Dan Caine

• 1. Introduction

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  John Daniel "Razin" Caine is an American general, born in 1968, who became chairman of the Joint Chiefs of Staff in 2025. His appointment broke three precedents at once. No earlier chairman had reached the job without first holding four-star rank. None had been nominated while retired from the military. None had been nominated as a member of a reserve component. Caine is also a venture capitalist and a former F-16 fighter pilot. How does a pilot who began in the Air National Guard end up advising a president on war? What did he do in the decades before Washington reached for him? And how did he handle the decisions that followed once he held the job?

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• 2. Fighter Pilot Years

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  John Daniel Caine was born in Elmira, New York, on the 10th of August 1968. His father, Steve Caine, was a fighter pilot who retired from the US Air Force as a lieutenant colonel. Caine graduated from Hahn American High School in Hahn, in the Rhineland-Palatinate region of Germany. In 1990 he earned a bachelor of arts in economics at the Virginia Military Institute, where he played soccer for the Keydets. In 2005 he added a master of arts in air warfare from American Military University.

  In October 1990 Caine was commissioned as a second lieutenant through the institute's Air Force Reserve Officer Training Corps. He entered the Euro-NATO Joint Jet Pilot Training Program at Sheppard Air Force Base in Texas and finished as a distinguished graduate in December 1993. The timing was uncomfortable. The Air Force was shrinking, and he worried that he might be given a job on the ground. His answer was to apply to a large number of Air National Guard units. He was selected as an F-16 pilot with the 138th Fighter Squadron at the Syracuse New York Air National Guard Base. He held that assignment from January 1994 to July 1998 and served at different times as the squadron's chief of training and chief of weapons.

  In 1998 Caine completed the Squadron Officer School by correspondence. From July 1998 to January 1999 he was an F-16 instructor pilot and chief of weapons for the 121st Fighter Squadron at Andrews Air Force Base in Maryland. He then went to the USAF Weapons School at Nellis Air Force Base in Nevada. He graduated from its Instructor Course in June 1999 as an outstanding graduate and returned to the 121st.

  After the September 11 attacks, Caine was among the pilots who patrolled the airspace over Washington, D.C. He held the post of chief of weapons and tactics for the squadron at the time. From November 2001 to February 2002 he was chief of group weapons and tactics for the 332nd Air Expeditionary Wing in Kuwait. Until January 2003 he was a counter-SCUD project officer for US Central Command at MacDill Air Force Base in Florida. During the 2003 invasion of Iraq, he developed a plan to counter the Scud missiles Iraqi forces possessed.

  Until May 2003 Caine was chief of weapons and tactics for the 410th Air Expeditionary Wing. He then became head of operations at the Test Center at the Tucson Air National Guard Base in Arizona, a post he held until August 2005. In 2004 he completed the Air Command and Staff College by correspondence. By 2005 his path was turning toward the White House.

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• 3. Washington and Special Operations

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  In 2005 Caine joined the White House Fellows program. From 2005 to 2006 he served as a special assistant to the United States Secretary of Agriculture, where he worked on the response to Hurricane Katrina. From October 2006 to January 2008 he was policy director for counterterrorism and strategy at the Homeland Security Council. From January to July 2008 he returned to Iraq as commander of the Joint Special Operations Task Force - Air Directorate.

  In July 2008 Caine became an instructor pilot at the 121st Fighter Squadron. He also became a Special Tactics Air Liaison Officer with the 24th Special Tactics Squadron of the Air Force Special Operations Command, and he stayed in those roles until 2010. From 2009 to 2016 he was a part-time member of the Air National Guard and held several senior positions in the District of Columbia Air National Guard.

  Caine returned to active duty in 2016. Until 2018 he was at once an assistant to the vice commander of US Special Operations Command and assistant commanding general of the Joint Special Operations Command. In 2017 he completed the Joint and Combined Warfighting Course. From 2018 to 2019 he was deputy commanding general of Special Operations Command Central and of the special operations joint task force in Operation Inherent Resolve, the campaign against the Islamic State in Iraq and Syria. From 2019 to 2021 he directed special-access programs in the Office of the Under Secretary of Defense for Acquisition and Sustainment.

  Caine was promoted to three-star lieutenant general in 2021. From November 2021 until December 2024 he served as the Central Intelligence Agency's associate director for military affairs. He retired from the military in 2024.

  By February 2025 he had logged 2,800 flight hours and 150 combat hours. More than 100 of those combat hours were in the F-16, and he had completed two tours in Iraq. His decorations include the Distinguished Flying Cross, the Bronze Star Medal and the Air Medal. Alongside this uniformed record ran a second career, in business.

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• 4. Serial Entrepreneur

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  His own Air Force service biography calls Caine a "serial entrepreneur and investor." In 2010 he founded The Caine Group, an investment and consulting firm that focuses on national security and homeland security.

  He also co-founded RISE Air, an airline company, and served as its chief operating officer. Surf Air acquired RISE Air in 2017. The company is unrelated to the Canadian airline Rise Air.

  His LinkedIn page notes that he has advised Voyager, a space technology company. He is a partner at Ribbit Capital and an advisor for Thrive Capital. In January 2025 he joined Shield Capital, a venture capital firm. Less than two months later, his name was headed to the president.

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• 5. The Nomination

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  On the 21st of February 2025, President Donald Trump named Caine as his nominee to replace Charles Q. Brown Jr. as chairman of the Joint Chiefs of Staff. Trump had already told a story about meeting Caine. Speaking at the 2019 Conservative Political Action Conference, he said they met in Iraq in December 2018. According to Trump, Caine told him, "I love you, sir. I think you're great, sir. I'll kill for you, sir." In the same account, Caine claimed ISIS could be defeated in a week. Trump also said Caine wore a MAGA hat, a detail Caine denied.

