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Trump’s Frustration With Generals Led to Picking Dan Caine for Joint Chiefs Chairman

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Trump’s Frustration With Generals Led to Picking Dan Caine for Joint Chiefs Chairman

By late last week, President Trump had decided to fire Gen. Charles Q. Brown Jr., the chairman of the Joint Chiefs of Staff, and replace him with one of two very different candidates, according to two administration officials.

One was Gen. Michael E. Kurilla, a hard-charging Army four-star general who oversees U.S. military operations in the Middle East, one of the Pentagon’s highest-profile assignments.

The other was a little-known retired three-star Air Force officer, Dan Caine, with an unorthodox career path that included time as a fighter pilot, the top military liaison to the C.I.A. and an Air National Guard officer who founded a regional airline in Texas.

Mr. Trump and General Caine met for an hour at the White House on Feb. 14. The president largely made up his mind during a meeting with Defense Secretary Pete Hegseth on Thursday, aides said.

And in a message on social media the next evening, Mr. Trump announced that he had picked General Caine, calling him “an accomplished pilot, national security expert, successful entrepreneur, and a ‘warfighter’ with significant interagency and special operations experience.”

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The decision, part of an extraordinary purge at the Pentagon, resulted from intense deliberations over the past two weeks that were tightly held within a small group of senior administration officials, including Mr. Hegseth, Vice President JD Vance and Michael Waltz, the national security adviser, the officials said, speaking on the condition of anonymity to discuss internal discussions.

In Mr. Trump’s first term, he initially seemed to seek a close association with the military’s senior leaders, whom he frequently referred to as “my generals.” That soon gave way to frustration with them as he came to regard them as disloyal.

The president’s deep skepticism prompted him to pass over the more obvious choices, like General Kurilla, to replace General Brown and to pluck General Caine from relative obscurity. His choice, people familiar with his thinking said, was based in part on General Caine’s lack of clear association with the Biden administration and in part on a brief encounter with the general in Iraq six years ago that left Mr. Trump convinced he had the kind of can-do attitude the president sees as making the ideal military officer.

In recent years, Mr. Trump has publicly praised General Caine for telling him during that visit to Iraq that the Islamic State could be defeated far more quickly than more senior advisers had suggested.

Now their rekindled relationship will be tested not only by national security challenges like the war in Ukraine and a rising military threat from China, but also by whether General Caine can live up to Mr. Trump’s expectations of loyalty without politicizing the deliberately apolitical job of providing his best military advice to the commander in chief.

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Mr. Trump has fixated on the position of the Joint Chiefs chairman since 2019, when he picked Gen. Mark A. Milley, General Brown’s predecessor. It was a decision the president came to regret.

The president saw General Milley as a grandstander and a traitor. General Milley had publicly apologized for walking with Mr. Trump across Lafayette Square for a photo op after the area had been cleared of peaceful demonstrators following the death of George Floyd in May 2020. The president had asked General Milley why he was not proud that he had accompanied “your president,” and it rankled Mr. Trump that the general swore allegiance to the Constitution, not to him. Their relationship was never the same.

“Trump likes his generals up until the point he doesn’t anymore,” John R. Bolton, the national security adviser in Mr. Trump’s first term, said in an interview.

After Mr. Trump was elected to a second term, word soon spread that he would replace General Brown, a decorated F-16 fighter pilot who in October 2023 became only the second African-American to serve as chairman.

After Mr. Hegseth was narrowly confirmed as defense secretary last month, that likelihood became a near certainty, administration officials said. Mr. Hegseth had previously said General Brown should be fired because of what he called a “woke” focus on diversity, equity and inclusion programs in the military. Mr. Hegseth also questioned whether the general was promoted because of his race, despite his 40 years of service.

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Several weeks ago, the search for a new chairman began in earnest, administration officials. Adm. Samuel J. Paparo Jr., the head of U.S. forces in the Indo-Pacific, was briefly considered, among several other initial candidates.

But the list of finalists quickly shortened to General Kurilla and General Caine.

On paper and in conventional thinking, General Kurilla seemed to have the leg up. He was meeting regularly with Mr. Trump and other top national security aides to discuss military priorities in the Middle East. Moreover, General Kurilla, whose tenure at Central Command is expected to wrap up in the next few months, had expressed interest in the job, several current and former military officials said. In the end, General Kurilla seemed too similar to the officers whom Mr. Trump had soured on, aides said.

