In Ukraine, Gaza and now Iran, President Trump’s early declarations of easy wins have given way to harsh reality.

President Trump, wearing a blue suit and red tie, sits at a table, with America flags behind him.
One of President Trump’s close aides said recently that destroying nuclear sites from the air is what America does best, and that controlling political events in nations like Iran, Russia and Ukraine is what the United States does worst.Doug Mills/The New York Times

By David E. Sanger

David E. Sanger has covered five American presidents over four decades at the Times, and writes often on the revival of superpower conflict, the subject of his latest book.

President Trump likes his military and diplomatic victories quick, clean and decisive.

On his desk in the Oval Office, he keeps models of the B-2 bombers that took out three Iranian nuclear sites in one night, not quite a year ago. In the opening weeks of the Iran conflict this year, he talked often about replicating his success in Venezuela — “the perfect scenario,’’ he said — shorthand for overthrowing a troublesome leader with one quick commando raid, and replacing him with a pliant, American-friendly successor.

But now, Mr. Trump has hit the stalemate phase of his presidency.

The war with Iran is clearly at that stage. When he declared a cease-fire on April 7, Mr. Trump said on social media that the end of combat operations would be conditional on “the COMPLETE, IMMEDIATE, and SAFE OPENING of the Strait of Hormuz.” It wasn’t. Even if commerce now resumes across the strait under a memorandum of understanding still under negotiation, it will still leave the future of Iran’s nuclear and missile programs exactly where they were in February: stuck in a further negotiation that the administration insists will be “time limited,” probably to 60 days.

But the Iranians sense Mr. Trump’s deep reluctance to restart combat operations that are deeply unpopular in the United States, and most Iran experts say they expect Tehran to try to stretch the negotiations for months or years — as they have with past administrations.

Then there is the Ukraine war, a conflict in its fifth year that Mr. Trump famously boasted he would end in 24 hours after taking office. Sixteen months after he was sworn in, he rarely mentions the war anymore, and Secretary of State Marco Rubio recently complained that he was tired of wasting time in endless negotiations, suggesting that he would be perfectly happy if some other country wanted to step in and play that role.

For their part, the Russians have quietly made clear that they are tired of periodic visits from the president’s special envoy Steve Witkoff and Mr. Trump's son-in-law Jared Kushner, according to people familiar with the negotiations. They say they want a stable, diplomatic process, with working groups and regular meetings. They also want an American ambassador to Russia — a job that has been open, astoundingly, for nearly a year.

And there is Gaza. When Mr. Trump flew to Israel to celebrate the release of the last of the living hostages from the Oct. 7, 2023, terror attack, he enthused about a 20-point plan that started with the disarming of Hamas, the creation of an international stabilization force and, ultimately, rebuilding Gaza into a gleaming territory of glass office towers and seaside resorts. Eight months after that trip, Hamas has still not disarmed, except in fake, A.I.-generated videos. (One, sent out by Mr. Trump, depicts him and Prime Minister Benjamin Netanyahu sunbathing.)

While more aid is making its way into the territory, Palestinians are still sleeping in tents, the rat-infested rubble has not been cleared, and Mr. Netanyahu announced last week that the Israeli military would expand its control to about 70 percent of the Palestinian enclave.

Perhaps all of this is the inevitable result of a president with huge ambitions running into the brick walls of global realities. Perhaps it is the result of overreach, as Mr. Trump — infused with the success of his first two military adventures, into Iran and Venezuela — assumes that there is no task too big for the U.S. military.

Some experts suggest that it arises from a fundamental misunderstanding of American power. As one of Mr. Trump’s close aides said recently, destroying nuclear sites from the air is what America does best, and controlling political events in nations like Iran, Russia and Ukraine is what the United States does worst.

“Foreign policy tends to be a long and difficult enterprise,” Richard Fontaine, a former top aide to Senator John McCain and now the chief executive of the Center for a New American Security, said in an interview over the weekend. “Mr. Trump is not the first president to imagine quick, simple solutions to complicated and enduring international problems. Yet it is the sustained management and follow-through that often makes all the difference, not the grand and dramatic announcement.”

