Person of the Year: Michael Cleaver, the former CEO of WINAIR

Person of the Year: Michael Cleaver, the former CEO of WINAIR

WINAIR’s CEO Michael Cleaver gave his all to keep the airline in the sky after Hurricanes Irma and Maria in 2017. He is pictured here next to his temporary container office in 2018, as the WINAIR office was completely destroyed.


In a display of unparalleled dedication and leadership, Michael Cleaver, the retired Chief Executive Officer (CEO) of Windward Islands Airways International NV WINAIR, emerged as a beacon of stability during a pivotal moment in the airline’s history. Originally planning to retire in 2022, Cleaver selflessly extended his tenure by an additional year, ensuring a seamless transition to new management for the national carrier.

  Even as the selection process for a new CEO was underway, Cleaver, with unwavering commitment, provided crucial support to the organization. His steadfast resolve and strategic guidance were instrumental in steering WINAIR through a period of change and uncertainty.

  Finally, on July 1, 2023, after twelve years of dedicated service, Cleaver gracefully relinquished his position at WINAIR. His departure marked the end of an era, but the impact of his leadership would soon become even more apparent.

  Less than six months later, WINAIR’s new CEO, Hans van de Velde, proudly announced a remarkable achievement – the successful repayment of the airline’s US $4,500,000 loan from the Dutch Government. Integral to this loan agreement was the commitment to maintain a minimum of two flights to Saba and Statia, a condition not only met but exceeded by WINAIR. In the past year, the airline successfully operated up to four flights daily on select days of the week.

  Under Cleaver’s operational leadership, WINAIR underwent a remarkable transformation. His vision and relentless efforts facilitated the restructuring and realignment of the airline’s operational processes, aligning them with goals of growth and profitability. Collaborating closely with the Supervisory Board, the CFO, employees and stakeholders, Cleaver achieved exceptional results, attaining profitability in just one year.

  With the dissolution of the Netherlands Antilles on October 10th, 2010, the ownership of WINAIR was transferred to Country St. Maarten with just over 92% interest in the company and to the Netherlands with just under 8%. An adhoc committee led by Michael Ferrier and supported by Roberto Gibbs, Jeroen Veen, and Cleaver, created the conditions to execute new statutes based on book 2 of the Civil Code, followed by the establishment of a new supervisory board of directors in July 2011.

  Georges Alain Greaux became chairman of the supervisory board of directors and, along with his fellow directors Robert Budike and the late Gerrit Draai, started the daunting task of turning the company around by establishing a good management team and plan of action. With the mandate to make the company viable again, Cleaver, a seasoned airline executive, was hired as CEO and President of the company.

  By the first annual general meeting of shareholders in June 2012, all backlogged financial statements were presented, and by the end of 2012, WINAIR became profitable again. This feat was achieved with no capital injection from either shareholders and is a true testament to the management leadership of Cleaver.

  While the region has seen the collapse of many airlines such as ALM, DCA, DAE, BonairExel, Tiara, Cardinal, PAWA, and Insel Air, WINAIR has been able to grow and reinvent itself. Under Cleaver’s leadership, WINAIR navigated challenges posed by Hurricane Irma and the global COVID-19 pandemic, ensuring the continuity of operations and the well-being of employees and customers.

  On September 6, 2017, Hurricane Irma gutted the old office building and damaged WINAIR’s hangar to an extent that it had to be completely rebuilt. After the storm, all aircraft were serviced and operated out of St. Kitts. Once the runway of Princess Juliana International Airport was cleared from debris, WINAIR helped with the evacuation of persons post-Irma via relief flights and also brought in essential relief supplies for the community.

  In October 2017, WINAIR had three Twin Otter aircraft operating a limited schedule from St. Maarten to Saba, Statia, Nevis, and St. Barths. Before Hurricane Irma, the local airline company operated five Twin Otter aircraft. “We will be reintroducing new schedules and introducing new routes as the work with our rebuilding efforts progresses,” Cleaver said at that time, explaining that the airline was working very hard at restoring inter-island connectivity.

  Shortly after, WINAIR announced that it would be resuming flights to Guadeloupe, Dominica, Puerto Rico, Curaçao, and Haiti. These flights were executed using the ATR aircraft operated by Air Antilles. “These aircraft are practically new, just over two years old, and one even one year old,” Cleaver explained at the time.

  After partnering with Air Antilles for five years, WINAIR acquired its own ATR-500 series aircraft in November 2022. The launch of the ATR operation was Cleaver’s crowning achievement. WINAIR proudly unveiled two new ATR-42 aircraft, a substantial expansion and enhancement of its fleet.

  The ATR-500 aircraft are adorned in WINAIR’s own livery, boasting a brand-new interior with 48 comfortable leather seats, introducing a new level of comfort and luxury to its customers. In addition, WINAIR is now able to offer transportation between Curaçao – Aruba, Curaçao – Bonaire, and vice versa.

  WINAIR made a US $1.64 million gross profit in 2022, before taxes. The year 2023 saw further improvement. WINAIR’s turnover in the first quarter of 2023 increased by 35% compared to the same period in 2022. The number of flights increased by 11%, the number of passengers went up by 30%, and the occupancy rate by 19%. WINAIR’s 2023 budget showed a projected profit of US $1.75 million.

  Bidding farewell to CEO Cleaver on July 1, 2023, WINAIR celebrated his success. The company expressed heartfelt gratitude to Cleaver for his outstanding contributions, remarkable achievements, and unwavering dedication. The board, shareholders, employees, and stakeholders united in extending their best wishes for his well-deserved retirement.

  Chairman of the Board George Greaux Jr., who retired a month after Cleaver, said about the CEO: “Michael is the consummate professional you want on board to drive your business successfully. He’s tirelessly passionate in what he does and has taught me so much about the aviation business world that I will be forever grateful for.”

  As WINAIR embarks on an exciting new chapter in 2024, the commitment to connecting Caribbean islands, fostering regional integration, and delivering exceptional service remains unwavering. With the new CEO at the helm, WINAIR is confident in navigating the ever-changing aviation landscape and positioning itself as the preferred choice for travel in the Caribbean. This would not have been possible without the exceptional leadership of Cleaver over the past twelve years. This is why Michael Cleaver has deservedly been chosen as The Daily Herald’s Person of the Year 2023.

The Daily Herald

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