Rise to Success: Career Highlights of Dan Caine

From career breakthroughs to professional milestones, explore how Dan Caine made an impact.

John Daniel "Raizin" Caine is an American general and venture capitalist. He rose to prominence, ultimately becoming the 22nd chairman of the Joint Chiefs of Staff in 2025. Previously, he served as the associate director for military affairs at the Central Intelligence Agency from 2021 to 2024, showcasing his experience in both military and intelligence sectors.

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Full Timeline Career & Achievements

1959: Maxwell Taylor Retired

In 1959, Maxwell Taylor retired.

1962: Maxwell Taylor Served as Chairman

In 1962, Maxwell Taylor served as chairman after being recalled to active duty.

October 1990: Commissioned as Second Lieutenant

In October 1990, Caine was commissioned as a second lieutenant through the Virginia Military Institute's Air Force Reserve Officer Training Corps.

December 1993: Completed Euro-NATO Joint Jet Pilot Training Program

In December 1993, Caine completed the Euro-NATO Joint Jet Pilot Training Program at Sheppard Air Force Base, Texas, as a distinguished graduate.

January 1994: F-16 Pilot in the 138th Fighter Squadron

In January 1994, Caine was selected to be an F-16 pilot in the 138th Fighter Squadron at the Syracuse New York Air National Guard Base.

1997: Hugh Shelton Served within the Joint Chiefs of Staff

In 1997, Hugh Shelton served within the Joint Chiefs of Staff.

July 1998: F-16 Instructor Pilot

From July 1998 to January 1999, Caine was an F-16 instructor pilot and the chief of weapons for the 121st Fighter Squadron at Andrews Air Force Base, Maryland.

July 1998: End of Assignment as F-16 Pilot

In July 1998, Caine's assignment as an F-16 pilot in the 138th Fighter Squadron at the Syracuse New York Air National Guard Base ended.

January 1999: End of Assignment as F-16 Instructor Pilot

In January 1999, Caine's assignment as an F-16 instructor pilot and the chief of weapons for the 121st Fighter Squadron at Andrews Air Force Base, Maryland ended.

June 1999: Graduated from USAF Weapons School

In June 1999, Caine graduated from the USAF Weapons School as an outstanding graduate.

November 2001: Chief of Group Weapons and Tactics

From November 2001 to February 2002, Caine was the chief of group weapons and tactics for the 332nd Air Expeditionary Wing in Kuwait.

February 2002: Chief of Group Weapons and Tactics

In February 2002, Caine ended his service as the chief of group weapons and tactics for the 332nd Air Expeditionary Wing in Kuwait.

January 2003: Counter-SCUD Project Officer

Until January 2003, Caine was a counter-SCUD project officer for U.S. Central Command, at MacDill Air Force Base, Florida.

May 2003: Assigned to Test Center

In May 2003, Caine was assigned to the Test Center at the Tucson Air National Guard Base, Arizona, as its head of operations.

2004: Completed Air Command and Staff College

In 2004, Caine completed the Air Command and Staff College by correspondence.

August 2005: End of Position at Test Center

In August 2005, Caine ended his position as the head of operations at the Test Center at the Tucson Air National Guard Base, Arizona.

2005: Special Assistant to the United States Secretary of Agriculture

From 2005 to 2006, as part of the White House Fellows program, Caine was a special assistant to the United States Secretary of Agriculture.

October 2006: Policy Director at Homeland Security Council

From October 2006 to January 2008, Caine was the policy director for counterterrorism and strategy at the Homeland Security Council.

2006: Policy Director for Counterterrorism

From 2006 to 2008, Caine served within the Homeland Security Council as a policy director for counterterrorism.

January 2008: Policy Director at Homeland Security Council

In January 2008, Caine ended his service as policy director for counterterrorism and strategy at the Homeland Security Council.

July 2008: Commander of Joint Special Operations Task Force

From January to July 2008, Caine was the commander of the Joint Special Operations Task Force – Air Directorate in Iraq.

July 2008: Instructor Pilot and Special Tactics Air Liaison Officer

In July 2008, Caine became an instructor pilot at the 121st Fighter Squadron and a Special Tactics Air Liaison Officer at the 24th Special Tactics Squadron of the Air Force Special Operations Command.

