VITEMA’s Deputy Director of Admin & Finance Retires After 30 Years of Service

St. Thomas, U.S. Virgin Islands – The Virgin Islands Territorial Emergency Management Agency (VITEMA) announces the retirement of Deputy Director of Administration and Finance Winston Simon, who has dedicated 30 years of exemplary service to the Government of the Virgin Islands, with the past four years devoted to VITEMA.

A Virgin Islands native and proud product of the public school system, Deputy Director Simon graduated from Charlotte Amalie High School before earning both a Bachelor of Arts in Accounting and a Master of Business Administration from the University of the Virgin Islands.

Deputy Director Winston Simon’s remarkable journey through Virgin Islands public service began in 1997 at the V.I. Department of Health, where he worked in the Federal Grants Management Office. This early experience in federal grants management would prove to be the foundation for a career marked by fiscal excellence, accountability, and unwavering dedication to the people of the Virgin Islands.

In 2000, Deputy Director Simon expanded his expertise by joining the University of the Virgin Islands’ accounting department, further honing his financial management skills in an academic setting. His commitment to continuous growth and professional development led him to the Office of Management and Budget (OMB) in 2004, where he would spend nearly 17 transformative years shaping the territory’s fiscal operations.

At OMB, Deputy Director Simon distinguished himself as a Senior Grants Analyst for nine years, demonstrating exceptional skill in managing federal grants and financial oversight. He completed the Executive Leadership Program through Graduate School USA in 2011, further preparing him for senior management responsibilities.

His outstanding performance earned him the prestigious Employee of the Year award in 2011—a testament to his dedication, expertise, and commitment to excellence. In 2013, he was promoted to Associate Director of Financials, a position he held until December 2020, overseeing critical functions including the federal portion of the executive budget, intergovernmental review of federal programs, government-wide cost allocation plans, and single audits of major federal programs.

In December 2020, Deputy Director Simon brought his wealth of knowledge and experience to VITEMA, joining the agency as Deputy Director of Administration and Finance during a pivotal time in the territory’s emergency management operations. His arrival came as VITEMA continued to navigate post-hurricane recovery efforts while simultaneously preparing for future emergencies and building organizational capacity.

During his tenure at VITEMA, Deputy Director Simon played a vital role in strengthening the agency’s financial infrastructure. He provided testimony before the Virgin Islands Legislature, managed emergency funds with precision, and coordinated a voucher program during the State of Emergency in November 2023. His leadership ensured fiscal accountability and supported the agency’s mission to protect and serve the people of the Virgin Islands.

As Deputy Director of Administration and Finance, Simon became the steward of VITEMA’s fiscal operations, managing multi-million-dollar budgets, ensuring federal financial compliance, and maintaining the agency’s fiscal accountability. His expertise in federal grants management—cultivated over more than two decades—proved invaluable as VITEMA managed complex funding streams from FEMA, the Department of Homeland Security, and other federal partners.

Deputy Director Simon’s responsibilities extended across the full spectrum of financial management, from budget development and execution to financial reporting and audit coordination. He worked diligently to ensure that VITEMA’s financial operations met both territorial and federal standards, maintaining the transparency and accountability that are hallmarks of effective public administration.

His participation in six annual budget hearings before the V.I. Legislature demonstrated his command of VITEMA’s financial landscape, as he provided detailed briefings on personnel allocations, funding sources, and budgetary needs. Whether explaining the complexities of General Fund positions, federal grant allocations, or Emergency Services Fund expenditures, Deputy Director Simon’s clarity and precision helped lawmakers understand the fiscal realities of emergency management operations.

Beyond the spreadsheets and budget documents, Deputy Director Simon understood that sound financial management was essential to VITEMA’s mission of protecting the Virgin Islands community. Every dollar properly stewarded meant resources available for emergency responders, equipment for disaster response, training for personnel, and ultimately, safety for Virgin Islands residents.

VITEMA Director Daryl Jaschen stated, “An agency’s demonstrated fiscal responsibility is derived from managing all funds provided each year by the Governor. Over these past five years, Deputy Director Simon has done just that; he ensured our staff was paid, our vendors were paid, and any local funds expended during a disaster were properly tracked.”

He added, “A particularly rememberable instance of Deputy Director Simon’s dedication occurred in November of 2023, when the legislature, under a Territory State of Emergency, provided funding for 1,288 clean water vouchers to eligible WAPA water customers which were redeemable at five vendor locations on St. Croix. All those vouchers and resulting invoices from the vendors were managed by VITEMA. Deputy Director Simon worked for over six months following the event to ensure the vendors had the vouchers properly reconciled, verified by the VI Office of Management and Budget and received payments through the Department of Finance. Extremely well done.”

As Deputy Director Simon closes this chapter of three decades of public service, he leaves behind a legacy of integrity, professionalism, and dedication to the Virgin Islands community. His career exemplifies the best of public service—a commitment to excellence, a dedication to continuous learning, and an unwavering focus on serving the people of the territory.

The Virgin Islands Territorial Emergency Management Agency extends its deepest gratitude to Deputy Director Winston Simon for 30 years of exemplary service to the Government of the Virgin Islands. His contributions have strengthened the foundation upon which VITEMA operates, and his impact will be felt for years to come.