The headline from the Wall Street Journal on January 12th read, “Cuba Is Already on the Brink. Maduro’s Ouster Brings It Closer to Collapse,” https://www.wsj.com/world/americas/cuba-venezuela-maduro-impact-7adcefdb?mod=hp_lead_pos9 .
The lede followed:
Elderly Cubans are digging through garbage for scraps of food in Havana. In the country’s second city, Santiago, crowds have gathered, blaring music by Cuban exiles such as Gloria Estefan and Willy Chirino, who sings “Our day is coming soon.” The U.S. ouster of Venezuelan dictator Nicolás Maduro has jolted this country of fewer than 10 million people, which has long relied on Venezuela for oil imports that have barely kept its tiny economy from collapsing.
Since January, without Venezuelan oil, the situation on the island has grown even more dire — even life-threatening. People chop wood or burn charcoal to cook what food they can procure over open fires, and they must wait for a bit of gasoline for months. They cannot depend on reliable power or running water. Medicines are in short supply. Trash piles accumulate in the streets.
As of Friday, March 20, the US appears headed for a standoff with Russia as two Russian oil tankers head toward Cuba and the Trump administration prohibits delivery of the oil. Time will tell how this disagreement plays out.
“U.S. says Cuba is prohibited from taking Russian oil as two tankers head to island” | CNBC, https://www.cnbc.com/2026/03/20/cuba-crisis-fuel-tankers-russia-oil-gas-energy-us-trump.html
Trump now confronts his version of the Cuban Missile Crisis that JFK faced in 1962 — a face-to-face standoff with Russia over Cuba. A new, tense chapter may be about to be opened.
Some older readers will recall the Cuban Missile Crisis, but many others are too young to remember through that history personally. It bears reviewing now.
“The Cuban Missile Crisis, October 1962” | Office of the Historian, US Department of State, https://history.state.gov/milestones/1961-1968/cuban-missile-crisis
On the matter of the US “taking Cuba,” Jeff Harbaugh recently wrote, “When people talk about invading Cuba, I remember this quote … from David Halberstam’s book The Best and the Brightest:”
My understanding has long been that the Cuban ministerial-level government is divided between those willing to change the US-Cuba relationship and those who are afraid or unwilling to change and lose their power. This my opinion only, though it has been informed by the education I received from the three GIC ministerial-level delegations I co-chaired. In my opinion, the general consensus among the Cuban population has been for some time a desire for the regime to change its policies and become closer to the US and to reject Russian influence. Again, in my opinion, after an entire half century of experience, Cubans know that Russian influence has been consistently and continually costly.
I’ve written about Cuba a number of times. Here’s the link to the most recent piece, which contains pertinent history and references.
“Is Cuba Next?” | Kotok Report, https://kotokreport.com/is-cuba-next/
I admit to being jaded about politics. That said, I think Cuba might make a surprise deal — at least it has the option to do so. Admittedly, this is not yet an articulated possibility, as Cuba’s president has vowed to resist a US attempt at a takeover.
“As Trump floats ‘taking Cuba,’ island’s president warns any aggression will be met with ‘impregnable resistance’” | CBS News,
https://www.cbsnews.com/news/as-trump-floats-taking-cuba-islands-president-warns-any-aggression-will-be-met-with-impregnable-resistance
Still, there are three reasons for believing a deal might happen:
1. Secretary of State Rubio wants this. This is his turf, and it has been a primary political goal for years.
2. Cuban leadership is desperate, and a deal is a better choice for them than anything else.
3. Cubans have conversations with the leadership of Venezuela constantly. They see how a changed view can work with President Trump, who is transactional more than ideological. In my opinion, it is in their interest to give Trump a “win.”
I have made four trips to Cuba. Three of them were as chair or co-chair of official GIC delegations that had meetings at ministerial level. In my career I never thought I would be in the central bank in Havana three times in meetings with the leadership and senior staff. I expect those folks will negotiate a deal with the Trump administration if they can do so.
