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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 targets Nicaraguan official over alleged torture tied to ‘brutal’ Ortega regime

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Rubio targets Nicaraguan official over alleged torture tied to ‘brutal’ Ortega regime

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Secretary of State Marco Rubio announced Saturday that the Trump administration is sanctioning a senior Nicaraguan official over alleged human rights violations.

Rubio said the U.S. is designating Vice Minister of the Interior Luis Roberto Cañas Novoa for his role in “gross violations of human rights” under the government of President Daniel Ortega and Vice President Rosario Murillo, marking what he said was the latest effort to hold the regime accountable.

“The Trump administration continues to hold the Murillo-Ortega dictatorship accountable for brutal human rights violations against Nicaraguans,” Rubio said in a post on X. “I’m designating Nicaraguan Vice Minister of the Interior Luis Roberto Cañas Novoa for his role in human rights violations.”

RUBIO TESTIFIES IN TRIAL OF EX-FLORIDA CONGRESSMAN ALLEGEDLY HIRED BY MADURO GOVERNMENT TO LOBBY FOR VENEZUELA

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Secretary of State Marco Rubio speaks at the State Department, April 14, 2026. The U.S. announced sanctions on a Nicaraguan official tied to alleged human rights abuses under the Ortega-Murillo government. (Andrew Harnik/Getty Images)

The designation was made under Section 7031(c), which allows the State Department to bar foreign officials and their immediate family members from entering the United States due to involvement in significant corruption or human rights abuses.

The State Department has said the Ortega-Murillo government has engaged in arbitrary arrests, torture and extrajudicial killings following mass protests that began in April 2018.

“Nearly eight years ago, the Rosario Murillo and Daniel Ortega dictatorship unleashed a brutal wave of repression against Nicaraguans who courageously stood against the regime’s increased tyranny, corruption, and abuse,” the statement reads.

The State Department said that the sanction marked the anniversary of the 2018 protests, after which more than 325 protesters were murdered in the aftermath.

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A panel of U.N.-backed human rights experts previously accused Nicaragua’s government of systematic abuses “tantamount to crimes against humanity,” following an investigation into the country’s crackdown on political dissent, according to The Associated Press.

The experts said the repression intensified after mass protests in 2018 and has since expanded across large parts of society, targeting perceived opponents of the government.

TRUMP ADMIN ANNOUNCES EXPANSION OF VISA RESTRICTION POLICY IN WESTERN HEMISPHERE

Nicaragua President Daniel Ortega delivers a speech during a ceremony to mark the 199th Independence Day anniversary, in Managua, Nicaragua Sept. 15, 2020.   (Nicaragua’s Presidency/Cesar Perez/Handout via Reuters)

Nicaragua’s government has rejected those findings.

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The designation follows a series of recent U.S. actions targeting the Ortega-Murillo government. In February, the State Department sanctioned five senior Nicaraguan officials tied to repression, citing arbitrary detention, torture, killings and the targeting of clergy, media and civil society.

Earlier this week, the department also announced sanctions on individuals and companies linked to Nicaragua’s gold sector, including two of Ortega and Murillo’s sons, accusing the regime of using the industry to generate foreign currency, launder assets and consolidate power within the ruling family.

The State Department said the move is part of ongoing efforts to hold the Nicaraguan government accountable for its actions.

Fox News Digital reached out to the Nicaraguan government and its embassy in Washington for comment but did not immediately receive a response.

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A man waves a Nicaraguan flag during a demonstration to commemorate Nicaragua’s national Day of Peace, which is celebrated in the country on April 19, and to protest against the government of Nicaraguan President Daniel Ortega in San Jose, Costa Rica on April 16, 2023. (Jose Cordero/AFP)

The Trump administration has taken an increasingly aggressive posture in the Western Hemisphere in recent months, including a Jan. 3, 2026, operation that resulted in the capture of Venezuelan leader Nicolás Maduro and his wife, Cilia Flores.

