Ex-Convict Moves From Port Authority to Governor's Transition Team

Dean Plaskett, who spent a decade in federal prison after conviction on bribery and obstruction charges, occupied a high-ranking position at the Virgin Islands Port Authority before being appointed to lead his cousin's incoming administration, according to records reviewed by the Virgin Islands Free Press.

Plaskett's federal sentence stemmed from his role in a $1.4 million Department of Public Natural Resources contracting scheme. Upon release, he faced a $1.08 million forfeiture judgment. Yet he was placed as Territorial Director of Facilities Management at VIPA, managing airport and port operations across St. Thomas, St. John, and St. Croix.

The Port Authority appointment occurred during the leadership of Carlton Dowe, who was indicted on March 20, 2026, on nine felony counts including bank fraud, false statements on loan applications, and aggravated identity theft. Dowe surrendered his passport and retired immediately from the agency.

Records show Plaskett held two government roles simultaneously: a $45,000 position as Route Match Administrator with the Department of Public Works, and the Port Authority directorship, which sources indicate paid over $100,000 annually. Virgin Islands law generally bars executive branch employees from holding multiple public posts that create conflicts or overlapping pay.

The Port Authority and the Virgin Islands Water and Power Authority keep payroll records confidential through governing board resolutions, unlike other government departments whose staff and salaries appear in the public database. This opacity enabled what the Free Press described as a quiet path back into government for Plaskett.

Governor-elect Stacey Plaskett, Dean Plaskett's cousin, named him Chief of Staff of the Gubernatorial Transition Team. When the appointment drew public backlash, she stated that "he has served his sentence." In this role, Plaskett will lead 14 executive transition subcommittees, evaluate agency performance, review infrastructure audits, and recommend board members and commissioners for multiple government agencies.

Federal prosecutors have charged numerous senior officials from the Bryan-Roach administration, including former Police Commissioner Ray Martinez, OMB Director Jenifer O'Neal, and Housing Finance Director Darin Richardson. Plaskett's Port Authority work proceeded without similar public scrutiny, operating under incoming VIPA director Ava Penn.