General Caine, on the other hand, had retired at the end of December after completing the final job in his military career — as the Pentagon’s liaison to the C.I.A. — and joined Shield Capital, a firm in Burlingame, Calif., specializing in cybersecurity and artificial intelligence.

General Caine, 56, who graduated from the Virginia Military Institute in 1990 with a degree in economics, became an F-16 pilot — as his father had been — and was the lead aviator assigned to protect Washington on Sept. 11, 2001, after Qaeda hijackers slammed commercial jets into the Pentagon and the World Trade Center.

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His career after that followed an unusual trajectory, as he parlayed one opportunity into another, picking up valuable new skills at each stop as well broadening his vast network of contacts. He was a White House fellow at the Agriculture Department and a counterterrorism specialist on the White House’s Homeland Security Council under President George W. Bush. He served in several highly secretive intelligence and special operations assignments, some in the United States and some overseas, all rare for an Air National Guard officer.

As a part-time Guard officer, General Caine was a co-founder of RISE Air, a regional airline, and managed other private businesses, according to his LinkedIn page and interviews with friends and former colleagues. In his C.I.A. job, he was keenly interested in the intersection of technology and national security, and kept close tabs on American companies that sold cutting-edge technology to Ukraine in its fight against Russia.

But what put him on Mr. Trump’s radar was the president’s short visit to Al Asad air base in western Iraq in late December 2018. In a briefing there, General Caine told the president that the Islamic State was not so tough and could be defeated in a week, not the two years that senior advisers predicted, Mr. Trump recounted in 2019.

And at a Conservative Political Action Conference meeting last year, Mr. Trump said that General Caine put on a Make America Great Again hat while meeting with him in Iraq.

The details of these accounts have shifted over time in Mr. Trump’s frequent retelling of the stories. But Mr. Bolton, who accompanied Mr. Trump on the trip to Iraq, said that General Caine and another senior general briefed the president on a plan to defeat the last remnants of the Islamic State in two to four weeks, not one week. And at no time, he said, did General Caine ever put on a MAGA hat. “No way,” Mr. Bolton said.

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In his social media message, Mr. Trump also noted General Caine’s nickname, “Razin,” recalling Mr. Trump’s obsession with former Defense Secretary Jim Mattis’s nickname, “Mad Dog,” a moniker Mr. Mattis hated.

General Caine’s nickname embodied the kind of hell-raiser warrior straight out of central casting that Mr. Trump was looking for in his top general, officials said. He fulfilled a fantasy vision the president has of what generals do, they added.

In his post on Friday, Mr. Trump again praised General Caine’s counterterrorism skills. “During my first term, Razin was instrumental in the complete annihilation of the ISIS caliphate,” the president said. “It was done in record setting time, a matter of weeks. Many so-called military ‘geniuses’ said it would take years to defeat ISIS. General Caine, on the other hand, said it could be done quickly, and he delivered.”

Mr. Trump revealed another reason for his unconventional choice. He said that General Caine had been passed over for promotion by President Joseph R. Biden Jr., a claim that Biden officials said on Sunday they could not address. Aides say that in Mr. Trump’s mind, that perceived snub was a great endorsement, proof that General Caine has no specific loyalty to the previous administration. To Mr. Trump, who views most senior officers as incompetent and politically correct, it also suggests that General Caine has a different mind-set.

Friends and former colleagues say that General Caine, an intensely focused but low-key, self-effacing officer despite his nickname, has been uncomfortable with Mr. Trump’s characterization of his role in defeating the Islamic State. Friends who have known him for decades say they have no idea what his political affiliation is, explaining that the general does not talk about politics. General Caine did not respond to emails requesting comment on Sunday.

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But when the White House called a couple of weeks ago as he was preparing to move to Dallas from Washington, friends of General Caine say, he did not hesitate to accept the meetings with Mr. Trump and his top aides, and ultimately the job — out of duty to the country.

Which raises perhaps the most important question for General Caine as he prepares to return to active duty as soon as this week, and get ready for what is expected to be a tough Senate confirmation hearing: Will he give his best unvarnished military advice to Mr. Trump, or tell the president what he wants to hear?

