Recently, President Trump decided to replace General Charles Q. Brown Jr. as chairman of the Joint Chiefs of Staff. He had two potential candidates in mind.
The first candidate was General Michael E. Kurilla, a prominent Army general overseeing U.S. military operations in the Middle East. The second was Dan Caine, a lesser-known retired Air Force officer with a unique career that included being a fighter pilot, a CIA liaison, and even starting a regional airline. Trump and Caine had a meeting at the White House on February 14, during which Trump began to lean towards choosing him.
The following day, Trump announced on social media that he had selected General Caine. He praised Caine as “an accomplished pilot and national security expert” with extensive experience in special operations.
This decision reflects a significant shift happening at the Pentagon, as it involves careful discussions among a select group of senior officials, including Defense Secretary Pete Hegseth. Unlike his first term, when Trump seemed to favor military leaders, he grew frustrated with them, believing they lacked loyalty.
Trump’s choice of Caine over Kurilla stemmed partly from Caine’s minimal ties to the Biden administration and Trump’s impression from a brief encounter in Iraq, where Caine convincingly argued that the Islamic State could be defeated quicker than others suggested.
Throughout the years, Trump had praised Caine for his strong views on military strategy. Now, Caine will face numerous national security challenges, including the ongoing situation in Ukraine and the military threat from China. He will need to provide honest military advice to Trump, while also managing expectations about loyalty.
Trump has had a complicated relationship with generals. After his regret over appointing General Mark A. Milley, who he felt was not loyal, he became cautious about picking leaders who might challenge his authority.
General Brown, who is stepping down, made history as one of the few African Americans to hold this position. During the search for a new chairman, officials considered a few names before narrowing it down to Kurilla and Caine. While Kurilla was familiar to Trump and actively involved in military strategy discussions, he resembled the more senior officers Trump had become disillusioned with.
In contrast, Caine’s diverse career captured Trump’s attention. Caine had worked in various military and intelligence roles, including protecting Washington, D.C., on September 11, 2001. His offbeat path included founding a regional airline while serving in the Air National Guard. Recently, he worked closely with the CIA, focusing on technology and national security.
Caine first impressed Trump during a visit to Al Asad air base in Iraq. In a briefing, he indicated that the Islamic State could be defeated much faster than expected. Trump has repeated this encounter, embellishing details over time. However, some like John Bolton, who was with Trump that day, say the specifics differ from the president’s account.
Trump also appreciated Caine’s nickname, “Razin,” which aligns with the strong warrior image Trump prefers in his military leaders. In his announcement, Trump credited Caine with playing a vital role in the rapid defeat of the ISIS caliphate.
Interestingly, Trump saw Caine’s previous lack of promotion under Biden as a mark of distinction, suggesting he would not be beholden to the previous administration. Friends of Caine describe him as somewhat reserved, avoiding political discussions, which adds an air of mystery regarding his political affiliations.
As Caine returns to a leadership role, he faces an important challenge: will he provide honest military advice to Trump, or will he cater to what the president wants to hear? General Kenneth F. McKenzie Jr., who has worked with Caine, believes Caine is not a “yes-man” and stresses the importance of his ability to speak truthfully in the face of authority.
Senator Jack Reed plans to question Caine during his confirmation hearing about whether he can maintain that honest demeanor in his new role.
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