The U.S. has also carried out a series of strikes targeting suspected drug-trafficking vessels in the region, part of a broader crackdown tied to regional security and narcotics enforcement efforts.

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Outlines of a deal emerge with major concessions to Iran

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Outlines of a deal emerge with major concessions to Iran

Upbeat claims from President Trump over an imminent peace deal to end the war with Iran were met with deep skepticism Friday across the Middle East, where Iranian and Israeli officials questioned the prospects for a lasting agreement that would satisfy all parties.

The outlines of an agreement began to emerge that would provide Iran with a major strategic victory — and a potential financial windfall — allowing the Islamic Republic to leverage its control over the Strait of Hormuz to exact significant concessions from the United States and its ally Israel as Trump presses for a swift end to the conflict.

In a series of social media posts and interviews with reporters, Trump announced that the strait was “fully open,” vowing Tehran would never again attempt to control it. But Iranian officials and state media said that conditions remained on passage through the waterway, including the imposition of tolls and coordination with the Islamic Revolutionary Guard Corps.

Iranian diplomats posted threats that its closure could resume at any time of their choosing, and warned that restrictions would return unless the United States agreed to lift a blockade of its ports. Trump had said Friday that the blockade would remain in place.

“The conditional and limited reopening of a portion of the Strait of Hormuz is solely an Iranian initiative, one that creates responsibility and serves to test the firm commitments of the opposing side,” said a top aide to Iran’s president, dismissing Trump’s statements on the contours of a deal as “baseless.”

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“If they renege on their promises,” he added, “they will face dire consequences.”

In an overture to Iran, Trump said Israel would be “prohibited” from conducting additional military strikes in Lebanon, where the Israeli government of Prime Minister Benjamin Netanyahu seeks to prevent Hezbollah, an Iranian proxy militia, from rearming, a potential threat to communities in the Israeli north.

But in a speech delivered in Hebrew, Netanyahu would say only that Israel had agreed to a temporary ceasefire, while members of his Cabinet warned that Israel Defense Forces operations in southern Lebanon were not yet finished. A top ally of the prime minister at a right-wing Israeli news outlet warned that Trump was “surrendering” to Iran in the talks.

It was a day of public messaging from a president eager to end a war that has proved historically unpopular with the American public, and has driven a rise in gas prices that could weigh on his party entering this year’s midterm elections.

Yet, Republican allies of the president have begun warning him that an agreement skewed heavily in Tehran’s favor could carry political costs of its own.

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Trump was forced to deny an Axios report Friday that his negotiating team had offered to release $20 billion in frozen Iranian assets in exchange for Tehran agreeing to hand over its fissile material, buried under rubble from a U.S. bombing raid last year.

That sum would amount to more than 10 times what President Obama released to Iran under a 2015 nuclear deal, called the Joint Comprehensive Plan of Action, that was the subject of fierce Republican criticism in the decade since.

“I have every confidence that President Trump will not allow Iran to be enriched by tens of billions of dollars for holding the world hostage and creating mayhem in the region,” said Sen. Lindsey Graham (R-S.C.), a strong supporter of the war. “No JCPOAs on President Trump’s watch.”

Still, Trump said in a round of interviews that a deal could be reached in a matter of days, ending less than two weeks of negotiations.

He claimed that Tehran had agreed to permanently end its enrichment of uranium — a development that, if true, would mark a dramatic reversal for the Islamic Republic from decades developing its nuclear program, and from just 10 days ago, when Iranian diplomats rejected a U.S. proposal of a 20-year pause on domestic enrichment in favor of a five-year moratorium.

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He said Iran had agreed never to build nuclear weapons — a pledge Tehran has made repeatedly, including under the Nuclear Nonproliferation Treaty, in a religious decree from then-Supreme Leader Ayatollah Ali Khamenei, and in the 2015 agreement — while continuing nuclear activities viewed by the international community as exceeding civilian needs.

And he repeatedly stated that Iran had agreed to the removal of its enriched uranium from the country, either to the United States or to a third party. Iranian state media stated Friday afternoon that a proposal to remove the country’s highly enriched uranium had been “rejected.”

