Defense Department (“Secretary of Defense Pete Hegseth Statement on General Officer Nominations“):

This evening the President announced that he intends to nominate Lieutenant General Dan “Razin” Caine, USAF, for the position of Chairman of the Joint Chiefs of Staff, the nation’s highest-ranking military officer, and the principal military advisor to the President, Secretary of Defense, and National Security Council.

General Caine embodies the warfighter ethos and is exactly the leader we need to meet the moment. I look forward to working with him.

[…]

Under President Trump, we are putting in place new leadership that will focus our military on its core mission of deterring, fighting and winning wars.

Inside Defense (“Trump fires Brown, picks Caine for Joint Chiefs chairman; CNO, AF vice chief to be replaced“):

The Pentagon announced this evening that President Trump intends to nominate retired Air Force Lt. Gen. Dan “Razin” Caine as chairman of the Joint Chiefs of Staff, replacing Gen. CQ Brown, who has been fired. Chief of Naval Operations Adm. Lisa Franchetti and Air Force Vice Chief Gen. James Slife are also being replaced.

[…]

Trump said Caine, a retired three-star, was “instrumental” in defeating ISIS in his first term, alleging that he had been passed over for promotion in the previous administration.

“Despite being highly qualified and respected to serve on the Joint Chiefs of Staff during the previous administration, General Caine was passed over for promotion by Sleepy Joe Biden,” Trump wrote. “But not anymore! Alongside Secretary Pete Hegseth, General Caine and our military will restore peace through strength, put America First, and rebuild our military.”

Reuters (“‘He’s a real general’: How Trump chose Dan Caine to be top US military officer“):

Dan Caine may not have been on Washington’s radar before Friday night. But President Donald Trump’s fascination with the retired three-star general, his surprise pick to become the next chairman of the Joint Chiefs of Staff, appears to go back to their first meeting in Iraq in 2018.

Caine, then the deputy commander of a special operations task force fighting Islamic State, told the president that the militant group could be destroyed in just a week, Trump recalled during a speech to the Conservative Political Action Conference in 2019.

Since then, he has retold the story about how he met “Razin” Caine multiple times – and the praise has only grown more effusive.

“He’s a real general, not a television general,” Trump said in Miami on Wednesday, two days before his Truth Social post catapulted Caine from retirement to a nomination to be the most senior active-duty officer in the U.S. military.

If approved by the Senate, Caine will take over a military that is reeling from change in the first 30 days of the Trump administration and will inherit a Joint Staff rattled by Trump’s surprise firing of the chairman of the Joint Chiefs of Staff, Air Force General C.Q. Brown.

Caine, a retired F-16 pilot, will be promoted to four-star general, and then have to undergo a potentially grueling Senate confirmation process to get a four-year term as the uniformed head of the nation’s military.

[…]

Caine held a number of posts in the capital from 2005. He was as a special assistant to the secretary at the Department of Agriculture and then policy director for counterterrorism at the White House’s homeland security council.

According to his official Air Force biography, Caine was a part-time member of the National Guard and “a serial entrepreneur and investor” from 2009 to 2016.

He was most recently the associate director for military affairs at the Central Intelligence Agency, before his retirement late last year.

But it was his time in Iraq from 2018 to 2019 that helped him gain Trump’s attention.

Caine will be under particular scrutiny to ensure that he is apolitical, a concern that was heightened by the Friday night firing of Brown, a four-star general. Uniformed military officials are supposed to be loyal to the U.S. Constitution and independent of any party or political movement.

A senior U.S. military official who has worked with Caine for more than a decade said he would seek to keep the military out of politics.

Caine “puts the mission and troops above politics. He is not a political guy,” the official said.
How far Cain can keep the military out of politics may largely depend on Trump – who in the past has dragged the military into partisan issues.

In a recent re-telling of their first meeting in Iraq, Trump said that Caine was in the hangar where service members started putting on “Make America Great Again” hats.

“They all put on the Make America Great Again hat. Not supposed to do it,” Trump said during a speech last year.

“I said, ‘you’re not supposed to do that. You know that.’ They said, ‘It’s OK, sir. We don’t care.’”

NYT (“Dan Caine, Trump’s Joint Chiefs Pick, Had Unusual Path to Top Ranks“):

In President Trump’s telling, Dan Caine, the retired Air Force lieutenant general whom he wants to be his next chairman of the Joint Chiefs of Staff, made an impression on him when the two men first met in 2018.

The general told the president that the Islamic State was not so tough and could be defeated in a week, not two years as senior advisers predicted, Mr. Trump recounted in 2019.

And at a Conservative Political Action Conference meeting last year, Mr. Trump said that General Caine put on a Make America Great Again hat while meeting with him in Iraq. (General Caine has told aides he has never put on a MAGA hat.)

[…]

An F-16 pilot with 150 combat flight hours, General Caine’s career took him on an unusual path for a future Air Force general.

He was a White House fellow at the Agriculture Department and a counterterrorism specialist on the White House’s Homeland Security Council under President George W. Bush. He served in several highly secretive intelligence and special operations assignments, some in the United States and some overseas.

According to his military biography, General Caine was a part-time member of the Air National Guard from 2009 to 2016 and “a serial entrepreneur and investor.”

He was also an associate director for military affairs at the C.I.A. from 2021 to 2024, serving as the principal liaison to the Pentagon and working with the military on several highly classified programs and operations, former colleagues said.

Gen. Kenneth F. McKenzie Jr., a former head of the military’s Central Command, described General Caine in an email as an “exceptionally talented officer.” General McKenzie said he worked closely with the general in his C.I.A. assignment, and that he was “very effective in that job.”

