File the date: August 6, 2026. The reporting broke Wednesday night; within eighteen hours, the online debate had already narrowed to a single word — invasion — while the document in front of everyone described something else entirely.
Note which mistake this is. It is the mistake of reading a covert operation by its worst-case shape instead of its actual design. Historians make this error constantly with 1930s appeasement debates — people ask “will there be war,” when the operative question was always narrower: which institutions get hollowed first, and who benefits from the hollowing. Jack is correct to separate the roster from the rumor. A task force staffed with case officers, cyber specialists, and influence operators is not a landing force. It is, as he names it, a persuasion shop — and persuasion shops have a long, well-documented history of achieving what militaries cannot.
The historical parallel worth naming precisely is not 1961. It is 1953 and 1954 — Iran and Guatemala. In both operations, the CIA did not invade. It identified a fracturable elite, applied economic pressure until the fracture widened, and then offered the wobbling faction an exit that looked like their own idea. Mossadegh and Árbenz were not defeated by soldiers. They were defeated by the isolation of a small number of people who calculated, under pressure, that switching sides cost less than loyalty. That is the mechanism Jack is describing in Havana in 2026, run by a different generation of the same institution.
There is an older version of this pattern still, one from a country the task force is not aimed at but sits adjacent to on the priority list. Soviet doctrine called it “active measures” — not sabotage of infrastructure, but sabotage of cohesion, executed by finding the officials who already doubted the system and giving them a reason to act on the doubt. The tool is old. Empires have used it since Rome bought Gallic chieftains rather than fighting their tribes. What changes across centuries is only the sophistication of the targeting, not the logic.
Jack is correct on the second point too, and it is the sharper one: attention is finite, and an agency that adds a fourth top-tier priority without adding people is not expanding. It is reallocating, quietly, from somewhere. Note what doesn’t require speculation here — the Russia desk was already thinning before this reporting broke. The arithmetic he describes is the same arithmetic that preceded American intelligence failures before, most notably in the run-up to 2001, when resources chasing an old priority went unrenewed while a new one absorbed the attention that should have covered both.
File this too, because it is the discipline history rewards and journalism often skips: the postscript about the word “limited.” Every operation that later expanded had a limited mandate at its outset — Vietnam’s advisory mission, the Guatemalan operation itself, which was authorized as covert psychological pressure and became a coup within a year. Limited is not a ceiling. It is a starting position, and only the passage of time reveals which one it was.
What doesn’t change, regardless of how this particular operation unfolds: elites under economic pressure fracture in predictable ways, agencies with finite officers rob one priority to feed another, and operations authorized quietly tend to expand quietly, because the quiet was the design, not an accident of the reporting.
Jane...you're right that it's '53 and '54, not '61.
The Bay of Pigs is the one everyone reaches for...because it's the one that failed LOUDLY. The ones that worked...yeah...they don't come with a beach to name them after.
Tks Jack. Keep up the truthful analytic reporting. I can’t get my friends to see the simple common logic you provide us.
Those friends of mine are either to stuck on details that throw up a smoke screen of discontent without any thing they can do about it while you provide the simple truth which can be acted on.
On the friends...don't push. One piece...once...no follow-up. People decide when they're ready to look...not when we're ready for them to. I wish I could say otherwise.
The ones who come around...usually do it quietly...months later...and never mention WHAT changed their mind.
Jack, what does Cuba offer to trump? Other than a throat punch to putin? We don't offer help to our own states and territories, so why in the Hell are we sticking our nose in? Or is it because Rubio sees himself as his homeland's savior?
Sue P...fair question...and the reporting gives PARTIAL answers.
Rubio's the loudest one...Cuban-American, called it a "major priority," and he's seen...by many...as the architect. Being ninety miles from Florida...with a Chinese listening post on it...that sure doesn't hurt either.
BUT...look at what the analysts were actually told to hunt: financial movements and business dealings of regime leadership. That's NOT ideology. That's ASSET MAPPING.
As for Puerto Rico...you're pointing at something very real. Attention is finite there...too.
Stay tuned...I think this will develop into a MUCH bigger story...soon.
Thanks Jack…this is incredibly unnerving…this is the gang that “can’t shoot straight,” who have so screwed up on Iran and now they’re going to go after Cuba…good God!
So I’m curious….. since there is asset mapping, is the regime looking at this as ‘national security’? If it’s not, I’m having a hard time seeing strategic value… If Cuba is resources rich, that has completely flown by me…. My brain is sorta fried today.. so I hope that is not a dumb question.
Since I don’t know how the CIA is organized, is it possible the extra load is simply parceled out to current staff? I’m guessing there would be some expertise lag at the region level? When I was in the corporate world, that’s exactly what would happen. Didn’t matter if the person getting the extra work knew the subject matter….. and that presents its own set of issues. I’m hoping intelligence is smarter than that but…. in the current environment….