Follow-through has never been Mr. Trump’s strong suit. To establish his bona fides for a Nobel Peace Prize, he liked to gather testimonials to the breakthroughs he made or invite leaders at the White House and hold a signing ceremony; if fighting resumes, he is unlikely to dwell on the implications.

An exception is the Russia-Ukraine conflict, where Mr. Trump has episodically admitted he underestimated the complexity of the problem, and perhaps his powers of persuasion.

“I’ve had cases where I had Putin all done and Zelensky wouldn’t make the deal, which shocked me,” Mr. Trump said in an interview with The New York Times in January, referring to Presidents Vladimir V. Putin of Russia and Volodymyr Zelensky of Ukraine. “Then I’ve had cases where it was the reverse. I think now they both want to make a deal, but we’ll find out.”

In the nearly five months since that interview, Mr. Trump has repeatedly predicted a deal was near, and repeatedly it has fallen through. Today the Ukrainians feel more empowered. Their long-range drones and homemade missiles are reaching deep into Russian territory, striking critical energy sites, factories and laboratories that churn out key weapons components, and occasionally targets in Moscow. One of Britain’s intelligence chiefs, Anne Keast-Butler, said last week that nearly half a million Russian soldiers had been killed in a conflict that Mr. Putin thought would be over in weeks.

Yet Mr. Rubio, who left the negotiating chiefly to Mr. Witkoff and Mr. Kushner, sounded the other day as though he had given up on moving either side to a peace accord anytime soon. “The U.S. stands ready and prepared to help do whatever we can to help facilitate the end of this war,” he told reporters on Tuesday. “And hopefully the opportunity will present itself at some point that we can play that role again.”

To some experts who have been playing a behind-the-scenes role in trying to spur negotiations, the administration’s mistake has been relying too much on episodic phone calls or visits of special envoys, without the day-to-day engagement of traditional diplomacy to keep talks moving.

“This conflict is ripe for conclusion,” said Thomas Graham, a longtime American diplomat who served in Moscow before the collapse of the Soviet Union and managed a strategic dialogue with the Kremlin during the George W. Bush administration. “The mood has changed in Moscow. The battlefield is different: The Ukrainians have frozen the front line. The economic problems in Russia are building, and some political discontent is bubbling up. Conversations inside the Kremlin are on ‘How do we present this as a victory?’”

But he noted that “you have to have a negotiating process,” and that is still missing. “I think they would like to see the process institutionalized,” Mr. Graham added, “so it’s more than a couple of envoys talking to Putin.”

Iran is a particularly complex form of stalemate.

During the negotiations with Iran in Geneva in February, Mr. Witkoff said in an interview with Fox News that Mr. Trump was “curious as to why they haven’t — I don’t want to use the word ‘capitulated,’ but why they haven’t capitulated.”

Mr. Trump asked the same question in the opening weeks of the war. He declared that the only outcome acceptable to him would be an Iranian “unconditional surrender.”

None of that happened. When I asked Mr. Trump, on his flight back home from China in the middle of May, why he thought resuming military action would bring him any closer to his political goals than the first round of strikes had, he erupted with a list of targets hit by the military, and pointed to a devastated Iranian air force and navy, but never answered the question of why Iran never gave up its enriched uranium or its missile program. He called the Times, and me, “treasonous.”

That was two weeks ago. Now Mr. Trump is trying a mix of incentives, threats and revised demands to force the country into the kind of negotiation that was underway in February, when he and Mr. Netanyahu initiated the war.

“He tried to bomb Iran, he tried to blockade Iran, he tried to bully Iran, and he is stuck,” Jake Sullivan, the national security adviser to President Joseph R. Biden Jr., and a key player in the Obama-era negotiations with the country, said recently.

Should Mr. Trump and Iran’s clerical and military leadership agree to the accord, that would start a new round of negotiations that could stretch on.

“The narrower problem of ongoing Iranian enrichment was solvable through bombing, at least in the medium term,’’ Mr. Fontaine noted. “The broader problem of the Islamic Republic is not.”

