Trump’s Discontent with Military Leaders Led to an Unusual Selection

By the end of last week, President Trump had made the decision to dismiss Gen. Charles Q. Brown Jr., the chairman of the Joint Chiefs of Staff, and intended to choose one of two contrasting candidates, as reported by two officials from the administration.

One candidate was Gen. Michael E. Kurilla, an aggressive Army four-star general responsible for overseeing U.S. military operations in the Middle East, one of the most significant roles within the Pentagon.

The other was Dan Caine, a lesser-known retired three-star Air Force officer with a unique career trajectory that included his time as a fighter pilot, the primary military liaison to the C.I.A., and as an Air National Guard officer who co-founded a regional airline in Texas.

Mr. Trump and General Caine met for about an hour at the White House on February 14. The president largely reached his conclusion after a discussion with Defense Secretary Pete Hegseth the previous Thursday, according to aides.

The following evening, Mr. Trump took to social media to announce his selection of General Caine, describing him as “an accomplished pilot, national security expert, successful entrepreneur, and a ‘warfighter’ with extensive interagency and special operations experience.”

This decision, part of an unprecedented overhaul at the Pentagon, was the result of intense deliberations over two weeks among a select group of senior administration officials, including Mr. Hegseth, Vice President JD Vance, and national security adviser Michael Waltz. These officials spoke anonymously to discuss sensitive matters.

During his first term, Mr. Trump initially aimed to develop a close rapport with the top military leaders, often referring to them as “my generals.” However, this perspective shifted to frustration as he began to perceive them as disloyal.

This skepticism led the president to bypass more conventional candidates for General Brown’s replacement and select General Caine, who had been relatively obscure. According to those close to Mr. Trump’s reasoning, this decision was influenced partially by General Caine’s lack of association with the Biden administration and a brief encounter Mr. Trump had with him in Iraq six years prior, which convinced him that General Caine embodied the proactive spirit he values in military leaders.

In recent years, Mr. Trump has publicly commended General Caine for asserting during their Iraq visit that the Islamic State could be defeated much more swiftly than his senior advisors had indicated.

Their renewed association will be tested by national security issues like the conflict in Ukraine and escalating military threats from China, as well as whether General Caine can meet Mr. Trump’s expectations of loyalty while maintaining the politically neutral role of providing sound military advice to the commander in chief.

Since 2019, Mr. Trump has been fixated on the Joint Chiefs chairman position, having first appointed Gen. Mark A. Milley, General Brown’s predecessor—a decision that Mr. Trump later regretted.

He perceived General Milley as a showboater and traitor, especially after the general apologized for being photographed with Mr. Trump in Lafayette Square, following the clearance of peaceful protestors after George Floyd’s death in May 2020. Frustrated by Milley’s allegiance to the Constitution rather than to him, their relationship soured.

“Trump appreciates his generals until that appreciation fades,” John R. Bolton, Mr. Trump’s national security adviser during his first term, remarked in an interview.

After Mr. Trump’s election for a second term, it quickly became apparent that he would seek to replace General Brown, a decorated F-16 fighter pilot who, in October 2023, became only the second African American to chair the Joint Chiefs.

Following Mr. Hegseth’s narrow confirmation as defense secretary last month, the likelihood of this replacement turned near inevitable, according to administration officials. Mr. Hegseth had previously claimed that General Brown should be dismissed over what he termed a “woke” emphasis on diversity, equity, and inclusion in the military. He also cast doubt on whether the general’s promotion was due to merit or race, given his four decades of service.

Several weeks ago, the process for selecting a new chairman began in earnest, according to officials. Adm. Samuel J. Paparo Jr., who heads U.S. forces in the Indo-Pacific, was briefly considered alongside various other candidates.

However, the field quickly narrowed down to General Kurilla and General Caine.

On paper, General Kurilla appeared to have the advantage, as he was regularly meeting with Mr. Trump and other senior national security officials to discuss military priorities in the Middle East. Furthermore, General Kurilla was anticipating the conclusion of his tenure at Central Command in the coming months and had expressed interest in the position, as shared by several current and former military officials.

