Trinidad And Tobago Broke With CARICOM On Cuba – Now Trump Is Sending A Trinidadian National Back Home As US Ambassador

By Staff Reporter | NewsAmericasNow.com

News Americas, WASHINGTON, D.C., Thurs. June 3, 2026: The timing is no coincidence. Days after Trinidad and Tobago broke ranks with CARICOM – reserving its position from the regional body’s statement of concern over escalating US measures against Cuba and aligning itself with Washington through the US-led Shield of the Americas security pact – President Donald Trump has nominated a Trinidad-born former Florida Lieutenant Governor as the next United States Ambassador to Port of Spain.

The nomination of Jennifer Johnson-Carroll, 66, sends a unmistakable diplomatic signal across the Caribbean: countries that align with Washington get rewarded. Countries that don’t – get Kari Lake.

The Reward

Carroll’s biography is extraordinary by any measure. Born in Port of Spain, Trinidad and Tobago, she immigrated to the United States at the age of eight, enlisted in the US Navy in 1979, and served 20 years in uniform – retiring as a Lieutenant Commander in 1999. She went on to become the 18th Lieutenant Governor of Florida – serving from January 2011 to March 2013 under Governor Rick Scott – becoming in the process the first Black person, the first woman, and the first Trinidadian American ever elected to statewide office in Florida, and the first Black Republican elected to Florida statewide office since Reconstruction.

A long-time Trump ally who served as a surrogate during his 2016 presidential campaign and later as a Commissioner on the American Battle Monuments Commission during his first term, Carroll now stands to return to the country of her birth – not as an immigrant child leaving for American shores, but as the United States’ most senior diplomatic representative to the government of Trinidad and Tobago.

The Context: Trinidad’s Strategic Choice

Carroll’s nomination arrives at a moment of significant geopolitical realignment across the Caribbean – one in which Trinidad and Tobago has made a clear and consequential choice about which side of an intensifying US-Cuba confrontation it stands on. When CARICOM foreign affairs ministers expressed their profound concern over escalating US economic and commercial measures against Cuba, Trinidad and Tobago – alongside Guyana – reserved its position. The two nations, both significant energy producers with deep commercial ties to the United States, declined to join the regional consensus in support of Cuba.

Both countries are only 2 of three Caribbean official members of the US-led Shield of the Americas alliance – a security pact signed by 17 Western Hemisphere countries in March 2026 focusing on countering transnational organized crime, drug trafficking, and illegal migration through enhanced intelligence sharing and military cooperation.

The nomination of a Caribbean-born, historically significant diplomat to serve as US Ambassador to Trinidad and Tobago — at precisely this moment of regional fracture – is the kind of diplomatic gesture that Washington makes deliberately and the region understands immediately.

The Contrast With Jamaica

The difference between Washington’s approach to Trinidad and Tobago and its approach to Jamaica could not be more pointed.

For Trinidad – which sided with Washington on Cuba and signed the Shield of Americas pact – Trump nominated a Trinidad-born woman with a historic record of public service, military service, and political achievement who literally grew up in the country she will now represent America within.

For Jamaica d which has not broken with CARICOM on Cuba and which is currently hosting the USS Nimitz in Kingston Harbor in what the US Embassy carefully described as a goodwill visit d Trump nominated Kari Lake. An Arizona-born television anchor with no known connection to Jamaica or the Caribbean and a public record of calling for the mass deportation of immigrants.

The message to the Caribbean is clear. Alignment with Washington opens diplomatic doors. Distance keeps them closed – or worse, puts an anti-immigration hardliner behind them.

A Caribbean Heritage Month Footnote

Carroll’s nomination arrives during Caribbean American Heritage Month – a month the Trump White House has not seen fit to formally recognize with a proclamation. The irony is not lost on Caribbean diaspora observers that the administration’s most symbolically positive gesture toward the Caribbean community in June 2026 is the nomination of a Caribbean-born woman to a diplomatic post – while simultaneously declining to issue the standard recognition of the month dedicated to celebrating Caribbean Americans.

Carroll’s nomination is subject to Senate confirmation.