Mr. Trump ran into similar discoveries in Gaza. There, he successfully brokered a truce between Israel and Hamas, and all hostages, both dead and alive, were released. But everything after that has stalled, and Mr. Trump lost focus as the Iran conflict consumed attention.

A new Palestinian administration, which Mr. Trump suggested would be in place in months, has not entered the territory to take charge of rebuilding the cities. Mr. Trump’s “Board of Peace,” which was supposed to oversee the rebuilding and investment effort, has barely gotten out of the starting gate. And Israel continues bombardments almost daily.

David E. Sanger covers the Trump administration and a range of national security issues. He has been a Times journalist for more than four decades and has written four books on foreign policy and national security challenges."

Trump Hits the Stalemate Phase of His Interventions in Gaza, Ukraine and Now Iran - The New York Times

Opinion | Marco Rubio: Florida Centrist, Tea Party Darling, MAGA Warrior, President? - The New York Times

How Long Can Marco Rubio Keep This Up?

Opinion Guest Essay

Celina Pereira

By Manuel Roig-Franzia

"Mr. Roig-Franzia was Miami bureau chief for The Washington Post and is the author of a biography of Mr. Rubio.

Nine days before Christmas in 1987, federal drug agents descended on a modest one-acre property in West Miami. Their target was a drug dealer named Orlando Cicilia, whom they arrested and charged with selling and distributing millions of dollars of Colombian cocaine. The raid against Mr. Cicilia and his associates would prove to be one of the biggest drug busts in Florida history. In retrospect, it was notable for one other fact: Mr. Cicilia was Marco Rubio’s brother-in-law.

Some of Mr. Rubio’s most vivid early experiences took place in the house where Mr. Cicilia was arrested. Mr. Rubio’s “fondest childhood memory” was of a Christmas Eve party where Mr. Cicilia roasted a pig in a pit covered with palm fronds in the yard of the house, according to Mr. Rubio’s memoir. Later, when Mr. Rubio wanted to buy season tickets to Miami Dolphins games, he earned money by washing his brother-in-law’s and sister’s dogs in the yard. He even lived in the house briefly while his parents were moving across the country.

Mr. Rubio has come a long way in the four decades since, rising to the role of global vanquisher of drug cartels and America First enforcer as President Trump’s secretary of state. Mr. Trump tapped Mr. Rubio to “run” Venezuela after the military operation to seize dictator Nicolás Maduro and bring him to the United States on drug trafficking charges in January. Mr. Rubio has said little over the years about his brother-in-law’s arrest, beyond noting the shock and heartbreak it caused his family.

The contrast between Mr. Rubio’s childhood relationship with a man who was later convicted of drug dealing and his current globe-trotting role might seem like one of those random biographical quirks that are more common in fiction than in real life. Yet understanding Mr. Rubio has always required reconciling such conflicting storylines. As a Florida legislator, he communed with migrant laborers and backed tuition discounts for children of undocumented immigrants, then became an immigration hard-liner when he ran for the United States Senate, then morphed again into a bipartisan immigration reformer in Congress.

The contradictions have only mounted in Mr. Rubio’s latter-day alliance with Donald Trump, and not just on the issue of immigration. Mr. Rubio has shifted from an impassioned champion of U.S. foreign aid to one of the dismantlers of the United States Agency for International Development. He has gone from piquant adversary of the president’s first-term foreign policy to an enabler of legally disputed strikes on alleged drug-trafficking boats and a cheerleader for the president’s hegemonic approach to the Western Hemisphere. Having lambasted President Barack Obama’s 2015 deal to ease sanctions on Iran in exchange for limits on its nuclear program, Mr. Rubio is now among the loudest supporters of a similar agreement that Mr. Trump hopes will end the war there.

Mr. Rubio’s gymnastics have made him an increasingly successful ally of the president and increasingly puzzling to those who thought he’d be a moderating, less MAGA-ish force within Trump 2.0. Yet his shape-shifting is not a new phenomenon; it is a defining characteristic. A close look at Mr. Rubio reveals one consistent truth about him: Marco Rubio has always found a way to belong.

