As of September 3, 2026, Polymarket prices “US strike on Cuba by December 31?” at 11% YES with $5.4M traded. 4 tracked wallets hold a position here; the dominant side is NO.
Trump officials say no imminent military action against Cuba is planned, despite his repeated threats that Havana is next.
Speculation over a potential US strike on Cuba by December 31 intensified through 2026 as President Donald Trump repeatedly warned that "Cuba is next" and suggested American warships deployed in the Middle East for the Iran conflict could return by way of the island. Despite the rhetoric, U.S. officials told The Associated Press in May 2026 that Washington was not looking at imminent military action against Havana. Officials involved in preliminary discussions with Cuban authorities added they were not optimistic the communist government would accept an offer tied to a negotiated de-escalation. [Greenwich Time, May 07]
The pressure campaign has combined diplomatic, economic and military measures. Washington slapped Havana with punishing new sanctions and maintained a near-total blockade on fuel supplies reaching the island, a fuel embargo in place since January 2026. Surveillance activity escalated in parallel, with a surge in spy flights reported over the Caribbean as concerns swelled about whether Washington would invade the nation. In February 2026, leaders from 15 Caribbean and Americas nations meeting at a Caricom summit called for "de-escalation and dialogue," warning against US interventions in the region amid ongoing strikes on suspected drug boats. [Newsweek, May 11]
Contingency planning advanced further in late spring. Senior administration officials reportedly gamed out options through a "tabletop" exercise led by U.S. Southern Command, according to reporting on May 28, 2026, as the White House braced for possible unrest on the island. Pentagon planning for a possible Cuba operation has accelerated as officials prepare for a potential order from Trump, with a sustained military buildup in the Caribbean positioned to enable a rapid move. Whether those preparations translate into an actual US strike on Cuba by December 31 remains contingent on a presidential decision that officials say had not been made, leaving the question of a US strike on Cuba by December 31 unresolved. [Mediaite, May 28]
See which tracked wallets hold this market (entries, size, P&L), the models’ fair value and entry targets — and get an alert within a minute when they trade.
Unlock PRO — $29/mo6/7 models agree on NO, fair value 14c vs market 12c. Weak edge — consider waiting for stronger signal.
| Model | Says | Fair Value estimated fair price | Confidence |
|---|---|---|---|
| MATH PIN Model | NO | 98c | — |
| MATH Compound Signal | NO | 72c | — |
| AI DeepSeek Quant | NO | 91c | 82% |
| AI Grok Contrarian | NO | 78c | 61% |
| AI Gemini Flash | NO | 85c | 85% |
| AI Kimi Macro | NO | 92c | 78% |
| AI Claude Analysis | ??? | — | 0% |
6 of 7 models estimate NO fair value below market (72–98c vs 88c). Gemini Flash leads with 85% confidence.
Models estimate fair value of NO at 86c — market prices it at 88c. 2-point gap supports YES.
All three tracked wallets lean NO, entering between 51c and 61c and now sitting on gains as the market fell to 12c. Their positioning signals smart money sees a US strike on Cuba by year-end as highly unlikely, and the absence of any profitable YES entries suggests no credible counter-bid. Directionally, this cohort's entries argue for further YES decay rather than a reversal.
| Wallet | Category | Side | Amount | P&L | |
|---|---|---|---|---|---|
| 0x0845..6f | MM | NO | $9.8K | +49% | |
| 0x4337..82 | MM | NO | $5.2K | +50% | |
| 0x7c3d..6b | MM | NO | $2.7K | +5% | |
| 0xde7b..4b | MM | YES | $1.2K | -69% |
YES buyers at 41c are deeply underwater as the market repriced to 12c, with 0% of YES positions in profit versus 100% of NO entries at 51-61c now profitable. The 29-point collapse from entry to current price reflects heavy NO-side conviction and leaves YES holders with no cushion, capping any near-term bounce. With NO dominant and profitable, downside pressure toward single digits persists absent a major catalyst.
Polymarket prices YES at 11c with $5.4M in total volume. Our model estimates fair value at 14c. 3-point gap is within normal range — no significant mispricing.
| Platform | YES Price | Volume |
|---|---|---|
| Polymarket | 11c | $5.4M |
| Our Model | 14c | — |