“He was always direct and candid in the interagency, which is no small feat,” Gen. Kenneth F. McKenzie Jr., a former head of Central Command who dealt frequently with General Caine in his C.I.A. job, said on Sunday. “I never saw him as a yes-man.”

Senator Jack Reed of Rhode Island, the senior Democrat on the Armed Services Committee, said in an interview on Sunday that he would press General Caine in his hearing on that central point: “Will he have the ability to speak truth to power?”

Jonathan Swan, Maggie Haberman and Helene Cooper contributed reporting.

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Rubio sanctions Cuban groups with ties to US nonprofit network funded by communist donor Neville Roy Singham

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Rubio sanctions Cuban groups with ties to US nonprofit network funded by communist donor Neville Roy Singham

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Secretary of State Marco Rubio put U.S. organizations on notice: they can no longer do business with a key Cuban organization that has spent over six decades – since the launch of Fidel Castro’s communist revolution in 1959 – cultivating relationships with U.S. activists and groups, many of them now funded by communist American tycoon Neville Roy Singham.

The sanctions target the Cuban Institute of Friendship with the Peoples, known by its Spanish acronym ICAP, an organization founded by Castro in 1960 to spread Marxist ideology and support for Cuba. Long ago, U.S. officials and intelligence assessments concluded ICAP is a key component of Cuba’s intelligence apparatus.

“For decades, Cuba has been the world capital for radical left-wing terrorism,” Rubio said. “The regime in Havana has recruited, trained and backed violent Marxist and third-worldist movements across our hemisphere and beyond.”

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Marco Rubio moves to put sanctions on a group that Fidel Castro established in 1960 to spread Cuba’s communist influence in the world. (Sven Creutzmann/Mambo Photography/Getty Images; Nathan Posner/Anadolu via Getty Images)

Earlier this year, ICAP worked with U.S. nonprofits, including the People’s Forum, Progressive International and CodePink, to organize a March “convoy” that included controversial Marxist streamer Hasan Piker landing in Cuba to support Cuba’s communist party.

The trip has since attracted federal scrutiny, with CodePink co-founder Medea Benjamin confirming she received questions from federal officials about the trip, investigating whether she violated sanctions.

Late last month, Fox News Digital published a three-part series, reporting that federal investigators are examining Cuba’s alleged malign foreign influence operation in the U.S., investigating a network of 145 groups with collective revenues of about $1 billion, promoting Cuba’s agenda and communist ideology.

“Today, we are targeting the network that enables and funds Cuba’s subversive and radical operations,” Rubio said.

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The groups working closely with ICAP include the People’s Forum, CodePink, BreakThrough News and Tricontinental, funded by Singham, a Marxist tech tycoon living in Shanghai. As reported, Singham has pumped $285 million into nonprofits since 2017 that have built very close relationships with ICAP and the communist government of Cuba.

Singham is married to CodePink co-founder Jodie Evans.

INSIDE CUBA’S FOREIGN INFLUENCE CAMPAIGN: FROM THE VENCEREMOS BRIGADE OF THE 1960S TO SATURDAY IN A UNION HALL

ICAP is today led by Fernando González Llort, one of five former Cuban intelligence officers, known as the “Cuban Five,” convicted in the U.S. years ago on espionage-related charges and released after spending time in jail. 

Critics say ICAP acts as a gateway for revolutionaries from around the world to get embedded in the propaganda, organizing tactics and strategic goals of the Communist Party of Cuba. ICAP has denied wrongdoing and says it’s a civil society organization.

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ICAP was one of five entities that Rubio designated as off-limits under sanctions authorities established by President Donald Trump’s Cuba executive order. The sanctions also target Cuba’s Ministry of the Revolutionary Armed Forces (MINFAR), the Committees for the Defense of the Revolution (CDR), Minera La Victoria S.A. and the state-run tourism company Amistur Cuba S.A., which has arranged trips to Cuba with U.S. nonprofits in the Singham network.

Experts said the move signals that the Trump administration is focused not only on the Cuban government but also on U.S. institutions that U.S. officials believe help project Cuban influence internationally.