In his Venezuela ascendancy and through his navigation of the failures of the Iran war, he has managed to deepen his relationship with Mr. Trump and cement his membership-in-good-standing in the political movement the president created. He has seemed just fine with going on television to defend Trump’s war of choice in Iran, when others, including his main rival to be Trump’s heir apparent, Vice President JD Vance, occupy more prominent public roles in negotiations to end the conflict. As when he was playing high school football, Mr. Rubio seems delighted to be on the team, even if he’s not a star player.

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That’s not to say Mr. Rubio won’t get his chances for glory. Mr. Trump frequently mentions him as the man who will bring Cuba into line with the president’s goal of regional domination. As the Iran war lumbers to an inconclusive end, that hemispheric goal is returning to Mr. Trump’s attention. On May 20, the Justice Department indicted the country’s former president, Raúl Castro, and a Trump-imposed oil blockade has triggered an economic crisis on the island. Mr. Rubio, for his part, has offered the country $100 million in aid via the Catholic Church or independent charities.

At some point, it seems as if Mr. Rubio’s pileup of contradictions will have to catch up with him. Yet over the two decades I have observed him, including writing a 2015 biography, Mr. Rubio’s paradoxes haven’t been a liability. If anything, they’ve been an asset, at least from a political perspective. Few are better at reading the American room. Which means Americans have a real interest in Mr. Rubio’s serial metamorphoses, not just because he is currently both secretary of state and national security adviser, but because he clearly still harbors ambitions of becoming president himself one day.

Born in Miami in 1971, Mr. Rubio spent hours at the side of his beloved grandfather, Pedro Víctor García, listening to the family’s stories. In many ways, they were familiar tales of an immigrant family new to America. Mr. García had come to the United States in 1956 from Cuba in search of a better life. In 1962, after an extended stay abroad, an American immigration judge ruled that Mr. García had relinquished his legal resident status. The judge ordered Mr. García deported, according to a recording of the proceeding. The order was issued shortly before the Cuban Missile Crisis threw relations between the countries into chaos, however, and Mr. García ended up staying in the U.S. for good.

In the ensuing years, the American dream did not come easily to the Rubio family. Mr. Rubio’s father, who had arrived in the United States in 1956 before the start of the Cuban revolution, struggled to earn a living, tending bar and managing a residential building near Miami’s airport. They did find community in religion. The Rubios belonged to a neighborhood Catholic church in Coral Gate, west of Little Havana. The young Mr. Rubio delighted in dressing up like a priest after Mass. “I had a habit as a child of playacting scenes from experiences that had made an impression on me,” Mr. Rubio wrote in his memoir.

In 1979, when he was 8, the family left behind a Miami roiling with drug-cartel violence and moved to Las Vegas, where an aunt of his would factor heavily into his life. The aunt was Mormon. So were the neighbor boys next door. He wanted to be Mormon, too. To entertain himself and his family, he would lip-sync the songs of the Mormon television stars, Donny and Marie Osmond. Soon enough, he and his mother were baptized into the Church of Jesus Christ of Latter-day Saints. The conversion was short-lived: in 1984, the family moved back to Florida and by the time Mr. Rubio was in high school, his family had followed him back to Catholicism.

They embraced the intense and ever-present anti-Castro, Cuban exile atmosphere of Miami. That would become an abiding hallmark of Mr. Rubio’s political identity. Ascending from his days as a 20-something member of a suburban Miami city commission to become the first Cuban American speaker of the Florida House, Mr. Rubio was propelled in part by the power of a story he recounted about his family. He told the Cuban Americans among the audiences for his speeches that he was one of them — a son of exiles whose parents were forced to leave Cuba by Fidel Castro.

It was a story that turned out to be inaccurate. While researching my biography of Mr. Rubio, I came upon documents that proved his parents and older brother had arrived in the United States before the Cuban revolution began — nearly three years before Castro took power, around the same time as Mr. Rubio’s grandfather. In fact, his grandfather had returned to Cuba after Castro’s ascent and taken a menial transportation job in the government.