There is so much going on in the world, I’m having a hard time keeping up with it all. So grateful for these articles. Thanks Jack.
Cuba isn't resource-rich in any way...that justifies this. Nickel and cobalt...and some offshore oil that's never panned out. NOTHING worth a task force.
Which is why the ASSET MAPPING...reads differently.
Tracking leadership's money isn't about national resources. It's about individual EXPOSURE; what each person stands to LOSE...and...what could be OFFERED back.
A different kind of move. Leverage on PEOPLE...not on a COUNTRY.
Your corporate instinct/gut... is exactly right. That's EXACTLY how it works...and your concern about EXPERTISE LAG...is the correct concern.
Regional knowledge isn't transferable; language...decades of history...source relationships. Somebody covering an unfamiliar file...isn't just SLOWER...they ALSO miss things they don't KNOW to look for.
You're keeping up fine. Nobody's keeping up with all of it...believe me.
A new "Oh look over here"; another situation to capture media and people's attention so that they stop focusing on all that is already happening. Too many balls in the air for people to process.
So here is the strategy as I understand it. We cause the pain -block oil imports. Then we ask the "leadership" to trust us to remove the pain . This from an administration that has lied continuously for almost two years now. Not a great backdrop for trust, in my opinion.
File the date: August 6, 2026. The reporting broke Wednesday night; within eighteen hours, the online debate had already narrowed to a single word — invasion — while the document in front of everyone described something else entirely.
Note which mistake this is. It is the mistake of reading a covert operation by its worst-case shape instead of its actual design. Historians make this error constantly with 1930s appeasement debates — people ask “will there be war,” when the operative question was always narrower: which institutions get hollowed first, and who benefits from the hollowing. Jack is correct to separate the roster from the rumor. A task force staffed with case officers, cyber specialists, and influence operators is not a landing force. It is, as he names it, a persuasion shop — and persuasion shops have a long, well-documented history of achieving what militaries cannot.
The historical parallel worth naming precisely is not 1961. It is 1953 and 1954 — Iran and Guatemala. In both operations, the CIA did not invade. It identified a fracturable elite, applied economic pressure until the fracture widened, and then offered the wobbling faction an exit that looked like their own idea. Mossadegh and Árbenz were not defeated by soldiers. They were defeated by the isolation of a small number of people who calculated, under pressure, that switching sides cost less than loyalty. That is the mechanism Jack is describing in Havana in 2026, run by a different generation of the same institution.
There is an older version of this pattern still, one from a country the task force is not aimed at but sits adjacent to on the priority list. Soviet doctrine called it “active measures” — not sabotage of infrastructure, but sabotage of cohesion, executed by finding the officials who already doubted the system and giving them a reason to act on the doubt. The tool is old. Empires have used it since Rome bought Gallic chieftains rather than fighting their tribes. What changes across centuries is only the sophistication of the targeting, not the logic.
Jack is correct on the second point too, and it is the sharper one: attention is finite, and an agency that adds a fourth top-tier priority without adding people is not expanding. It is reallocating, quietly, from somewhere. Note what doesn’t require speculation here — the Russia desk was already thinning before this reporting broke. The arithmetic he describes is the same arithmetic that preceded American intelligence failures before, most notably in the run-up to 2001, when resources chasing an old priority went unrenewed while a new one absorbed the attention that should have covered both.
File this too, because it is the discipline history rewards and journalism often skips: the postscript about the word “limited.” Every operation that later expanded had a limited mandate at its outset — Vietnam’s advisory mission, the Guatemalan operation itself, which was authorized as covert psychological pressure and became a coup within a year. Limited is not a ceiling. It is a starting position, and only the passage of time reveals which one it was.
What doesn’t change, regardless of how this particular operation unfolds: elites under economic pressure fracture in predictable ways, agencies with finite officers rob one priority to feed another, and operations authorized quietly tend to expand quietly, because the quiet was the design, not an accident of the reporting.
#HOLDFAST
Jane...you're right that it's '53 and '54, not '61.
The Bay of Pigs is the one everyone reaches for...because it's the one that failed LOUDLY. The ones that worked...yeah...they don't come with a beach to name them after.
Thank you for this, Jane.
-Jack
... And because it's Cuba again.
Oh boy -- this should be immediately obvious to someone who knows how to look at reporting that's directly in front of them. I didn't spot it either.
Thanks to you for underlining what was important and what was omitted from the reporting of this story.
J.B....I appreciate that.
Honestly, I read past it the first time, too; the four job titles are sitting RIGHT THERE...in the second paragraph...and I scrolled by them.