Conversely, General Caine had just retired after completing his last assignment as the Pentagon’s liaison to the C.I.A., and subsequently joined Shield Capital, a California-based firm specializing in cybersecurity and artificial intelligence.

At 56, General Caine, a graduate of the Virginia Military Institute in 1990 with a degree in economics, followed in his father’s footsteps as an F-16 pilot and took on the role of the lead aviator tasked with protecting Washington on September 11, 2001, following the terrorist attacks on the Pentagon and the World Trade Center.

His post-9/11 career took on an unusual path, as he translated each opportunity into further professional achievements. He served as a White House fellow at the Agriculture Department and as a counterterrorism expert on the Homeland Security Council under President George W. Bush, alongside various secretive intelligence and special operations missions, both domestically and internationally.

Additionally, while serving as a part-time Air National Guard officer, General Caine co-founded RISE Air, a regional airline, and managed other private businesses, as per his LinkedIn profile and conversations with acquaintances and former colleagues.

However, what caught Mr. Trump’s attention was a brief visit he made to Al Asad Air Base in Iraq in December 2018, where General Caine relayed to the president that the Islamic State could be swiftly defeated, contrary to the two-year timeline posited by senior advisors—an assertion Mr. Trump has cited frequently since.

At a Conservative Political Action Conference meeting last year, Mr. Trump even shared that General Caine donned a Make America Great Again hat during their meeting in Iraq.

Details of these accounts have evolved over time with Mr. Trump’s retellings. However, Mr. Bolton, who was present on the trip to Iraq, stated that General Caine and another senior general had informed the president about plans to defeat the remaining ISIS forces in two to four weeks, not one week. Mr. Bolton firmly denied that General Caine ever wore a MAGA hat, saying, “No way.”

In his social media post, Mr. Trump also highlighted General Caine’s nickname, “Razin,” noting his fascination with former Defense Secretary Jim Mattis’s moniker, “Mad Dog,” which Mr. Mattis detested.

General Caine’s nickname represented the type of combative warrior that matched Mr. Trump’s ideal perception of a top general, according to officials.

In his post on Friday, Mr. Trump reiterated his admiration for General Caine’s counterterrorism capabilities. “During my first term, Razin was crucial in the total destruction of the ISIS caliphate,” the president remarked. “It was accomplished in record time—just weeks. Many so-called military ‘geniuses’ predicted it would take years to eradicate ISIS. General Caine, however, asserted it could be done quickly, and he delivered.”

Mr. Trump also disclosed another reason behind his unconventional choice, stating that General Caine had been overlooked for a promotion by President Joseph R. Biden Jr., a claim Biden officials said they could not address. To Mr. Trump, this perceived oversight signified General Caine’s lack of allegiance to the previous administration, aligning with Trump’s view that many senior officers are inept and overly politically correct, further suggesting that General Caine possesses a different mindset.

Friends and former colleagues note that General Caine, while intensely focused and humble, has been uneasy with Mr. Trump’s portrayal of his role in the defeat of the Islamic State. General Caine did not respond to requests for comment on Sunday.

Nevertheless, when the White House reached out a couple of weeks ago as he was preparing to relocate to Dallas, friends of General Caine mentioned that he promptly accepted the meetings with Mr. Trump and senior aides, ultimately taking the position out of a sense of duty to his country.

This leads to a critical question for General Caine as he gears up to return to active duty shortly and prepare for what promises to be a challenging Senate confirmation hearing: Will he provide his most candid military advice to Mr. Trump, or will he opt to tell the president what he wishes to hear?

“He has always been straightforward and candid in interagency interactions, which is no easy task,” Gen. Kenneth F. McKenzie Jr., a former Central Command head who frequently collaborated with General Caine during his time at the C.I.A., commented on Sunday. “I never perceived him as a yes-man.”

Senator Jack Reed of Rhode Island, the senior Democrat on the Armed Services Committee, stated in an interview on Sunday that he would focus on that key issue during General Caine’s hearing: “Will he possess the capability to speak truth to power?”

Jonathan Swan, Maggie Haberman and Helene Cooper contributed reporting.