Loyalists, Pageant Directors And A Country Singer’s Wife

By Staff Writer, NewsAmericas Now

News Americas, New York, NY, Weds. Sept. 16, 2026: President Trump has now nominated five political allies, none of them career Foreign Service officers, to serve as US ambassadors across the English-speaking Caribbean, a pattern that covers nearly every major nation in the region, from Jamaica to Barbados to Trinidad and Tobago.

The latest addition came Monday, when Trump nominated Kimberly Greenwood, wife of country singer Lee Greenwood, to serve as ambassador to Barbados and, without additional compensation, as the top US envoy to six other Eastern Caribbean nations: Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda, Dominica, Grenada, and Saint Vincent and the Grenadines. A former Miss Tennessee who directed the Miss Tennessee, Miss Mississippi and Miss Georgia pageants, Greenwood worked with Trump for 18 years through the Miss Universe Organization, which he formerly owned, a professional relationship that predates her marriage to Greenwood.

“If confirmed by the United States Senate, I will work every day to earn that confidence, to listen and learn, to build genuine relationships,” Greenwood wrote on Instagram, calling the nomination “one of the greatest honors of my lifetime.” Lee Greenwood’s “God Bless the USA” has long served as Trump’s rally walk-up song, and the singer has performed it live at Trump events; the two have also partnered on a Trump-branded Bible line.

Kimberly Greenwood is a former beauty pageant executive with longstanding ties to Trump. According to her husband, country singer Lee Greenwood, she worked with Trump for 18 years while he owned the Miss Universe Organization, directing state pageants. Lee Greenwood, whose signature “God Bless the USA” has long been used at Trump political events, has also maintained a close association with the president. Kimberly Greenwood does not come from the career Foreign Service and, if confirmed by the Senate, would succeed Biden appointee Roger Nyhus in the Barbados and Eastern Caribbean diplomatic post.

A Trinidadian native, and a break with CARICOM

Trinidad And Tobago Broke With CARICOM On Cuba And Now Trump Is Sending Trinidad-Born Former Florida Lieutenant Governor Jennifer Carroll Back Home As US Ambassador

For Trinidad and Tobago, Trump nominated Jennifer Johnson-Carroll, 67, who was born in Port of Spain and migrated to the US at age 8. Carroll built a 20-year US Navy career before entering Florida politics, becoming the state’s 18th Lieutenant Governor from 2011 to 2013, the first Black person, first woman and first Trinidadian American elected to statewide office in Florida. She resigned that post in 2013 amid scrutiny over public relations work for a gambling-linked charity, though the Florida Department of Law Enforcement later found she had broken no laws.

Carroll’s nomination came days after Trinidad and Tobago broke with CARICOM’s collective statement of concern over US measures against Cuba, instead aligning with Washington through the US-led Shield of the Americas security pact, a sequence widely read across the region as a reward for that alignment. If confirmed, Carroll would be the first Trinidad and Tobago-born woman to serve as US ambassador to the country.

Jamaica and the Bahamas round out the pattern

Trump has separately nominated former Senate candidates Kari Lake of Arizona to serve as ambassador to Jamaica and Herschel Walker of Georgia to serve as ambassador to the Bahamas, both prominent Trump-backed political figures rather than career diplomats. The pattern extends beyond the Caribbean as well: Charles Kushner, father of Trump’s son-in-law Jared Kushner, serves as ambassador to France and Monaco, while Kimberly Guilfoyle, a former Fox News host who previously dated Trump’s eldest son, was chosen as ambassador to Greece.

A Washington Post review last month found the Trump administration has filled a larger-than-usual share of its ambassadorial posts with political supporters rather than career Foreign Service officers, with many posts across the government still unfilled.

All nominations require Senate confirmation before taking effect.

NewsAmericasNow will continue tracking US ambassadorial appointments affecting the Caribbean.

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