A declassified CIA report from the Cold War era, “Cuba: Castro’s Propaganda Apparatus and Foreign Policy,” described Cuba’s international propaganda and influence activities as a central component of Castro’s foreign policy strategy. The report named ICAP among organizations that act as important instruments for cultivating sympathetic political movements abroad and extending Cuban influence beyond the island.

DOJ, TREASURY INVESTIGATE NONPROFITS AND LEADERS ALLEGEDLY COORDINATING WITH CUBA IN INFLUENCE CAMPAIGN

One of the most notable examples was the Venceremos Brigade, a Cuba solidarity program established in 1969 that brought generations of American activists to the island through exchanges organized with Cuban authorities and institutions including ICAP.

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The program became one of the most visible pipelines connecting American activists to the Cuban revolutionary government.

Today, the Venceremos Brigade operates as a fiscally-sponsored project of the People’s Forum.

Lawmakers and federal authorities are examining whether organizations funded by Singham have acted on behalf of foreign interests without properly registering and have helped amplify messaging favorable to the Chinese Communist Party and the Communist Party of Cuba.

Cuba’s President Miguel Diaz-Canel (C) listens to Progressive International’s general coordinator, David Adler, during an event at the Cuban Institute for Friendship with the Peoples (ICAP) in Havana, on March 21, 2026. (Ernesto Mastrascusa/AFP via Getty Images)

HOW A RHODES SCHOLAR WITH TIES TO CUBA’S PRESIDENT ORGANIZED THE CONVOY THAT BROUGHT HASAN PIKER TO HAVANA

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During the recent convoy in March, Progressive International co-founder David Adler appeared alongside Cuban President Miguel Díaz-Canel and ICAP President González at an official event hosted by ICAP.

Years ago, Los Angeles Mayor Karen Bass participated in Venceremos Brigade trips, a connection that her mayoral candidate Spencer Pratt resurfaced during her campaign. Bass has denied any wrongdoing.

Supporters of such exchanges describe them as educational and humanitarian programs intended to foster international understanding. Critics argue they function as political influence operations designed to build support for the Cuban regime and its ideological objectives.

The Cuban government condemned Rubio’s sanctions shortly after the announcement.

President Miguel Díaz-Canel accused the United States of escalating economic pressure against Cuba and attempting to intensify tensions between the two countries.

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Hasan Piker, a Democratic Socialists of America member, and CodePink co-founder Jodie Evans meet in Havana, Cuba, as part of a “United Front” supporting the communist regime. (CodePink via Storyful)

“The Treasury Department has added new names of Cuban leaders, organizations and companies to an illegitimate sanctions list,” Díaz-Canel wrote on social media. “They are aimed at reinforcing the blockade measures and the scenario of conflict between Cuba and the United States.”

Rubio’s warning extended beyond the sanctioned entities.

The action signals that the administration is increasingly focused on the networks, partnerships and influence channels that U.S. officials believe have helped advance Cuban interests abroad long after the Cold War officially ended.

“Anyone providing services to these sanctioned actors is at risk of sanctions themselves,” he said. “Foreign banks and other companies that provide services to these entities should freeze those activities.”

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Fox News Digital’s Reagan Schroeder contributed to this report.

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Commentary: No, Mr. Hilton, our elections are not ‘a joke.’ It’s time for you to stand up to Trump

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Commentary: No, Mr. Hilton, our elections are not ‘a joke.’ It’s time for you to stand up to Trump

Well, that didn’t take long.

A day after California’s primary election, President Trump took to social media with baseless claims of election fraud — predictable, but also dangerous.

“Look what’s happening in California, the Dumocrats, right before our very eyes, are stealing the Vote,” Trump wrote in one post.

“There’s BIG cheating by the Dumocrats in California,” he wrote in another, apparently enamored of his latest juvenile slur.

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Never mind that his candidate, Steve Hilton, is in the lead — for now anyway.

California has once again become the main dish on Trump’s buffet of bull-hockey as he continues to undermine democracy and consolidate authoritarian power, using this disingenuous and patently untrue narrative that American elections are rigged by shadowy Democratic forces working in collusion with illegal immigrants.

That last part is called the Great Replacement Theory, the idea that “elites” are replacing white people — and white voters — with Black and brown immigrants in a bid to destroy white culture. It’s at the heart of Trump’s voter fraud allegations.