2008: Policy Director for Counterterrorism

In 2008, Caine ended his service as policy director for counterterrorism in the Homeland Security Council.

2009: Part-Time Member of Air National Guard

From 2009 to 2016 Caine was a part-time member of the Air National Guard.

2010: End of Roles as Instructor Pilot and Special Tactics Air Liaison Officer

In 2010, Caine ended his service as an instructor pilot at the 121st Fighter Squadron and a Special Tactics Air Liaison Officer at the 24th Special Tactics Squadron of the Air Force Special Operations Command.

2010: Founded The Caine Group

In 2010, John Daniel Caine founded The Caine Group, an investment and consulting firm focusing on national security and homeland security.

2016: Assistant to Vice Commander of U.S. Special Operations Command

From 2016 to 2018, Caine was simultaneously an assistant to the vice commander of the U.S. Special Operations Command and the assistant commanding general of the Joint Special Operations Command.

2016: Assistant Commanding General of Joint Special Operations Command

From 2016 to 2018, Caine was the assistant commanding general of Joint Special Operations Command.

2016: End of Air National Guard

In 2016 Caine's service as a part-time member of the Air National Guard ended.

2017: Completed Joint and Combined Warfighting Course

In 2017, Caine completed the Joint and Combined Warfighting Course.

2017: RISE Air Acquired by Surf Air

In 2017, RISE Air, an airline company co-founded by Caine, was acquired by Surf Air.

December 2018: Met Trump in Iraq

In December 2018, Trump met Caine in Iraq.

2018: Deputy Commanding General

From 2018 to 2019, Caine simultaneously served as a deputy commanding general of Special Operations Command Central and of the special operations joint task force in Operation Inherent Resolve.

2019: Director of Special-Access Programs

From 2019 to 2021, Caine was the director of special-access programs in the Office of the Under Secretary of Defense for Acquisition and Sustainment.

November 2021: Associate Director for Military Affairs at the CIA

From November 2021 until December 2024, Caine served as the CIA's associate director for military affairs.

2021: Director of Special-Access Programs

In 2021, Caine ended his service as the director of special-access programs in the Office of the Under Secretary of Defense for Acquisition and Sustainment.

2021: Associate Director for Military Affairs at CIA

In 2021, John Daniel "Raizin" Caine became the associate director for military affairs at the Central Intelligence Agency.

December 2024: Associate Director for Military Affairs at the CIA

In December 2024, Caine ended his service as the CIA's associate director for military affairs.

2024: Retired from the Military

In 2024, Caine retired from the military.

2024: Associate Director for Military Affairs at CIA

In 2024, John Daniel "Raizin" Caine ended his service as the associate director for military affairs at the Central Intelligence Agency.

January 2025: Joined Shield Capital

In January 2025, Caine joined Shield Capital, a venture capital firm.

February 2025: Combat Hours

As of February 2025, Caine has 150 combat hours and two tours in Iraq.

February 2025: Nominated as Chairman of the Joint Chiefs of Staff

In February 2025, President Donald Trump named Caine as his nominee as the chairman of the Joint Chiefs of Staff.

May 2025: Attended NATO Summit

In May 2025, Caine attended a NATO summit at the organization's headquarters in Brussels.

June 2025: Assessment on Israel's Imminent Attack on Iran

Leading up to the June 2025 Twelve-Day War, Caine and John Ratcliffe gave an assessment to Trump on Israel's imminent attack on Iran from Camp David.

2025: Flight Hours

As of 2025, Caine has 2,800 flight hours.

2025: Became 22nd Chairman of the Joint Chiefs of Staff

In 2025, John Daniel "Raizin" Caine became the 22nd chairman of the Joint Chiefs of Staff.

2025: Senate Appropriations Subcommittee on Defense

In June 2025, Caine appeared before the Senate Appropriations Subcommittee on Defense, offering a view of the Russo-Ukrainian war that suggested that if victorious, Russian president Vladimir Putin would initiate wars against other countries.

January 2026: U.S. Strikes in Venezuela

Following the 3 January 2026 U.S. strikes in Venezuela and the capture of Nicolás Maduro, Caine appeared alongside President Trump and other senior officials in a press conference to report on the operation.