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‘He’s a Real General’: How Trump Chose Dan Caine to Be Top US Military Officer

This image provided by the US Air Force shows Lt. Gen. Dan Caine. (US Air Force via AP)
This image provided by the US Air Force shows Lt. Gen. Dan Caine. (US Air Force via AP)
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‘He’s a Real General’: How Trump Chose Dan Caine to Be Top US Military Officer

This image provided by the US Air Force shows Lt. Gen. Dan Caine. (US Air Force via AP)
This image provided by the US Air Force shows Lt. Gen. Dan Caine. (US Air Force via AP)

Dan Caine may not have been on Washington's radar before Friday night. But President Donald Trump's fascination with the retired three-star general, his surprise pick to become the next chairman of the Joint Chiefs of Staff, appears to go back to their first meeting in Iraq in 2018.

Caine, then the deputy commander of a special operations task force fighting ISIS, told the president that the extremist group could be destroyed in just a week, Trump recalled during a speech to the Conservative Political Action Conference in 2019.

Since then, he has retold the story about how he met "Razin" Caine multiple times - and the praise has only grown more effusive.

"He's a real general, not a television general," Trump said in Miami on Wednesday, two days before his Truth Social post catapulted Caine from retirement to a nomination to be the most senior active-duty officer in the US military.

If approved by the Senate, Caine will take over a military that is reeling from change in the first 30 days of the Trump administration and will inherit a Joint Staff rattled by Trump's surprise firing of the chairman of the Joint Chiefs of Staff, Air Force General C.Q. Brown.

Caine, a retired F-16 pilot, will be promoted to four-star general, and then have to undergo a potentially grueling Senate confirmation process to get a four-year term as the uniformed head of the nation's military.

UNCONVENTIONAL PICK

Caine's military career is a far cry from the traditional path to becoming the president's top military adviser. Previous generals and admirals have led a combatant command or a military branch of service.

Caine did not rise that high in the ranks before retirement. According to Trump, he was "passed over for promotion by Sleepy Joe Biden," whom Trump defeated in November's presidential campaign.

"But not anymore!", Trump wrote on Truth Social.

Earlier this year Caine described on a podcast how as a young man he wanted to follow in the footsteps of his father, a fighter pilot.

"We started moving around as a kid. So I felt like this was something that I really, really, really wanted to do, was fly jets in the Air Force," Caine said.

He graduated in 1990 from the Virginia Military Institute with a bachelor's degree in Arts and Economics.

Caine, who flew more than 2,800 hours in the F-16, was one of the pilots tasked with protecting Washington on September 11, 2001, when al-Qaeda hijackers slammed commercial jets into the Pentagon and the World Trade Center in New York City.

Caine realized he might have to shoot down a hijacked plane if one crossed his path.

"I was very mindful that if we made a mistake or if we got it wrong or if we missed somebody and we did not shoot, the consequences of that could be catastrophic," Caine, who has also flown the T-37 and T-38 aircraft, said in an article posted on the CIA website.

Caine held a number of posts in the capital from 2005. He was as a special assistant to the secretary at the Department of Agriculture and then policy director for counterterrorism at the White House's homeland security council.

According to his official Air Force biography, Caine was a part-time member of the National Guard and "a serial entrepreneur and investor" from 2009 to 2016.

He was most recently the associate director for military affairs at the Central Intelligence Agency, before his retirement late last year.

But it was his time in Iraq from 2018 to 2019 that helped him gain Trump's attention.

Caine will be under particular scrutiny to ensure that he is apolitical, a concern that was heightened by the Friday night firing of Brown, a four-star general. Uniformed military officials are supposed to be loyal to the US Constitution and independent of any party or political movement.

A senior US military official who has worked with Caine for more than a decade said he would seek to keep the military out of politics.

Caine "puts the mission and troops above politics. He is not a political guy," the official said.

How far Caine can keep the military out of politics may largely depend on Trump - who in the past has dragged the military into partisan issues.

In a recent re-telling of their first meeting in Iraq, Trump said that Caine was in the hangar where service members started putting on "Make America Great Again" hats.

"They all put on the Make America Great Again hat. Not supposed to do it," Trump said during a speech last year.

"I said, 'you're not supposed to do that. You know that.' They said, 'It's OK, sir. We don't care.'"

