Will Dan Caine, Trump’s Joint Chiefs Chairman Pick, Be Candid or Reserved?

General Dan Caine: A Potential New Leader for the Joint Chiefs of Staff

Lt. Gen. Dan Caine’s dedication to the U.S. Constitution is symbolized by his well-worn pocket-sized copy, which he consistently carries with him, including during his time as a fighter pilot in the Air Force. This small book accompanied him on September 11, 2001, when he served as the lead aviator tasked with defending Washington D.C. in the wake of the devastating attacks on the Pentagon and the World Trade Center.

As the Senate Armed Services Committee prepares to evaluate General Caine’s nomination for the prestigious position of chairman of the Joint Chiefs of Staff—the highest military role in the nation—it is his unwavering commitment to the Constitution and his respected ethical standards that are likely to earn him a supportive reception at the hearing.

Colleagues and acquaintances have described General Caine as a modest and thoughtful officer who values integrity, distinguishing him from other senior officials who may prioritize loyalty to the president above all else. Raj Shah, a leader in a prominent Defense Department innovation unit and a long-time associate of Caine, praised him for his strong moral character, humility, and strategic insight.

However, the confirmation process won’t be without its challenges. General Caine is expected to face tough inquiries regarding his ability to provide candid military advice to President Trump. Senator Jack Reed of Rhode Island, the senior Democrat on the committee, emphasized the importance of assessing whether Caine could resist the pressure to align with the president’s desires, particularly if his guidance would compromise legal or ethical standards.

General Caine’s upcoming hearing will be a balancing act for him as he seeks to establish credibility with President Trump while adhering to the ethical norms of military conduct. This hearing arrives amidst significant scrutiny of the Trump administration’s handling of sensitive military operations, including an incident involving the careless distribution of classified information regarding military strikes in Yemen. Experts have raised alarms about potential risks to American pilots due to this lax information management.

The controversy surrounding Defense Secretary Pete Hegseth’s alleged disclosure of sensitive military details via the messaging app Signal has also garnered intense scrutiny, with the president downplaying the issue. Caine is likely to be asked pointed questions about these incidents, including whether he considers the shared information classified and whether he would have advocated for using secure government communications instead.

Despite the looming inquiries, it is probable that the committee members will approach their questions carefully, mindful of the potential implications of pushing Caine into a position where he might openly criticize the administration’s actions. The senators may view him as a necessary safeguard against potentially reckless military decisions made by the Trump administration, aiming to cultivate his influence right from the onset of his potential tenure.

At 56 years old and stepping out of military retirement, Caine faces a steep learning curve. While he has an impressive background as an F-16 pilot with combat experience and a history in intelligence and special operations, he lacks the command experience typically required by law for the position of chairman. However, President Trump has chosen to invoke a waiver to bypass this requirement.

Caine’s writings and public statements provide additional insight into his character. He frequently discusses the importance of communication, self-control, and honoring fallen service members on his blogs. Books like "The Daily Stoic," which extol virtues such as self-mastery and wisdom, resonate with his personal philosophy. His disciplined daily routine—including early morning reflection, rigorous workouts, and long work hours—speaks to his commitment to personal and professional growth.

While generally avoiding direct political discussions, Caine has touched on relevant issues in his writings. He once noted the implications of proposed tariffs during Trump’s administration, indicating his interest in broader economic discussions without taking a firm political stance.

Caine’s professional interactions with President Trump also hint at a complex relationship. They met once, during Trump’s visit to U.S. troops in Iraq, where Caine reportedly told the president that the defeat of the Islamic State could be achieved much quicker than previous estimates suggested. Trump’s recounting of this meeting painted a politically tinged picture, though Caine himself has maintained that he has never donned a MAGA hat, contrary to Trump’s assertions.

In the years following his military retirement, General Caine has ventured into the private sector, founding several companies and serving as a venture partner for investment firms. His background, including a history of establishing aviation-related businesses and consultancy roles, offers a contrast to prior military nominees who have followed more traditional paths.

Despite his extensive experience, Caine’s business ventures did not lead to substantial personal wealth, and he has reportedly turned down other military positions to focus on private sector opportunities. Friends and former colleagues describe him as a trustworthy, straightforward leader who acknowledges his fallibilities and actively listens to others—a quality that could serve him well in the complex landscape of military leadership.

As General Caine’s nomination moves forward, his commitment to ethical standards and integrity will be in the spotlight, setting the stage for what could be a significant chapter in U.S. military leadership.