That's how it works. The thing hiding...in PLAIN SIGHT...is doing that on purpose.
Thanks for reading closely, J.B. Levin!
-Jack
Tks Jack. Keep up the truthful analytic reporting. I can’t get my friends to see the simple common logic you provide us.
Those friends of mine are either to stuck on details that throw up a smoke screen of discontent without any thing they can do about it while you provide the simple truth which can be acted on.
John...thank you.
On the friends...don't push. One piece...once...no follow-up. People decide when they're ready to look...not when we're ready for them to. I wish I could say otherwise.
The ones who come around...usually do it quietly...months later...and never mention WHAT changed their mind.
Glad you're here in the fight, John!
-Jack
You’re the best. And good advice on the friends. And I’m glad you’re here to guide us on.
Jack, what does Cuba offer to trump? Other than a throat punch to putin? We don't offer help to our own states and territories, so why in the Hell are we sticking our nose in? Or is it because Rubio sees himself as his homeland's savior?
Sue P...fair question...and the reporting gives PARTIAL answers.
Rubio's the loudest one...Cuban-American, called it a "major priority," and he's seen...by many...as the architect. Being ninety miles from Florida...with a Chinese listening post on it...that sure doesn't hurt either.
BUT...look at what the analysts were actually told to hunt: financial movements and business dealings of regime leadership. That's NOT ideology. That's ASSET MAPPING.
As for Puerto Rico...you're pointing at something very real. Attention is finite there...too.
Stay tuned...I think this will develop into a MUCH bigger story...soon.
-Jack
Thanks Jack…this is incredibly unnerving…this is the gang that “can’t shoot straight,” who have so screwed up on Iran and now they’re going to go after Cuba…good God!
Christie...I hear you.
Though...I'd offer this: the worry isn't that they'll fumble it. It's that THIS particular play...has a LONG record of working.
Either way, Christie...you're paying attention...and THAT is the part YOU control. And that... is most of what steadiness is!
-Jack
So I’m curious….. since there is asset mapping, is the regime looking at this as ‘national security’? If it’s not, I’m having a hard time seeing strategic value… If Cuba is resources rich, that has completely flown by me…. My brain is sorta fried today.. so I hope that is not a dumb question.
Since I don’t know how the CIA is organized, is it possible the extra load is simply parceled out to current staff? I’m guessing there would be some expertise lag at the region level? When I was in the corporate world, that’s exactly what would happen. Didn’t matter if the person getting the extra work knew the subject matter….. and that presents its own set of issues. I’m hoping intelligence is smarter than that but…. in the current environment….
There is so much going on in the world, I’m having a hard time keeping up with it all. So grateful for these articles. Thanks Jack.
Deb...NOT a dumb question; it's the RIGHT one.
Cuba isn't resource-rich in any way...that justifies this. Nickel and cobalt...and some offshore oil that's never panned out. NOTHING worth a task force.
Which is why the ASSET MAPPING...reads differently.
Tracking leadership's money isn't about national resources. It's about individual EXPOSURE; what each person stands to LOSE...and...what could be OFFERED back.
A different kind of move. Leverage on PEOPLE...not on a COUNTRY.
Your corporate instinct/gut... is exactly right. That's EXACTLY how it works...and your concern about EXPERTISE LAG...is the correct concern.
Regional knowledge isn't transferable; language...decades of history...source relationships. Somebody covering an unfamiliar file...isn't just SLOWER...they ALSO miss things they don't KNOW to look for.
You're keeping up fine. Nobody's keeping up with all of it...believe me.
Thank you, Deb...truly.
-Jack
A new "Oh look over here"; another situation to capture media and people's attention so that they stop focusing on all that is already happening. Too many balls in the air for people to process.
Interesting to see if church groups or university study programs are still having Cuban programs in this timeframe.
I don’t think I have anything to add here. You guys are paying enough attention to cover what remarks I’d have had. Carry on, friends.
#HoldFast
Same here.
So here is the strategy as I understand it. We cause the pain -block oil imports. Then we ask the "leadership" to trust us to remove the pain . This from an administration that has lied continuously for almost two years now. Not a great backdrop for trust, in my opinion.
Cuba is in the DARK because they ran out of oil
They ran out of oil because the Strait is closed, and " we" closed it.
America is using its Strategic OIL RESERVES. Some oil from Canada, but Trump slapped 50% tariff, and more expensive.
Speculating oil runs out people panic, protest, Trump uses insurrection act.
Hope not, but he never met a protest he didn't like and just calls it a crisis.🗽🇺🇲🇺🇦
https://substack.com/@nk23/note/c-309120122?r=1n30w
Article on Flock cameras, which turned to look like bait and switch.