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Third time unlucky?
Jamaican-born American Dale Holness facing an uphill climb
News
By Harold G Bailey Observer write  
June 8, 2026

Third time unlucky?

Tide turns against Holness in latest bid to enter US Congress

NEW YORK, USA — Disappointed! That’s how Dale Holness, the Jamaican-born businessman and politician who is making a third bid for Florida’s 20th Congressional District, described his feelings regarding the decision by his fellow Democrat, Congresswoman Debbie Wasserman Shultz, to contest that district.

Wasserman Shultz, who currently represents a different district, has decided to run in the heavily black democratic 20th district, following a realignment of district lines as a result of redistricting exercises which have been roiling the political landscape in the United States for several months.

In an interview with the Jamaica Observer, Holness said he believes that Shultz, a 21-year veteran of Congress, should contest her 22nd congressional district, given her vast campaign cash on hand of US$2.5 million and her long association with that district.

“This could also ensure that Democrats have a better chance of gaining more seats in the State as she would be a stronger candidate,” Holness argued.

Published polls by Wasserman Shultz’s campaign have shown that Shultz, who is white, is being viewed favourably by black voters who make up nearly 50 per cent of voters in the 20th district where many Jamaicans and other Caribbean nationals reside.

While not dismissing the polls entirely, Holness said the results depend on who had been polled and, more importantly, on how poll questions had been posed.

He said that Wasserman Shultz’s decision to enter the contest in the 20th district has “caused a split and has left some in the black community very angry and concerned”.

He noted, however, that “Discussions are currently ongoing in a bid to coalesce efforts around one black candidate, and it is likely that a resolution could be reached by Monday [today] as it is possible that some candidates may decide to quit the race.”

According to Holness, two of the black candidates had already withdrawn from the contest, one of whom he said would be running in a different district.

The decision by Wasserman Shultz, whom Holness said he has worked with on a few projects, has raised questions about the future of black representation in Congress.

“At the same time, I do acknowledge that everyone has the right to offer themselves to serve once they meet the requirements. While I am concerned about the situation, I am not overly worried. God has been good to me and I am grateful,” said Hanover-born Holness.

Jamaican fans of Dale Holness show their support for the would-be congresman.contributed

Jamaican fans of Dale Holness show their support for the would-be congresman.

He said that “from all indications, Wasserman Shultz was adamant she would remain in the race to represent the district”.

Prior to her decision and the redistricting exercise, Holness was leading the field in fund-raising in the first quarter, with US$312,000 which he said did not include any contribution from any political action committee (PAC).

Filing with the Federal Election Commission (FEC) shows that PACs contributed over US$500,000 to Wasserman Shultz’s campaign.

On whether he would consider withdrawing from the race, Holness said: “If I thought there was a stronger candidate I would consider doing so.

“This district needs someone who understands the needs of the people and who has always been with them. I have worked with the people of this district, I understand their needs, I have never left them — even when things became tough — and I have broad plans to improve the quality of their lives,” he said.

Holness, who has served as a commissioner and mayor of Broward County, first attempted to represent the district in a 2021 special election, losing by an agonising five votes to Shelia Cherfilus McCormick. Vastly outspent by McCormick a year later, Holness again lost his bid to represent the district.

McCormick, who resigned from Congress in April this year after facing ethics charges, has indicated she is planning to run again in the 20th district, although she was indicted by a grand jury on fraud charges.

She is accused of misusing US$5 million in disaster funds from the Federal Emergency Management Agency (FEMA) and using part of the money to fund her 2022 campaign. McCormick has consistently denied the allegations.

Whoever wins the August 18 primary is virtually assured of winning the general election in November 2026 to represent the district. For Holness, should he succeed in his bid to be elected it would be historic, as he would become the first Jamaican-born national to be elected to the United States Congress.

Yvette Clarke, the daughter of Jamaican immigrant Una Clarke, is the representative for Congressional District 9 in New York, but was born in the US.

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