How Trump chose Dan Caine to be top US military officer

The Rise of a Surprise pick: Dan Caine and His Path to the Top

Dan Caine, a retired Air Force three-star general, was not a name frequently mentioned in Washington circles before Friday night. However, President Donald Trump’s sudden announcement of Caine as his surprise pick to become the next Chairman of the Joint Chiefs of Staff (JCS) has brought him into the national spotlight. Trump first met Caine in 2018 during a visit to Iraq, where Caine was serving as the deputy commander of a special operations task force fighting the Islamic State. In a speech at the 2019 Conservative Political Action Conference, Trump recalled Caine’s bold assertion that the militant group could be destroyed in just one week. Since then, Trump has frequently retold this story, praising Caine as a “real general, not a television general.” Caine’s nomination has sent shockwaves through the military and political establishment, as it comes on the heels of Trump’s unexpected firing of the outgoing JCS Chairman, Air Force General C.Q. Brown.

A Career Marked by Service and Entrepreneurship

Dan Caine’s military career is unconventional by the standards of previous JCS chairmen. Unlike many who have risen to the top, Caine did not lead a major combatant command or a military branch before his retirement. Trump has claimed that Caine was “passed over for promotion by Sleepy Joe Biden,” though Caine’s credentials are undeniably impressive. A retired F-16 pilot, Caine accumulated over 2,800 flight hours during his career. He also played a critical role in defending Washington, D.C., on September 11, 2001, when he was part of the team tasked with protecting the nation’s capital from hijacked aircraft. Caine has described the weight of responsibility he felt that day, knowing that a mistake could have catastrophic consequences.

Caine’s post-military career has been just as unconventional. He joined a venture capital firm, Shield Capital, last month and has also been associated with two other investment firms. His LinkedIn profile reflects a man who has seamlessly transitioned from military service to the private sector. Before his retirement late last year, Caine served as the associate director for military affairs at the Central Intelligence Agency (CIA). His diverse experience, ranging from combat operations to counterterrorism policy and investment, sets him apart from traditional candidates for the JCS role.

An Unconventional Path to the Top

Caine’s nomination to become the Chairman of the Joint Chiefs of Staff breaks with tradition in more ways than one. Most generals who have held the position have led major combatant commands or served as the heads of military branches. Caine, however, rose to prominence through his work in special operations and counterterrorism. His time in Iraq from 2018 to 2019, where he worked alongside Trump, appears to have been a turning point. Trump has repeatedly praised Caine’s no-nonsense approach and his willingness to challenge conventional wisdom, qualities that may have endeared him to the president.

Caine’s career story is one of determination and adaptability. Growing up as the son of a fighter pilot, he always dreamed of following in his father’s footsteps. After graduating from the Virginia Military Institute in 1990 with a degree in economics, he went on to fly F-16s and later transitioned into roles that blended military service with policy and intelligence work. Despite being passed over for promotion during the Biden administration, Caine remained committed to public service, taking on roles that kept him engaged with national security issues.

A Legacy of Service and the Weight of Responsibility

Caine’s military service is a testament to his dedication to the nation. In addition to his combat roles, he held several key positions in Washington, D.C., including 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 association with the National Guard and his work as a “serial entrepreneur and investor” from 2009 to 2016 further highlight his diverse skill set.

Despite his impressive resume, Caine’s nomination has raised questions about his political neutrality. The military is constitutionally required to remain apolitical, and Caine’s close association with Trump has sparked concerns. However, a senior military official who worked with Caine for over a decade has vouched for his professionalism, stating that Caine “puts the mission and troops above politics.” Caine’s first concern upon learning of his nomination was reportedly the treatment of General Brown, whom Trump fired unexpectedly. This focus on respect and protocol may bode well for his ability to navigate the complexities of the JCS role.

Navigating the Political Landscape

The road ahead for Dan Caine will be challenging. If confirmed by the Senate, he will lead a military undergoing significant changes during the first 30 days of the Trump administration. The Joint Chiefs of Staff are still reeling from the abrupt firing of General Brown, and Caine will need to steady the ship while earning the trust of both the military and lawmakers. His ability to remain apolitical will be tested, particularly given Trump’s history of involving the military in partisan issues.

Caine’s greatest challenge may be balancing the demands of his new role with the political pressures emanating from the White House. While he has thus far avoided being drawn into political controversies, his association with Trump could complicate his tenure. The fact that he was present during a 2018 incident in which service members donned “Make America Great Again” hats in Trump’s presence has raised eyebrows. Trump has recounted this story with pride, noting that the troops disregarded protocols to express their support for him. Caine’s handling of such situations will be closely watched as he assumes the highest-ranking position in the military.

The Confirmation Process and the Road Ahead

Caine’s nomination sets the stage for what promises to be a contentious Senate confirmation process. Senators will scrutinize his military record, his post-retirement activities, and his ability to maintain the military’s independence from political influence. Caine’s entrepreneurial ventures, including his recent role at Shield Capital, will also likely come under scrutiny. While his background in counterterrorism and special operations may resonate with some lawmakers, others may question his readiness to lead the entire military.

If confirmed, Caine will be promoted to four-star general and will serve a four-year term as the nation’s most senior active-duty officer. His success in this role will depend on his ability to unite the military, navigate the political landscape, and maintain the trust of both Congress and the American people. While Trump’s enthusiasm for Caine is clear, the broader implications of this nomination for the military and the nation remain to be seen. As Caine prepares for the challenges ahead, his focus on “the mission and troops above politics” will be put to the ultimate test.