Dennis Lalor was a Chartered Insurer, the Founder, Chairman and Chief Executive Officer of the ICWI Group Limited and its subsidiaries, which he built into one of the largest full-service financial institutions in the Caribbean. Lalor has received numerous awards and citations for service to Jamaica including the Order of Jamaica in 1994.
Glen Laman interviewed Lalor in 2013 while researching Jamaican Entrepreneurs.
Dennis Lalor was born in Kingston, Jamaica in 1934. He died on May 14, 2026. His parents were Gerald and Daisy (Dryden) Lalor. His father was a merchant and wholesaler with a business in the Crossroads area of Kingston. His father’s mother was Jewish, but his father was an Anglican and a brilliant organist who played in the synagogue on Saturday and in the Anglican Church on Sunday. Lalor had “no choice but to learn to play music.” He chose the clarinet and violin as his instruments. His mother was from a medical family in the parish of St. Mary and had attended St. Hilda’s High School.
A Comfortable Childhood
Lalor’s childhood was quite comfortable,, and his father was involved in horse racing. As a result, at an early age, he and his brother were allowed to ride racehorses. He even obtained an amateur jockey license which enabled him to ride with the professionals at the Knutsford Park racetrack in Kingston. People would be surprised to know that his family once lived at 18 Retirement Road in West Kingston.
During WWII, Lalor's father would purchase the damaged cargo of ships that had been attacked by German U boats in the Caribbean. He remembers that they would hang soaked clothing and other materials to dry in their backyard and found there was a market for the slightly damaged items since at that time everything was in short supply.
Kingston College
He attended Kingston College Prep school when he was about eight years old and later Kingston College, an all-boys high school which his brother, Gerald, had attended a few years earlier. The curriculum was typical of the British grammar school and included religious instruction in accordance with the teachings of the Church of England. At Kingston College, he represented the school in track as a half-mile runner. He completed the Senior Cambridge exams before leaving after form 6B.
Lalor attended Kingston College from 1944 to 1952 and with a solid Kingston College education, he went forth to conquer the world of work.
Career Choice
After leaving Kingston College, Lalor worked in the civil service briefly before accepting a job in the general insurance industry with an agency, Lister Mair (Insurance) Ltd, agent for a UK company, Contingency Insurance. According to Lalor, he had “visions of studying medicine” as he and his brother were scientifically inclined but when his boss showed him a handbook with the salaries of every civil servant in the government and he realized what his salary would be after seven years of study, he began having second thoughts.
His boss explained that up to that time, no Jamaican had ever been certified as an insurance professional by the Chartered Insurance Institute in England. The company offered to pay for courses so he could begin the certification process. At this point, he was making five pounds per week in salary, and they offered to double his salary for each of three levels of certification he completed successfully. At that moment, “All thoughts of medicine left me,” recalls Lalor with a smile. By the time he completed the certifications, he was one of the first two certified insurers in the entire Caribbean. Today, he is very thankful for the guidance he received that got him started on an insurance career.
Recognizing Opportunity
Lalor moved up in the company rapidly and by 1956 he was the manager and director of the agency. When Lister Mair died in 1963, Lalor wondered if the business could be bought. Up until then, he had been quite content to continue working as an employee. He approached a friend he knew in a bank to see if he could finance a buyout. His friend who had attended Wolmer’s Boys School and whom he knew from playing football, approved immediately. Armed with a virtually blank check from the bank, Lalor went to England to wrap up the deal. By this time, he was the person in the agency with the know-how, and the folks in London recognized him as such. He subsequently took control of the agency which he renamed Dennis Lalor (Insurance) Ltd.
Jamaicanization of the Insurance Industry
Prior to Jamaica’s independence from Britain in 1962, most insurance companies operating on the island were merely agents of British companies. Upon gaining independence, Jamaica was brimming with optimism. A Jamaican, Carole Joan Crawford, had won the coveted Miss World title in London. The national airline was established. Enterprising Jamaicans felt empowered to soar to new heights. Remnants of colonialism were being dismantled at a rapid pace.
The Jamaica Association of General Insurance Companies, an association of general insurers, was formed in 1963 to address the interests and concerns of general insurers in Jamaica.
Lalor’s agency was sending 70% of all premiums collected to England while retaining 30% as commission. According to Lalor, “In the euphoria of independence, I asked why I am sending all this money to England?” Once more, he journeyed to London, but this time he asked them if they were willing to be part of a Jamaican insurance company—they declined but agreed to provide reinsurance for the new company. There were three giants of insurance in Jamaica at that time, and he felt he could compete with them.
The Insurance Company of the West Indies
In 1968, the Insurance Company of the West Indies (ICWI) came into being. Lalor was able to recruit several investors who collectively put up approximately £250,000 in capital. He retained controlling interest with 51% of the company and stipulated that no dividends would be issued for the first 10 years of the company’s existence.
Jamaica’s economic environment was booming in the 1960’s, recalls Lalor. “One pound was the equivalent of two US dollars and later one US dollar could be bought for something like 90 cents Jamaican… our economy was the model for the developing world.” Led by Alexander Bustamante, Jamaica had rejected the West Indies Federation and sought independence from England. According to Lalor, Bustamante had expressed the fear that poorer nations at the time, like Barbados and Trinidad & Tobago would have been a drag on Jamaica.
Growth by Acquisition
One early decision Lalor made was to expand by acquisition rather than fighting other companies in the Caribbean for business. Within 10 years, they had acquired the Insurance Company of Jamaica, Motor Owners Mutual and several British agencies operating on the island. One early innovation he championed was the creation of a separate policy for women drivers known as the “Road Angel.” Lalor realized that women drove about half as much as men and had far fewer accidents. It was an immediate hit. He made the first female bus driver in Jamaica—Dorothy Eubanks--the first policy holder. Soon every woman in Jamaica wanted to be a “Road Angel.”
