Haiti's transitional government has agreed to pay longtime Donald Trump confidante Roger Stone Jr.'s firm as much as $780,000 a year to lobby in Washington, a deal signed as the Caribbean nation struggles to organize elections amid gang violence, mass displacement and unresolved questions over deportation protections for Haitians in the United States.
A $65,000-a-Month Retainer, Filed Days Ago
Stone registered his work for Haiti through Drake Ventures LLC, the Fort Lauderdale-based consulting and lobbying firm he owns with his wife, Nydia, according to the Miami Herald. The Justice Department filing registering the firm to represent Haiti's Ministry of Foreign Affairs and Worship was submitted on September 16. Under the terms, Drake Ventures will collect a $65,000 monthly retainer, paid out in quarterly installments of $195,000, for a total of $780,000 a year.
The contract runs 12 months, through September 2, 2027, and automatically renews for another year unless either side gives 30 days' notice, the Herald's reporting shows. Stone will report to Raina Forbin, Haiti's minister of foreign affairs and worship, according to POLITICO, in a transitional government led by acting Prime Minister Alix Didier Fils-Aimé. The agreement broadly describes Stone's role as “issue advocacy” and “political activities” before the U.S. government, but does not specify whether the lobbying will focus on elections, security assistance or immigration.
Gangs, Displacement and a Registration Drive That's Barely Moving
Haiti opened 10 voter registration centers across Port-au-Prince on July 30, in neighborhoods considered generally safe, according to WLRN. The turnout has been thin: at one center in Laboule, only three people had signed up an hour after doors opened. Gang violence has displaced more than 1.4 million people nationwide, the station reports, and armed groups control an estimated 70% of the capital and the major roads leading to central regions.
More than half of Haiti's electorate lives in areas affected by gang control, WLRN notes, and an International Crisis Group analyst quoted by the station said the government would not be able to organize elections in territories controlled by gangs. The Haiti Election Tracker from Haiti Policy House similarly flags gang activity, especially in the Ouest Department that includes Port-au-Prince, as a major obstacle, and notes that the country's 316 registered political parties had narrowed to 105 registered entities by an August 14 coalition deadline. Public procedures for overseas voter registration and voting sites for Haitians abroad still had not been finalized, per the same tracker.
Conflicting Calendars, One Certain Deadline in Doubt
The Miami Herald reports Haiti's first round of voting is scheduled for December 13, though the paper describes the election as increasingly doubtful given lagging registration, extended deadlines, poor communication and ongoing gang violence. Other accounts describe different calendars: Africanews reported a revised schedule setting the first round, alongside a constitutional referendum, for December 13, with a runoff on February 21, 2027, while United Nations News had earlier described an electoral calendar placing the first round on August 20, 2026, with a second round and municipal elections on December 6 if needed. The dossier does not resolve which calendar is currently operative.
The human toll behind those numbers is stark by any account. WLRN cites UN figures showing more than 5,900 people killed across Haiti in 2025 and more than 1,600 more from January through March of 2026, while United Nations News separately reported gang violence was associated with more than 8,100 documented killings in 2025 and the displacement of an estimated 1.5 million people. Haiti Policy House put the International Organization for Migration's May 2026 estimate at approximately 1.47 million internally displaced people.
TPS Termination Leaves Hundreds of Thousands in Limbo
Layered onto the election uncertainty is the Trump administration's termination of Temporary Protected Status for Haiti, which POLITICO reports has stripped legal protections from more than 300,000 Haitian nationals in the United States, leaving them vulnerable to deportation.
Stone is far from Haiti's only foreign lobbying arrangement. The Herald notes that security contractors linked to Erik Prince have been assisting a task force overseen by the prime minister's office, and that Haiti previously paid Carlos Trujillo's Continental Strategy $314,940 for work performed between October 17, 2025, and February 5, under a contract POLITICO says was intended to increase U.S. investment in Haiti after Trujillo registered the firm in February 2025.
Wilner Joseph, the presidential candidate of the Viktwa political platform, has been promoting his candidacy by traveling across Haiti by helicopter, according to the Herald's reporting. Whether that campaign, or the broader election timeline, survives the security and logistical hurdles documented by multiple outlets remains an open question as Stone's firm begins its year-long lobbying assignment in Washington.