When I wrote an article about the discrepancy for The Washington Post, where I was a reporter at the time, Mr. Rubio said he had relied on the oral history of his family and that was what his parents had told him. He denied purposefully telling an inaccurate story for political gain. He said his parents should be considered exiles because they’d wanted to return to Cuba, but couldn’t. It was a fair point, even if it didn’t exactly clean up the story he’d been telling.

Soon enough, Mr. Rubio would face uglier challenges to his family’s history. When Mr. Rubio was a Republican vice-presidential contender in 2012, a theory began circulatingthat he was not a “natural-born citizen.” The argument went that his parents, though they were legally in the United States, were not U.S. citizens when he was born and that he would therefore not be eligible to become president someday.

It was a bogus attack — because he was born in the United States, Mr. Rubio has been a lifelong citizen. But in 2016, while running for president, the storyline resurfaced in a court case. As The New York Times’s Adam Liptak reported last year, Mr. Rubio felt compelled to file papers in which he made a full-throated defense of birthright citizenship.

As one of the first acts of his second term, Mr. Trump issued an executive order greatly expanding the categories of people born in the United States who would not be eligible for birthright citizenship. The order has been stalled by court challenges, and in arguments before the Supreme Court in April, Mr. Trump’s case seemed headed for defeat. Whatever the result, Mr. Rubio and his family would not be affected. Mr. Rubio has embraced Trump’s move.

Despite all the contradictions, Mr. Rubio has cemented his membership in Mr. Trump’s MAGA movement. He has flipped from ardent support for Ukraine to an inclination to make concessions to the Russian strongman Vladimir Putin. He has abandoned his longtime support for the work of U.S.A.I.D. and is now instead presiding over its death.

Some of Mr. Rubio’s changes cut particularly close to home. His hard line on punishment for drug offenders contrasts with the leniency he once showed his former drug dealer brother-in-law, according to documents I unearthed with my then-Washington Post colleague, Scott Higham. When he was the majority whip of the Florida House of Representatives, Mr. Rubio used his official stationery to recommend to the Florida Division of Real Estate that Mr. Cicilia, who had recently been released from prison, should be granted a real estate license. The recommendation letter didn’t mention his personal relationship to Cicilia. (At the time, Rubio dismissed suggestions that he did anything unethical.)

Mr. Rubio is one of the few politicians who have survived crossing swords with Mr. Trump — so far. Mr. Trump won’t be president forever, and Mr. Rubio’s relationship with him and the movement he created is something the secretary of state will never be able to hide. Together they have embarked on building a world order that will be difficult, if not impossible, to undo: a go-it-alone, interventionist America that takes what it wants. From Venezuela to Iran, and now Cuba, Mr. Rubio is along for Mr. Trump’s disruptive ride. What if it all goes wrong?

I can imagine Mr. Rubio nimbly rising from the ashes, just as he did when Mr. Trump humiliated him in his home state of Florida by trouncing him in the 2016 presidential primary. I have no doubt Mr. Rubio is simultaneously relishing and feeling conflicted when he is, once again, trying on a new persona — a Trumpian MAGA role that he might one day need to abandon. The now-famous photographs of him on the Oval Office sofa watching Mr. Trump berate Ukraine’s Volodymyr Zelensky have become memes for good reason, capturing both his tough-guy frown and his discomfort as he shrinks into the pillows.

Yet it says a lot about Mr. Rubio’s skills that in the small group of shape-shifting survivors close to Trump, the secretary of state is emerging as a top contender in the race to succeed him. This new iteration of Mr. Rubio is angrier and more sullen than the often-sunny politician who became the charming and precocious darling of the Republican Party in the 2010s. His tone has become strident; his words, more biting. For now, at least, he’s sending a clear message to the MAGA world that he is one of them — and would be a fitting heir.

Manuel Roig-Franzia is the author of “The Rise of Marco Rubio,” and a former Washington Post bureau chief in Miami and Latin America.

Source photographs by SAUL LOEB/Getty Images

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Opinion | Marco Rubio: Florida Centrist, Tea Party Darling, MAGA Warrior, President? - The New York Times

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