Here’s why. The new leader in Venezuela has skills. She is using them. And the Cuban leaders I met have skills and could follow the Venezuelan example.
The Rubio-led Trump administration policy might just succeed in a negotiated change with Cuban-US relations. I hope so.
This is not about liking Trump or not liking Trump. This is about the best possible outcomes in difficult circumstances. In the present case of Cuba, the decapitation of Maduro in Venezuela has opened the door if the Cuban leaders seize the opportunity and are willing to make the changes required. If they don’t, the island government is collapsing and is destined to become a failed state.
We shall see. When you read this, think about how the new Venezuelan leader is changing her behavior to deal with Trump. She knows that Maduro and his wife had a chance to negotiate and missed the opportunity. The Cubans know it, too.
Trump continues to pressure Cuba to the point of negotiating while Russia and several other countries attempt to aid the island nation. We will be watching this situation closely to see how choices on all sides play out.
Reading List
Current Cuba Situation
“Cuba in communication with US, Cuban diplomat says, as Trump tightens screws” | Reuters, https://www.reuters.com/world/americas/cuba-communication-with-us-cuban-diplomat-says-trump-tightens-screws-2026-02-02/
“Trump says he’ll have ‘honor’ of taking Cuba as country struggles with energy crisis” | ABC News,
https://abcnews.com/Politics/trump-sayshellhave-honor-taking-cuba-country-struggles-withenergycrisis/story?id=131141447“Cuba Is Going Dark” | New York Times,
https://www.nytimes.com/interactive/2026/03/19/world/americas/cuba-blackout-electricity.html?unlocked_article_code=1.UVA.4B-k.qmmYPaH4b1s1&smid=url-share“As Trump floats “taking Cuba,” island’s president warns any aggression will be met with ‘impregnable resistance’” | CBS News,
https://www.cbsnews.com/news/as-trump-floats-taking-cuba-islands-president-warns-any-aggression-will-be-met-with-impregnable-resistance/“Trade with Cuba collapses as Trump escalates pressure on Communist Party leadership” | AP News,
https://apnews.com/article/cuba-trump-rubio-oil-communist-party-745611a2d6fb7e9ba02e322401003a3e“Cuba’s broken economy leaves it at Donald Trump’s mercy” | Economist,
https://www.economist.com/the-americas/2026/03/19/cubas-broken-economy-leaves-it-at-donald-trumps-mercy“Cuba Restores Power After 29-Hour Blackout Amid US Oil Blockade” | US News and World Report,
https://www.usnews.com/news/world/articles/2026-03-17/cuba-reconnects-electrical-grid-but-millions-still-without-power“Cubans say there is little food, power, fuel or relief amid worsening conditions” | NBC News,
https://www.nbcnews.com/world/cuba/cuba-daily-life-shortages-oil-embargo-us-relations-rcna263646“BBC looks at how Cubans are living with fuel shortages” (video) | BBC,
https://www.bbc.com/news/videos/cn0ewj0e7j1o
Assistance Flowing to Cuba
“Russia ships fuel to Cuba using ‘spoofing’ tactic challenging Trump embargo: reports” | FOX News,
https://www.foxnews.com/world/russia-ships-fuel-cuba-using-spoofing-tactic-challenging-trump-embargo-reports“Russian oil tankers close in on Cuba after island’s worst blackout in decades” | Intellinews,
https://www.intellinews.com/russian-oil-tankers-close-in-on-cuba-after-island-s-worst-blackout-in-decades-432425/“Global aid flows to Cuba as energy crisis deepens” | UPI News via MSN,
https://www.msn.com/en-us/news/world/global-aid-flows-to-cuba-as-energy-crisis-deepens/ar-AA1YZTB2“China to help Cuba with solar energy amid US oil blockade and total power outage” | South China Morning Post,
https://www.scmp.com/economy/china-economy/article/3346978/china-help-cuba-solar-energy-amid-us-oil-blockade-and-total-power-outage“Mexico reaffirms support for people of Cuba amid blackouts, oil blockade from U.S.” | KJZZ,
