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 who rose to become the 22nd chairman of the Joint Chiefs of Staff in 2025. Prior to this role, he served as the associate director for military affairs at the Central Intelligence Agency from 2021 to 2024. He is also a venture capitalist, indicating a career extending beyond solely military service.

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Full Timeline Career & Achievements

October 1990: Commissioned as Second Lieutenant

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

1990: Graduation from Virginia Military Institute

In 1990, John Daniel Caine graduated from the Virginia Military Institute's Air Force Reserve Officer Training Corps.

December 1993: Completion of Euro-NATO Joint Jet Pilot Training Program

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

January 1994: Assignment as F-16 Pilot

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

July 1998: F-16 Instructor Pilot at Andrews Air Force Base

From July 1998 to January 1999, John Daniel Caine was an F-16 instructor pilot and 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, John Daniel 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 Role as F-16 Instructor Pilot

In January 1999, John Daniel Caine ended his role as an F-16 instructor pilot at Andrews Air Force Base, Maryland.

June 1999: Graduation from USAF Weapons School

In June 1999, John Daniel Caine graduated from the USAF Weapons School's Instructor Course as an outstanding graduate.

November 2001: Chief of Group Weapons and Tactics

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

February 2002: End of Role as Chief of Group Weapons and Tactics

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

January 2003: End of Role as Counter-SCUD Project Officer

In January 2003, John Daniel Caine ended his role as a counter-SCUD project officer for U.S. Central Command, at MacDill Air Force Base, Florida.

May 2003: Assigned to Test Center at Tucson Air National Guard Base

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

August 2005: End of Position at Tucson Air National Guard Base

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

2005: White House Fellow

From 2005 to 2006, as part of the White House Fellows program, John Daniel Caine was a special assistant to the United States Secretary of Agriculture and did work related to the response to Hurricane Katrina.

October 2006: Policy Director for Counterterrorism and Strategy

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

2006: Policy Director for Counterterrorism

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

January 2008: Commander of Joint Special Operations Task Force

From January to July 2008, John Daniel 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, John Daniel 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.

July 2008: End of Command of Joint Special Operations Task Force

In July 2008, John Daniel Caine ended his command of the Joint Special Operations Task Force – Air Directorate in Iraq.

2008: End of Term as Policy Director

In 2008, John Daniel Caine ended his term as policy director for counterterrorism within the Homeland Security Council.

2009: Part-Time Member of the Air National Guard

From 2009 to 2016, John Daniel Caine was a part-time member of the Air National Guard and held several senior positions in the District of Columbia ANG.

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

In 2010, John Daniel Caine ended his roles 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 Commanding General of Joint Special Operations Command

From 2016 to 2018, John Daniel Caine served as the assistant commanding general of Joint Special Operations Command.

2016: Assistant Roles in U.S. Special Operations Command

From 2016 to 2018, John Daniel 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: End of Part-Time Membership of the Air National Guard

In 2016, John Daniel Caine ended his time as a part-time member of the Air National Guard.

2017: RISE Air Acquisition

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

2018: Deputy Commanding General Roles

From 2018 to 2019, John Daniel 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.

2018: Deputy Commanding General for Operation Inherent Resolve

From 2018 to 2019, John Daniel Caine was the deputy commanding general for the Operation Inherent Resolve special operations task force.

2019: Director of Special-Access Programs

From 2019 to 2021, John Daniel 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

In November 2021, John Daniel Caine served as the CIA's associate director for military affairs.

2021: Associate Director for Military Affairs at CIA

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

2021: Director of Special-Access Programs

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

December 2024: End of Term as CIA Associate Director

In December 2024, John Daniel Caine's term ended as the CIA's associate director for military affairs.

2024: End of CIA directorship

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

2024: Retirement from the Military

In 2024, John Daniel Caine retired from the military.

January 2025: Joined Shield Capital

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

February 2025: Combat Hours and Tours in Iraq

As of February 2025, John Daniel Caine had accumulated 150 combat hours and two tours in Iraq, with a total of 2,800 flight hours, including more than 100 combat hours in the F-16.

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

In February 2025, President Donald Trump nominated John Daniel Caine as the chairman of the Joint Chiefs of Staff.

May 2025: NATO Summit and Deliberations

In May 2025, John Daniel Caine attended a NATO summit at the organization's headquarters in Brussels, where he deliberated on bolstering the alliance. That month, he privately expressed concerns that extending the military campaign against the Houthis in Yemen would stress supply of assets.

June 2025: Assessment to Trump on Israel's Attack on Iran

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

2025: Flight Hours and Tours in Iraq

As of 2025, John Daniel Caine had accumulated 2,800 flight hours and served two tours in Iraq.

2025: Senate Appropriations Subcommittee on Defense Appearance

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

2025: Chairman of the Joint Chiefs of Staff

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

January 2026: Press Conference on US Strikes in Venezuela

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