‘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.'"



Gabbard Calls Signal Chats a ‘Mistake’ as Trump Officials Face Grilling over Leaked Military Plan

(L-R) Director of the National Security Agency, Gen. Timothy Haugh; FBI Director, Kash Patel; Director of National Intelligence, Tulsi Gabbard; CIA Director, John Ratcliffe; and Director of the Defense Intelligence Agency, Lt. Gen. Jeffrey Kruse testify before a House Permanent Select Committee on Intelligence hearing on "Worldwide Threats," on Capitol Hill in Washington, DC, on March 26, 2025. (AFP)
(L-R) Director of the National Security Agency, Gen. Timothy Haugh; FBI Director, Kash Patel; Director of National Intelligence, Tulsi Gabbard; CIA Director, John Ratcliffe; and Director of the Defense Intelligence Agency, Lt. Gen. Jeffrey Kruse testify before a House Permanent Select Committee on Intelligence hearing on "Worldwide Threats," on Capitol Hill in Washington, DC, on March 26, 2025. (AFP)
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Gabbard Calls Signal Chats a ‘Mistake’ as Trump Officials Face Grilling over Leaked Military Plan

(L-R) Director of the National Security Agency, Gen. Timothy Haugh; FBI Director, Kash Patel; Director of National Intelligence, Tulsi Gabbard; CIA Director, John Ratcliffe; and Director of the Defense Intelligence Agency, Lt. Gen. Jeffrey Kruse testify before a House Permanent Select Committee on Intelligence hearing on "Worldwide Threats," on Capitol Hill in Washington, DC, on March 26, 2025. (AFP)
(L-R) Director of the National Security Agency, Gen. Timothy Haugh; FBI Director, Kash Patel; Director of National Intelligence, Tulsi Gabbard; CIA Director, John Ratcliffe; and Director of the Defense Intelligence Agency, Lt. Gen. Jeffrey Kruse testify before a House Permanent Select Committee on Intelligence hearing on "Worldwide Threats," on Capitol Hill in Washington, DC, on March 26, 2025. (AFP)

Director of National Intelligence Tulsi Gabbard said Wednesday it was a "mistake" for national security officials to discuss sensitive military plans on a group text chain that also included a journalist — a leak that has roiled President Donald Trump's national security leadership.

Speaking before the House Intelligence Committee, Gabbard said the conversation included "candid and sensitive" information about military strikes against Houthi rebels in Yemen. But as she told senators during testimony on Tuesday, she said the texts did not contain any classified information.

"It was a mistake that a reporter was inadvertently added," Gabbard said.

Wednesday's hearing was called to discuss an updated report on national security threats facing the US Instead, much of the focus was on the text chain, which included Gabbard, CIA Director John Ratcliffe, Secretary of Defense Pete Hegseth, Vice President JD Vance and other top officials.

Jeffrey Goldberg, the editor-in-chief of The Atlantic, was also added, and on Wednesday his publication released more details from the chats, showing the level of detail they offered about the strikes.

Democrats have demanded an investigation into the sloppy communication, saying it may have exposed sensitive military information that could have jeopardized the mission or put US service members at risk.

The National Security Council has said it will investigate the matter, which Trump on Tuesday downplayed as a "glitch." Goldberg said he received the Signal invitation from Mike Waltz, Trump’s national security adviser, who was in the group chat and has taken responsibility for the lapse.

Even though the texts contained detailed information on military actions, Gabbard, Ratcliffe and the White House have all said none of the information was classified — an assertion Democrats flatly rejected on Wednesday.

"You all know that's a lie," Rep. Joaquin Castro, D-Texas, told Ratcliffe and Gabbard, who said that any decisions to classify or declassify military information falls to the secretary of defense.

Several Democrats on the panel said Hegseth should resign because of the leak.

"This is classified information. It’s a weapon system, as well as a sequence of strikes, as well as details of the operations," said Rep. Raja Krishnamoorthi, a Democrat from Illinois. "He needs to resign immediately."

Ratcliffe defended his use of Signal as "appropriate" and said questions over the Signal leak have overshadowed the military operation targeting the Houthis.

"What is most important is that the mission was a remarkable success," he told lawmakers. "That’s what did happen, not what possibly could have happened."

The discussion at times grew heated as Ratcliffe and Democratic lawmakers spoke over one another. At one point, Rep. Jimmy Gomez, an Illinois Democrat, asked whether he knew whether Hegseth was drinking alcohol when he participated in the chat.

"I think that’s an offensive line of questioning," Ratcliffe angrily replied. "The answer is no."

Ratcliffe and Gomez then began shouting over each other as Gomez sought to ask a follow-up question. "We want to know if his performance is compromised," Gomez said.

Wednesday's hearing was called to discuss the intelligence community's annual report on threats to American national security. The report lists China, Russia, Iran and North Korea as strategic adversaries, and notes that drug cartels and transnational criminal organizations pose other threats to Americans.

The presentations from top Trump appointees reflect Trump's foreign policy priorities, including a focus on combating the flow of fentanyl, illegal immigration and human trafficking, and are taking place as Trump attempts to work out a ceasefire between Russia and Ukraine three years after Russia's invasion.