As of September 3, 2026, Polymarket prices “US strike on Cuba by December 31?” at 14% YES with $5.2M traded. 3 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/mo5/5 models agree on NO, fair value 17c vs market 14c. Weak edge — consider waiting for stronger signal.
| Model | Says | Fair Value estimated fair price | Confidence |
|---|---|---|---|
| MATH PIN Model | NO | 97c | — |
| MATH Compound Signal | NO | 70c | — |
| AI DeepSeek Quant | NO | 90c | 72% |
| AI Grok Contrarian | NO | 75c | 55% |
| AI Gemini Flash | NO | 82c | 80% |
5 of 5 models estimate NO fair value below market (70–97c vs 86c). Gemini Flash leads with 80% confidence.
Models estimate fair value of NO at 83c — market prices it at 86c. 3-point gap supports YES.
We tracked 3 wallets with positions above $1K on this market. 3 market makers are providing $18K in liquidity, primarily on NO. NO wallets entered between 52c–61c.
| Wallet | Category | Side | Amount | P&L | |
|---|---|---|---|---|---|
| 0x0845..6f | MM | NO | $11.3K | +54% | |
| 0x4337..82 | MM | NO | $5.1K | +45% | |
| 0xde7b..4b | MM | YES | $1.5K | -63% |
YES wallets entered between 41c, NO wallets at 52c–61c. At current price 14c, all YES buyers are underwater while all NO holders are profitable. Profitable positions rarely sell early — NO side has structural price support.
Polymarket prices YES at 14c with $5.2M in total volume. Our model estimates fair value at 17c. 3-point gap is within normal range — no significant mispricing.
| Platform | YES Price | Volume |
|---|---|---|
| Polymarket | 14c | $5.2M |
| Our Model | 17c | — |