ICWI then began to capitalize on its name and made several acquisitions in other Caribbean islands, which included brokerages and underwriting companies in Bahamas, Bermuda, Turks and Caicos, Trinidad & Tobago, St. Kitts and St. Maarten. They also bought a controlling interest in a life insurance company, Life of Jamaica (LOJ), which was later impacted by the meltdown in Jamaica’s financial sector in the 1990s. He got out of the life insurance business when LOJ was restructured and he was able to sell his interest. Lalor describes his foray into the life insurance sector as an “interesting adventure” but not a good fit for ICWI.
Insurance is Arithmetic
Lalor’s son, Paul, a Rhodes Scholar, joined him in the company after college and now handles most of the technical aspects of the business. Throughout the Caribbean, the company employs approximately 300 people. ICWI has 17 branches in Jamaica and usually employs several graduates from the University of the West Indies on a regular basis and puts them through a management training program. A perception and preference inventory helps them determine suitability for each type of job available.
According to Lalor, “Insurance is arithmetic. All you need to know is, of every dollar you collect, how much is going out in terms of claims… and you need to keep your eye on it every day. We get weekly statistics on accidents and claims. We analyze every claim with a fine-tooth comb… insurance is a risk business. But you have to prepare for it.” Hurricane Ivan, a category 5 storm in 2004, wiped out every insurance company in the Cayman Islands except for ICWI. ICWI is considered one of the best run non-life insurance companies in the Caribbean and has the most employees with insurance certification of any company in the Caribbean.
Improving Lives
Asked what the most gratifying aspect of his success has been, Lalor cites the fact that he has helped to develop so many people in Jamaica. He was also instrumental in improving the lives of the jockeys in Jamaica. Previously, as a group, jockeys were uneducated, very poor and without skills. When he served as chairman of the Gambling Commission and the Racing Commission, he created a school for the jockeys and implemented changes in the way they were compensated so that their salaries were managed by the commission which ensured that they were fairly treated.
A Dedication to Fairness
Fairness is a very important principle to Lalor and as he puts it, “if we could sum up my beliefs in one word it would be fairness.” For example, has always worked with governments of both political parties to serve the greater interests of Jamaica. He has instituted controls at ICWI so that no employee can be summarily dismissed without an appeal to the chairman being available to them, as long as they follow the established procedures. And whenever an employee decides to leave the company, he always gives them his blessing and tells them that, “if what they thought was green grass turns out to be white stone painted green,” they should not be afraid to call and ask if there is still a place for them. In fact, the company takes pride in the number of “returning residents” which is usually about 20% of staff.
Risks There Are
Several years ago, Lalor had an accident playing polo in which he broke his leg, femur, hip, and rib. He was taken off the field in a helicopter, and his condition was such that they were unable to operate on him for several weeks while he was in traction. After that he decided never to play polo again---Four years later he was back on the horse.
His advice to young entrepreneurs, “Don’t be afraid to take chances but in doing so be very careful, for risks there are; calculate how to mitigate them.”
A Life of Service
Throughout his career, Lalor has served Jamaica in a number of capacities unrelated to ICWI. The list is long but includes:
· Chairman of Freemasons Association (Jamaica) Limited
· Deputy Chairman of the Jamaica Association for the Deaf
· Chairman of the Lister Mair/Gilbey School for the Deaf
· Chairman, Betting, Gaming & Lotteries Commission
- Chairman of the Jamaica Racing Commission
- Management Committee of the Caribbean Council
- Fellow of the Jamaican Institute of Management
- Chairman of the University Development & Endowment Fund
- Member of the Privy Council of Jamaica
- Member of the Council of the University of the West Indies
- Member of the University Audit Committee
- President of the Private Sector Organization of Jamaica
· In 1993, in conjunction with the CARICOM Heads of State he formed the US$50 Million Caribbean Investment Fund.
· Chaired the High Advisory Council on Justice Reform in Jamaica
· 2008 - Board of Air Jamaica Limited and Chairman of the Privatization Committee
- 2010 -Chairman of the Air Jamaica Board
- 2011 - Director of Caribbean Airlines
- 2010 - Chairman of the Casino Gaming Commission.
He is a Board Member of several philanthropic organizations, including the Centre on Philanthropy & Civil Society (City University of New York) and served on the Board of the Council of the Washington based Council on Foundations and now serves in the capacity of Council Associate of the Board. He also served as a member of the International Board of United Way.
An accomplished polo player and former Captain of Jamaica Polo, he is also President of the Jamaica Polo Association and the Kingston Polo Club.
Awards
- Hall of Fame of Thoroughbred Racing
- Thoroughbred Breeders Regency Award
- Gleaner Special Award for Public Service
- Order of Jamaica
- 2006 Jamaica Observer Business Leader Award
- The Private Sector of Jamaica Hall of Fame
In 2008, he was the recipient of the Vice Chancellor’s Award and the UWI Alumni Association Pelican Award for contribution to the development of and dedicated service to the University of the West Indies.
Discussion
In 1994, he was the President of the Private Sector Organization of Jamaica—considered by many as the “pinnacle of business” in Jamaica (Johnson, 2008).
Lalor has been honored by the Jamaican government for his outstanding contributions to the country not only as a businessman but as a volunteer for the many services he has performed on behalf of the nation. He served as chairman of the national airline, Air Jamaica, as well as numerous other national organizations such as the Betting, Gaming & Lotteries Commission and the University Development & Endowment Fund. For this he received the national honor, order of Jamaica (OJ).
Lalor’s father had his own business as a merchant and wholesaler. Research has shown that entrepreneurs often come from homes where the mother or father was self-employed
(Crant, 1996; