The story of Desmond Mair Insurance Brokers Ltd. begins with Gerald Mair, whose ambition and a sharp mind for accounting and auditing laid the groundwork for the company. 

The Mair family is traced back to Westmorland. Gerald studied in London at the London Association of Certified Accountants where he obtained first place in the world in 1924. On his return to Jamaica, he placed the first ad in the local newspaper (The Gleaner) on November 20, 1925, announcing his appointment as an insurance agent for The Car & General Insurance Corporation Ltd. of London, England.  

By 1930, he became an Agent for The Sea Insurance Company Ltd., London, England and The Dominion Life Assurance Company of Ontario, Canada.

Gerald was known for his pragmatism, structure, and high standards. Though stern, his discipline and drive set the professional tone for the company’s early years.  After 33 years of leading the business, Gerald passed the baton on to his son Desmond Mair. 

When Desmond Mair took over the business in the late 1950s, he brought a new dimesion to the Company. Desmond’s leadership style brought warmth, charisma, and strong relationship-building skills into the leadership of the company. In the 1970s, he rebranded the company from Gerald Mair & Son to G. Desmond Mair (Insurance) Limited and continued to build on the foundations and global connections his father laid. 

One of the company's most loyal and longstanding staff members who became a cornerstone for the company, Shirley Scott, joined in 1960. She started working with Desmond and later with Gregory and now stands as one of the company’s Shaerholders and Directors.  Despite the economic challenges in the 1970s, Desmond and Shirley carried the company through into the 80’s, preserving its integrity, client base, and core operations. 

Having just returned to Jamaica, Gregory took the reins of the Company after the unexpected passing of his father Desmond. Supported by Shirley, Gregory rose to the challenge. Gregory along with his team navigated the company through the tough economic times in the 1990’s. 

Bringing an engineering background and entrepreneurial mindset, in 2004, Gregory, after 15 years as the Managing Director, changed the status of G. Desmond Mair (Insurance) Ltd. from that of an Agent to a Broker now known today as Desmond Mair Insurance Brokers Ltd. 

Gregory modernized the company. He introduced technology, computerization, and in-house accounting. His leadership emphasized performance and efficiency, while still honoring the deeply personal, service-based legacy of his father and grandfather. 

Gregory has built his reputation through operational excellence and a quiet, focused leadership style that has maintained and ensured the continued growth of the company. 

From global events like World War II, national economic crisis to leadership transitions, Desmond Mair Insurance Brokers Ltd. has stood strong through every major historical challenge over the past century. The continuity of leadership through three generations, combined with long-serving staff like Shirley Scott and Sharon Smith, has allowed the Company to maintain both its organizational culture and reputation.

The Company has always emphasized service, trust, and personal relationships - and while it has evolved, it remains a family business, passed from one generation to the next, staying true to its core values.

Under the leadership of Gregory Mair, Desmond Mair Insurance Brokers Ltd. continues to thrive as a boutique brokerage that values quality above quantity. The company is now looking ahead to the next century, celebrating its 100-year milestone with initiatives by embracing fast expanding technology, whilst remaining focused on personal relationships.

As the team prepares to mark this historic occasion, the legacy of Gerald, Desmond, and Gregory Mair — and the dedication of his team — stands as a testament to the company’s resilience, values, and continued relevance in Jamaica’s Insurance Industry.