As President Donald Trump and his top advisors weighed a military strike against Iran in early June, Vice President JD Vance and Secretary of State Marco Rubio wanted assurances that the US military wouldn't get bogged down in another Middle Eastern conflict.

General Dan Caine at a Pentagon press conference on 26/6. Photo: AP

General Dan Caine at a Pentagon press conference on 26/6. Photo: AP

Newly confirmed Chairman of the Joint Chiefs of Staff, General Dan Caine, shared similar concerns about putting American troops in harm's way. He spread a map inside the White House Situation Room, explaining how the Pentagon could protect pilots and other US forces in the Middle East from any retaliation should they be ordered to strike Iranian nuclear facilities.

Caine's confident assertions impressed President Trump. And when the June 21st strike on three Iranian nuclear sites unfolded almost exactly as he had outlined, his influence with the President was cemented.

Within a week of the operation, Caine had made two public appearances, earning effusive praise from the President. "I have to say, General 'Razin' Caine has been incredible", Trump told reporters on 25/6, using Caine's Air Force call sign, signaling a close rapport between the two men.

According to several US military officials familiar with the matter, in his short time in the position, Caine has become one of President Trump's closest advisors. In the week before and immediately after the attack, he was at the White House almost daily. During the evening of the 21st, as the strike unfolded, President Trump repeatedly turned to Caine for answers inside the Situation Room. Caine narrated the attack, pointing out details on maps and explaining what was happening in real-time. He stated his belief that Iran was caught completely off guard and fielded more questions than any other official in the room.

A senior US official stated that President Trump consistently sought out Caine for ground-truth information on what was happening. "General Caine is detail-oriented and laser-focused on executing President Trump's military objectives", Vice President Vance told the Wall Street Journal. "In roughly two months on the job, General Caine has helped oversee a series of incredibly precise air strikes, resulting in zero US casualties and the obliteration of Iran's nuclear capabilities. I think the best way to judge his effectiveness is by the results. America is safer and stronger thanks to the successful operation he oversaw last week."

Before becoming a trusted general by President Trump's side, Caine was relatively unknown. His ascent began at an air base in western Iraq in 2018. Caine, then deputy commander of the special operations task force for Operation Inherent Resolve against the Islamic State (IS), briefed President Trump at the base.

"The President was taken with Caine", a former senior military officer with knowledge of the meeting said. "He clearly liked the way he communicated, his direct approach in answering questions."

At a 2024 fundraiser for major donors, Trump recounted the meeting with Caine. According to Trump, other military leaders in his first term had told him the US couldn't defeat IS quickly, but Caine asserted they "could crush them".

Caine spent much of his military career as an F-16 pilot in the Air National Guard, deploying multiple times to the Middle East. He flew combat air patrols over Washington after the 9/11 attacks. Later, he worked on special operations tactics for stealth aircraft and highly classified programs at the Pentagon, Joint Special Operations Command, and the Central Intelligence Agency (CIA).

General Caine with President Trump and other senior administration officials in the White House Situation Room during the Iran strike. Photo: The White House

General Caine with President Trump and other senior administration officials in the White House Situation Room during the Iran strike. Photo: The White House

After returning from his Iraq deployment, he retired from the Air Force in 2024 as a two-star general, just months before Trump began his second term. White House Chief of Staff Susie Wiles subsequently met with Caine to discuss a potential role in the Trump administration. Ultimately, he was brought back into the military and nominated to be Chairman of the Joint Chiefs.

In an April vote, the Senate confirmed Caine to the position by a vote of 60 to 25. Caine became the first retired military officer and the first general not holding a 4-star rank to serve as the Pentagon's top military officer.

Even before taking the job, Caine had to deflect accusations that he was too close to President Trump. During his Senate confirmation hearing, he denied a story Trump had told about their 2018 meeting. According to Trump, when the two met, Caine wore a MAGA hat and said: "I’m willing to kill for you". However, before the committee, Caine said he believed the President may have been talking about someone else. "I have never worn any items with political messaging nor said anything of that nature", he stated. John Bolton, Trump's national security advisor from 2018 to 2019, said he never saw Caine wearing a MAGA hat or saying anything political during the 2018 Iraq trip.

"My impression was that Caine would be a typical apolitical general that we always try to get for the Chairman of the Joint Chiefs of Staff", Bolton said.

As President Trump and his team debated the Iran strike plan in the Situation Room, Caine laid out military options rather than advocating for a specific course of action. During the week leading up to the strike, Caine was at the White House daily, helping the administration plan operational security procedures and how to maintain secrecy. He returned to the White House on 22/6 for meetings after the strike was complete.

Before that, according to some White House aides, Caine wasn't a regular presence. They also knew little of his background or life outside of the government.

A White House official said President Trump warmed to Caine because he was concise and answered questions quickly without embellishment. "He never beats around the bush and gets right to the point", the official said.

Caine details the Iran strike during a Pentagon press conference on 26/6. Photo: AP

Caine details the Iran strike during a Pentagon press conference on 26/6. Photo: AP

At a Pentagon news conference hours after the Iran strike, Defense Secretary Hegseth praised President Trump for conducting a "bold and brilliant operation" and declared Iran’s nuclear ambitions were "obliterated". Caine, in his blue Air Force uniform, recounted the details of the operation and offered a more cautious assessment of its success. He said the Iranian sites "suffered extremely heavy damage and destruction" but noted it would take time for a final assessment. He made no mention of President Trump.

Vu Hoang (According to WSJ, AFP, Reuters)