Iran’s agreement to allow safe passage for commercial vessels through the Strait of Hormuz is linked to a ceasefire in Lebanon that the Israeli Cabinet approved for only a 10-day period. Regardless of whether it holds or is extended, Israeli officials said their military would not retreat from its current positions in southern Lebanon — opening up Israeli forces to potential attack by Hezbollah militants unbound by a truce brokered by the Lebanese government.

The Lebanese people, Hezbollah officials said, have “the right to resist” Israeli occupation of their land. Whether the fighting resumes, the group added, “will be determined based on how developments unfold.”

An Iranian official threw cold water on the prospects of reaching a comprehensive peace deal in the coming days, telling Reuters that a temporary extension of the current ceasefire, set to expire Tuesday, would “create space for more talks on lifting sanctions on Iran and securing compensation for war damages.”

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“In exchange, Iran will provide assurances to the international community about the peaceful nature of its nuclear program,” the official said, adding that “any other narrative about the ongoing talks is a misrepresentation of the situation.”

Trump told reporters Friday that the talks will continue through the weekend.

While Trump claimed there aren’t “too many significant differences” remaining, he said the United States would continue the blockade until negotiations are finalized and formalized.

“When the agreement is signed, the blockade ends,” the president told reporters in Phoenix.

Times staff writer Ana Ceballos contributed to this report.

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Read the Supreme Court’s Shadow Papers

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Read the Supreme Court’s Shadow Papers

CHAMBERS OF

JUSTICE ELENA KAGAN

Supreme Court of the United States Washington, D. C. 20343

February 7, 2016

Memorandum to the Conference

Re: 15A773 West Virginia, et al. v. EPA, et al.
15A776 Basin Elec. Power Cooperative, et al. v. EPA, et al. 15A787 Chamber of Commerce, et al. v. EPA, et al.
15A778 Murray Energy Corp., et al. v. EPA, et al.

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15A793 North Dakota v. EPA, et al.

I agree with Steve that we should direct the States to seek an extension from the EPA before asking this Court to intervene. We could also include, at the end of such an order, language along the lines of the following, to encourage the D. C. Circuit to act expeditiously in its resolution of this matter: “In light of that court’s agreement to consider this case on an expedited schedule, we are confident that it will [or even: we urge it to] render a decision with appropriate dispatch.” See Doe v. Gonzales, 546 U. S. 1301, 1308 (2005) (GINSBURG, J., in chambers); Kemp v. Smith, 463 U. S. 1344, 1345 (1983) (Powell, J., in chambers); Holtzman v. Schlesinger, 414 U. S. 1304, 1305, n. 2 (1973) (Marshall, J., in chambers).

The unique nature of the relief sought in these applications gives me real pause. The applicants ask us to enjoin a regulation pending initial review in the court of appeals. As we often say, “we are a court of review, not of first view.” See Cutter v. Wilkinson, 544 U. S. 709, 718 n. 7 (2005); cf. Doe, 546 U. S., at 1308 (“Re- spect for the assessment of the Court of Appeals is especially warranted when that court is proceeding to adjudication on the merits with due expedition.”). As far as I can tell, it would be unprecedented for us to second-guess the D. C. Circuit’s deci sion that a stay is not warranted, without the benefit of full briefing or a prior judi- cial decision.

On the merits, this is a difficult case involving a complex statutory and regu- latory regime. Although the parties’ abbreviated discussion of the issues at stake here makes it difficult for me to determine with any confidence which side is likely to ultimately prevail, it seems to me that at this stage the government has the bet- ter of the arguments. The Chief’s memo focuses on the applicants’ argument that the “best system of emission reduction” refers “solely [to] installation of control technologies (e.g., scrubbers).” 2/5 Memo, at 2. The ordinary meaning of “system” is in fact quite broad, appearing to encompass what EPA has done here. Of course, we would want to consider this term in the larger context of the Clean Air Act’s regula-

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