https://www.kjzz.org/fronteras-desk/2026-03-16/mexico-reaffirms-support-for-people-of-cuba-amid-blackouts-oil-blockade-from-u-s“Spain joins growing list of countries sending aid to Cuba amid US chokehold” | Charity Journal,
https://charityjournal.org/spain-joins-growing-list-of-countries-sending-aid-to-cuba-amid-us-chokehold/“Brazil sends approximately one thousand solar panels to Cuba after raising nearly R$190, in an initiative aimed at hospitals and schools that seeks to alleviate an energy crisis marked by frequent blackouts and fuel shortages. – CPG Click Petróleo e Gás” | Now Solar,
https://now.solar/2026/03/18/brazil-sends-approximately-one-thousand-solar-panels-to-cuba-after-raising-nearly-r190-in-an-initiative-aimed-at-hospitals-and-schools-that-seeks-to-alleviate-an-energy-crisis-marked-by-frequent-bla/“Brazil announces the shipment of humanitarian aid to Cuba, including food and agricultural supplies” | CiberCuba,
https://en.cibercuba.com/noticias/2026-03-05-u1-e42839-s27061-nid322256-brasil-anuncia-envio-ayuda-humanitaria-cuba-alimentos#google_vignette
Kotok Report Commentaries about Cuba
“Is Cuba Next?” (January 4, 2026), https://kotokreport.com/is-cuba-next/
“Venezuela, Cuba, Trump Corollary (The New Monroe Doctrine?)” December 16, 2025, https://kotokreport.com/venezuela-cuba-trump-corollary-the-new-monroe-doctrine/
“Cuba Updated” (June 23. 2024), https://kotokreport.com/cuba-updated/
“Cuba Series, Part 4: Helms–Burton & Readers Respond” (March 3, 2024), https://kotokreport.com/cuba-series-4/
“Cuba Series, Part 3: Healthcare” (February 18, 2024), https://kotokreport.com/cuba-series-3/
“Cuba Series, Part 2: US Sanctions on Cuba?” (February 11, 2024), https://kotokreport.com/cuba-series-2/
“Cuba Series, Part 1: The Bay Of Pigs” (February 4, 2024), https://kotokreport.com/cuba-series-1/
Disclosure:
The information posted on this website (including any related blog, podcasts, videos, and social media) reflects the personal opinions, viewpoints, and analyses of David R. Kotok. David R. Kotok is an independent contractor. He may independently receive payments from various entities for consulting, advisory and board functions, speaking fees, book royalties, advertisements in affiliated podcasts, blogs, and emails. Inclusion of such advertisements does not constitute or imply endorsement, sponsorship, or recommendation thereof, or any affiliation therewith, by the Content Creator or by David R. Kotok.
Nothing on this website constitutes investment advice. It should not be construed as an offer soliciting the purchase or sale of any security mentioned. Nor should it be construed as an offer to provide investment advisory services by David R. Kotok. The information provided on this website (including any information that may be accessed through this website) is not directed at any investor or category of investors and is provided solely as general information.
This content, which may contain security-related opinions and/or information, is provided for informational purposes only. Do not rely upon it in any manner as investment advice. It is not an endorsement of any practices, products or services. You should consult your own advisers as to legal, business, tax, and other related matters concerning any investment.
Any charts provided here are for informational purposes only and should not be relied upon when making any investment decision. As always please remember investing involves risk and possible loss. Any projections, estimates, forecasts, targets, prospects, and/or opinions expressed are subject to change without notice and may differ or be contrary to opinions expressed by others. Information in charts has been obtained from third-party sources believed to be reliable; however, David R. Kotok makes no representations about the accuracy of the information.