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North Korea Says It Has Repaired Its Damaged Second Destroyer, a Claim Met with Outside Skepticism 

A photo released by the official North Korean Central News Agency (KCNA) shows North Korean leader Kim Jong Un (Center-R) and his daughter Kim Ju Ae (Center-L) attending the launch ceremony of a destroyer named Kang Kon at the Rajin shipyard in Rason, North Korea, 12 June 2025 (issued 13 June 2025). (EPA)
A photo released by the official North Korean Central News Agency (KCNA) shows North Korean leader Kim Jong Un (Center-R) and his daughter Kim Ju Ae (Center-L) attending the launch ceremony of a destroyer named Kang Kon at the Rajin shipyard in Rason, North Korea, 12 June 2025 (issued 13 June 2025). (EPA)
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North Korea Says It Has Repaired Its Damaged Second Destroyer, a Claim Met with Outside Skepticism 

A photo released by the official North Korean Central News Agency (KCNA) shows North Korean leader Kim Jong Un (Center-R) and his daughter Kim Ju Ae (Center-L) attending the launch ceremony of a destroyer named Kang Kon at the Rajin shipyard in Rason, North Korea, 12 June 2025 (issued 13 June 2025). (EPA)
A photo released by the official North Korean Central News Agency (KCNA) shows North Korean leader Kim Jong Un (Center-R) and his daughter Kim Ju Ae (Center-L) attending the launch ceremony of a destroyer named Kang Kon at the Rajin shipyard in Rason, North Korea, 12 June 2025 (issued 13 June 2025). (EPA)

North Korea said Friday it has repaired its damaged second naval destroyer and launched it into the water in the presence of leader Kim Jong Un, about three weeks after it capsized during an earlier, botched launch ceremony.

The North’s Korean Central News Agency said Friday it launched the destroyer — the second it built this year — off its east coast Thursday.

The country's extremely secretive nature makes it virtually impossible to independently confirm its announcement on the ship’s repair. Outside observers doubt whether the ship’s engine, weapons systems and other electronic equipment can function normally, as parts of the warship were submerged for about two weeks.

North Korea's failed launch on May 21 sparked fury from Kim, who has vowed to build a stronger navy to cope with what he calls escalating US-led threats against his country. Kim said the incident was caused by criminal negligence and ordered officials to repair the warship before a ruling Workers’ Party meeting in late June. North Korean authorities later detained four officials, including the vice director of the Workers’ Party’s munitions industry department over the botched launch.

In a launch ceremony, Kim said the country’s two destroyers will play a big role in improving the North Korean navy’s operational capabilities, according to KCNA.

Kim reiterated previous claims that his naval buildup is a justified response to perceived threats posed by the US and South Korea, which in recent years have expanded their combined military exercises and updated their deterrence strategies to counter Kim’s advancing nuclear program. He said the North will respond to such external threats with “overwhelming military action.”

“It will not be long before the enemy nations themselves experience just how provoking and unpleasant it is to sit back and watch as our warships freely move near the edges of their sovereign waters,” Kim said.

During his speech, Kim said a North Korean shipyard worker died during the repairs and offered his “deepest condolences” to his family, including his wife and son who were present at the launch event.

Outside experts earlier said it remained unclear how severely the 5,000-ton-class destroyer was damaged and questioned North Korea's claim that it needed 10 days to pump out the seawater, set the ship upright and fix its damages that it described as “not serious.”

Previous satellite photos showed the North Korean destroyer lying on its side at the northeastern port of Chongjin, with its stern partly under water. Last week, North Korea said it had righted the warship and would move it to the Rajin port, which is further north of Chongjin and close to the border with Russia, for the next stage of its restoration works.

“Considering the time they needed to raise the vessel, they would have had less than two weeks to carry out the real repair work,” said Yang Uk, an analyst at Seoul’s Asan Institute for Policy Studies. “Would that have been enough time to completely fix everything and bring the vessel to a state where it’s operationally capable? I think that’s highly unlikely.”

Lee Illwoo, an expert with the Korea Defense Network in South Korea, said what was likely flooded in the North Korean ship were its engine room, missile launch tubes and anti-air weapons systems, which all involve electronic systems that are highly vulnerable to damages if exposed to seawater.

Lee said the ship's move to Rajin implies Russian experts have likely been assisting North Korea with repairs.

Military cooperation between North Korea and Russia has been flourishing significantly in recent years, with the North supplying troops and ammunitions to support Russia's war against Ukraine.

Kim wants a bigger navy

The damaged warship was in the same class as the country’s first destroyer unveiled in April, which experts assessed as the North’s largest and most advanced warship to date. Experts say the North's two destroyers were both likely built with Russian help.

Kim said the ruling Workers’ Party has confirmed plans to build two more 5,000-ton-class destroyers next year, according to Friday's KCNA dispatch.

Satellite imagery indicated North Korea had attempted to launch the second destroyer sideways, a method it had never used for warships. Many observers said it would be more difficult to maintain the balance of a big warship because it carries heavy weapons systems. But they said North Korea won't likely repeat the same mistake when it launches its third and fourth destroyers.

According to North Korea's timetable, its first two destroyers are to be deployed next year.

Despite its growing nuclear arsenal and huge 1.2 million-member standing army, North Korea's naval and aerial forces have been considered inferior to those of South Korea's. But North Korea's planned deployment of a series of 5,000-ton-class destroyers would pose “really a serious threat” to South Korea, whose navy hasn't still prepared itself to deal with such big, advanced enemy warships, according to Lee, the expert.

Earlier this week, the new liberal South Korean government led by President Lee Jae-myung halted frontline propaganda broadcasts as its first concrete step toward easing tensions between the rivals. North Korea hasn't responded formally to the measure.