Dan Caine may not have been a prominent figure in Washington prior to Friday night. However, President Donald Trump‘s interest in the retired three-star general, his unexpected choice for the next chairman of the Joint Chiefs of Staff, seems to trace back to their initial encounter in Iraq in 2018. At that time, Caine was serving as the deputy commander of a special operations task force engaged in the fight against the Islamic State. During a speech at the Conservative Political Action Conference in 2019, Trump recounted how Caine confidently asserted that the militant group could be defeated within a week.

Since that meeting, Trump has frequently shared the story of his interaction with “Razin” Caine, and his admiration for the general has only intensified. “He’s a real general, not a television general,” Trump remarked in Miami on Wednesday, just two days before his Truth Social announcement propelled Caine from retirement to a nomination for the highest active-duty position in the U.S. military. If the Senate confirms his appointment, Caine will assume command of a military facing significant changes in the early days of the Trump administration, following the unexpected dismissal of the previous chairman of the Joint Chiefs of Staff, Air Force General C.Q. Brown.

Caine, a retired F-16 pilot, is set to be promoted to four-star general and will then face a potentially challenging Senate confirmation process to secure a four-year term as the uniformed leader of the nation’s armed forces.

UNCONVENTIONAL CHOICE

Caine’s military trajectory diverges from the conventional route typically taken by those who become the president’s principal military advisor. Unlike previous generals and admirals who have led combatant commands or military branches, Caine did not reach such high ranks before his retirement. According to Trump, he was “passed over for promotion by Sleepy Joe Biden,” whom Trump defeated in the presidential election last November.

Trump expressed on Truth Social, “But that is no longer the case!” Earlier this year, Caine recounted on a podcast his aspiration to emulate his father, a fighter pilot, during his youth. “As a child, we moved frequently, which instilled in me a strong desire to fly jets in the Air Force,” Caine shared. He earned a bachelor’s degree in Arts and Economics from the Virginia Military Institute in 1990.

Having logged over 2,800 hours in the F-16, Caine was among the pilots assigned to safeguard Washington on September 11, 2001, when al Qaeda operatives hijacked commercial aircraft and targeted the Pentagon and the World Trade Center in New York City. He understood the gravity of potentially needing to intercept a hijacked plane. “I was acutely aware that a mistake on our part, or failing to act when necessary, could lead to catastrophic outcomes,” Caine, who has also piloted the T-37 and T-38, stated in an article featured on the CIA website.

From 2005 onward, Caine held various positions in the capital, serving as a special assistant to the secretary at the Department of Agriculture and later as the policy director for counterterrorism at the White House’s Homeland Security Council. His official Air Force biography notes that he was a part-time member of the National Guard and “a serial entrepreneur and investor” from 2009 to 2016. Most recently, he served as the associate director for military affairs at the Central Intelligence Agency before retiring late last year.

Caine’s tenure in Iraq from 2018 to 2019 was pivotal in attracting Trump’s attention. He will face heightened scrutiny to maintain an apolitical stance, especially following the recent dismissal of Brown, a four-star general.

Military officials in uniform are expected to uphold loyalty to the U.S. Constitution, remaining independent of any political affiliations or movements. A senior U.S. military official, who has collaborated with Caine for over a decade, emphasized his commitment to keeping the military separate from political matters. According to this official, Caine prioritizes the mission and the troops over political considerations, asserting that he is not politically inclined.

However, Caine’s ability to maintain this separation may largely hinge on Trump, who has previously involved the military in partisan debates. In a recent recounting of their initial encounter in Iraq, Trump noted that Caine was present when service members began donning “Make America Great Again” hats.

Trump recounted, “They all put on the Make America Great Again hat. Not supposed to do it,” during a speech last year, adding, “I said, ‘you’re not supposed to do that. You know that.’ They replied, ‘It’s OK, sir. We don’t care.'”