WaPo (“Who is Dan Caine, Trump’s pick as chairman of the Joint Chiefs of Staff?“):

President Donald Trump on Friday said he would appoint retired Air Force Lt. Gen. John Dan “Razin” Caine as chairman of the Joint Chiefs of Staff, replacing Air Force Gen. Charles Q. Brown Jr., a Biden appointee.

[…]

Caine reached the rank of lieutenant general in 2021, and his most recent government role was associate director for military affairs at the CIA.

The three-star ranking is unusual for an appointee to one of the top jobs in the Pentagon. Every previous appointee for chairman of the Joint Chiefs of Staff since 1949 has been either a general or an admiral. Brown led the Air Force before he was appointed, and Gen. Mark A. Milley, his predecessor, had been chief of staff of the Army.

Though, if confirmed, Caine would be promoted to general — and become the highest-ranking officer in the U.S. Armed Forces — while holding the position.

Before joining the CIA, Caine was director of special-access programs at the Pentagon from 2019 to 2021 and a deputy commanding general in the fight against the Islamic State, based in Baghdad in 2018 and 2019. He was commissioned in 1990 and served in various roles in the Air Force over more than two decades, including as a fighter pilot. He has also served in the National Guard.

The nomination is, to say the least, unorthodox.

Nominees for Chairman, by law, must not only already be four-star generals or admirals but they must be serving as head of one of the services or the combatant commands. (A 2018 change that extended the Chairman’s term from two to four years precluded the Vice Chairman from being elevated, as Richard Meyers and Peter Pace had been.) Then again, the law also specifies that a Secretary of Defense must not have been an active duty flag officer in the last seven years and Trump nominated Jim Mattis and Biden nominated Lloyd Austin, anyway, and both were confirmed.

It is also highly unusual for a retired officer to be recalled to active duty and placed in one of the top roles. It is not, however, unprecedented. Off the top of my head, Maxwell Taylor was recalled by President Kennedy to serve as Chairman and Peter Schoomaker was recalled by President George W. Bush to serve as Army Chief of Staff.

Far and away the most unusual issue, though, is that Caine is an Air National Guard officer who apparently owns several businesses on the side. I haven’t fully pieced this together since I was only vaguely aware of him until last night but he served 19 years on active duty and took the unusual (I have literally never heard of it) step of moving to the Guard rather than staying 20 and retiring. He then spent several years in the private sector, apparently doing quite well for himself, before essentially becoming a full-time general officer. (That part is not unusual; Guard and Reserve general and flag officers are often full-time.)

Despite all of that, he will almost certainly be confirmed. While my strong preference would be that a Chairman serve in one of the traditional four-star billets first, Colin Powell, who I consider one of the best ever to serve in that billet, did not. Indeed, he had only held four-star rank four a few months before being nominated to the top job. And, despite the unorthodox detour to the Guard, he has served in quite a number of top billets across a wide swath of the Defense, Intelligence, and other interagency sectors:

• August 2005–September 2006, White House Fellow, Special Assistant to the Secretary, United States Department of Agriculture, Washington, D.C.
• October 2006–January 2008, Policy Director for Counterterrorism and Strategy, White House Homeland Security Council, Executive Office of the President, Washington, D.C.
• January 2008–July 2008, J3 and Commander, Joint Special Operations Task Force – Air Directorate, Balad, Iraq
• July 2008–November 2010, F-16 Instructor Pilot/Mission Commander, 121st FS, Andrews AFB, Md. (July 2008–March 2010, Special Tactics Air Liaison Officer, 24th Special Tactics Squadron, Joint Special Operations Command, Pope AFB, N.C.)
• November 2010–June 2012, Director of Operations (A3)/Deputy Director of Joint Operations (J3), Joint Force Headquarters, District of Columbia ANG, Washington, D.C.
• June 2012–June 2014, Commander, 113th Maintenance Group, Joint Base Andrews, Md.
• June 2014–May 2016, Director of Joint Operations and Training (J3), Joint Force Headquarters, District of Columbia ANG, Washington, D.C.
• May 2016–June 2016, Deputy Commanding General, Air, Joint Force Headquarters, District of Columbia ANG, Washington, D.C.
• June 2016–May 2018, June 2016–May 2018, Assistant to the Vice Commander, U.S. Special Operations Command, Special Operations Command Washington Office, the Pentagon, Arlington, Va. and Assistant Commanding General, Joint Special Operations Command, U.S. Special Operations Command, Fort Bragg, N.C. (concurrently)
• May 2018–September 2019, Deputy Commanding General, U.S. Central Command Special Operations Component and Deputy Commanding General – Special Operations Joint Task Force – Operation Inherent Resolve (Iraq) (concurrently)
• September 2019–September 2021, Director, Special Programs and Director, Special Access Programs Central Office, Va.
• September 2021–November 2021, Special Assistant to the Chief, National Guard Bureau, Washington, D.C.
• November 2021–December 2024, Associate Director for Military Affairs, Central Intelligence Agency, Washington, D.C.

Highlights mine. He has spent a whole lot of time in the National Capitol Region. While highly unconventional—and not really possible anymore for an Active Duty officer—it’s actually pretty strong preparation for the Chairmanship.

That Caine’s path to nomination was making a favorable impression on Trump in the field is amusing but not all that unusual. It’s how Lloyd Austin, who was on nobody else’s radar to be the next Secretary of Defense, got the job. He’d impressed then-Vice President Biden and there was apparently a bond.

Some are making a big fuss over the story about Caine and others in his command wearing MAGA hats and pledging their obsequious fealty to Trump. Caine has denied it. I suspect that the ever-changing tale, which is apparently a staple of Trump speeches, is substantially embellished.