The twist this time is that Hilton, the man who wants to represent all Californians, seems to be jumping on the election fraud conspiracy train with the president. I get it, there’s the MAGA base to feed, and it’s a base that feasts on outrage and fakery. Serving up resentment glazed with lies and propaganda has been the MAGA playbook for years under Trump, a strategy that no one can deny has been heartbreakingly effective.

But Hilton is a smart man and must certainly know that voter fraud is rare, to the point of being inconsequential to election outcomes. Hilton by his own admission understands voting patterns, and that in this cycle, Republicans have voted early and often by mail, despite Trump’s claims that all vote-by-mail should be suspect. So Hilton understands that early votes have skewed his way, and that later vote tallies will likely favor Democrats.

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And Hilton is definitely intelligent enough to expect that in a state where Democrats outnumber Republicans nearly three to one, he will not keep the top spot in this primary, and a slim chance remains that he will not make it into the top two. That’s just simple math.

So if Hilton truly seeks to represent this state as its top elected executive, now is the time to renounce election fraud myths and stand up to Trump’s lies. If Hilton can’t say that he believes our recent election was free and fair, then he has no business being our governor.

Unfortunately, that doesn’t seem to be the path he’s taking, even as it seems increasingly likely that he will advance to the general election.

This week, speaking with far-right podcaster and former Turning Point USA creative director Benny Johnson (who was allegedly duped into working for a Russian influence operation), Hilton said that while “so far we’re not seeing any signs” of cheating, “we’re going to be all over it. We’re not going to let them do that.”

Hilton was responding to a question from Johnson on whether Hilton will sue over “cheating.”

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On a post-election appearance with Laura Ingraham, the conservative Fox News host who has repeatedly promoted the Great Replacement Theory, Hilton delved into more conspiracy.

“Just to really underline the point that you made about the corruption,” he told Ingraham an anecdote about supposed fraud in a previous election cycle when a “whistleblower” at the post office told him that they were instructed that a handwritten postmark was acceptable when sorting ballots to deliver to the county registrar.

“It’s just unbelievable, and of course, that’s why so many people don’t believe the results, but it just undermines confidence,” he told Ingraham, certainly knowing that the post office forwarding a ballot on to a county registrar in no way means it will be certified or counted. Would we really want the USPS deciding which ballots to deliver? Disingenuous on Hilton’s part at best.

“The whole thing is a joke,” Hilton went on to say of California elections, which of course, is absurd.

Thursday, when I asked Hilton’s team to speak with him about his views on voter fraud, they sent back a response that focused on the slowness of the California vote count; voter rolls Hilton has described as “wildly inaccurate,” which is a wildly inaccurate claim; and two instances of actual fraud with voter registration — not examples of votes that were counted.

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To be sure, all those items are important. Any malfeasance should be punished, and the system should always strive to improve.

But how hard is it to simply be against fraud, while accurately acknowledging that it is rare and our current system provides accurate results?

I am against voter registration fraud. I am against vote fraud. I am absolutely pro-democracy, including policies such as mail-in voting that increase participation.

I do not believe that there is widespread fraud in the California primary, or in American elections in general, because the evidence does not support that conspiracy. I do not believe that Democrats are running a decades-long, nationwide conspiracy to replace white voters with votes from Black and brown undocumented immigrants, because that is both false and racist.

Pretty basic stuff, and statements in line with the values and common sense of the majority of Californians Hilton says he will represent.

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If Hilton can’t come out and clearly say that Trump is wrong — about fraud and about the Great Replacement Theory — can he really be trusted to represent the values of the Golden State?

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Video: Jan. 6 Rioter Hired by Pentagon

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Video: Jan. 6 Rioter Hired by Pentagon

new video loaded: Jan. 6 Rioter Hired by Pentagon

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Jan. 6 Rioter Hired by Pentagon

Elias Irizarry, who pleaded guilty to climbing through a broken window at the Capitol on Jan. 6, 2021, now works for an office responsible for uncovering and defending against terrorism plots at the Pentagon.

“Full pardon or commutation?” “Full pardon.”

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Elias Irizarry, who pleaded guilty to climbing through a broken window at the Capitol on Jan. 6, 2021, now works for an office responsible for uncovering and defending against terrorism plots at the Pentagon.

By Alisa Shodiyev Kaff

June 4, 2026

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