  According to The New York Times, Caine met with Trump and Vice President JD Vance during the week before the announcement. The Times later reported that he was considered for the job over Michael Kurilla, the commander of United States Central Command.

  Title 10 of the United States Code sets conditions for the post. The chairman must come from the regular components of the armed forces. The officer must also have served as a combatant, unified, or specified commander, as vice chairman, or as the highest uniformed officer in one of the six service branches. That last requirement may be waived if it is "necessary in the national interest."

  Caine's nomination was sent to the Senate on the 10th of March. He testified before the Senate Committee on Armed Services on the 1st of April. On the 8th of April the committee voted 23-4 to advance him. The full Senate confirmed him on the 11th of April by a vote of 60-25. He was promoted to four-star general before that vote and was sworn in on the 14th of April.

  Maxwell Taylor in 1962 is the only earlier example of a retired general becoming chairman. Taylor had retired in 1959 and was recalled to active duty the year before his appointment. Hugh Shelton, who took the job in 1997, was the last chairman before Caine to arrive without ever having served within the Joint Chiefs. The job tested Caine quickly, beginning with a trip to the southern border.

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• 6. Early Tenure

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  Soon after his confirmation, Caine made an unannounced visit to the Mexico-United States border. There he met troops taking part in the US Northern Command mission supporting Customs and Border Protection. In May 2025 he attended a NATO summit at the alliance's headquarters in Brussels, where he discussed strengthening the alliance. That same month, he privately worried that extending the military campaign against the Houthis in Yemen would strain the supply of assets he viewed as necessary. That concern contributed to Trump's decision to declare victory right away.

  In June, Caine appeared before the Senate Appropriations Subcommittee on Defense. His view of the Russo-Ukrainian war was that Russian president Vladimir Putin would start wars against other countries if he won. That view contradicted Trump's assessment of Putin.

  Trump's claim that the United States was being invaded drew a rejection from Caine. Trump had used that claim as the pretense for his 2025 decision to federalize the California National Guard after protests in Los Angeles. Within the same month, the Twelve-Day War would pull Caine into planning for strikes on Iran.

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• 7. Strikes and Operations

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  Leading up to the June 2025 Twelve-Day War, Caine and John Ratcliffe, the director of the Central Intelligence Agency, gave Trump an assessment from Camp David. It concerned Israel's imminent attack on Iran. Caine and Michael Kurilla, the commander of United States Central Command, then led plans for the US military to strike Iranian nuclear sites in 2025.

  The day after the strike, Caine appeared with defense secretary Pete Hegseth to give details. Caine's description was muted. Hegseth's assertion that the strikes had "obliterated" Iran's nuclear sites mirrored Trump's own wording. At a second press conference with Hegseth days later, Caine focused on the service members who carried out the strike. This was interpreted as an effort to avoid politicizing the military while still serving Trump's interests. According to The Wall Street Journal, the strikes and his follow-up comments helped earn him Trump's trust.

  On the 3rd of January 2026, a US intervention in Venezuela led to the capture of Nicolas Maduro. Caine appeared with Trump and other senior officials at a press conference to report on the operation. Later in January, during the Greenland crisis, Trump asked Caine to present options for using military force to invade and annex Greenland, part of the Kingdom of Denmark. He also asked about the impacts of such a move. Trump ultimately decided against an invasion. A far larger decision came in February.

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• 8. The Iran War

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  During the Iran-United States crisis in February 2026, Caine advised Trump about the risks of a prolonged war with Iran. Trump later denied this. Caine was the only military leader briefing Trump on Iran. He had supported the operation in Venezuela, but he was more hesitant about Iran because of the higher risk of entanglement and American casualties. Even so, he helped convince Trump that such a war was viable.

  Caine's own conclusion owed much to conversations in early February with Lt. Gen. Eyal Zamir, the Israel Defense Forces chief of staff. Zamir, along with Central Command chief Brad Cooper, was critical in convincing him. Zamir, IDF intelligence chief Maj. Gen. Shlomi Binder and Mossad director David Barnea visited Washington to make their case, especially to Caine. Zamir stressed the danger that Iran's ballistic missile program posed to Israel if action was not taken soon. He also argued that the January protests in Iran had created a unique moment of opportunity.

  At the meeting between Trump and Israeli Prime Minister Benjamin Netanyahu in Washington on the 12th of February, Netanyahu presented a four-step plan. Caine and Cooper supported the first two steps. These were the assassination of Ali Khamenei and airstrikes on Iran's ballistic missile and drone programs. They were more hesitant about the last two steps, which were fomenting an uprising and using Kurdish groups to achieve regime change. On the 26th of February, Caine and Cooper briefed Trump on military options. Neither gave him much information about a possible closure of the Strait of Hormuz.

  The Israeli-American war with Iran began on the 28th of February. Caine and Hegseth monitored the US operation with Trump at his Mar-a-Lago resort in Florida. With Cooper's support, Caine kept American forces focused on striking Iran's military capabilities. The goal of regime change, which meant attacks on Islamic Revolutionary Guard Corps leaders and command centers, he left to the Israeli military. Trump called for regime change on multiple occasions during the war. Caine never publicly endorsed it.

  On the 10th of March, Caine acknowledged that Iran was fighting back, though not harder than the United States had expected before the war. During congressional hearings in May, he avoided answering questions about the American military strategy in the war.

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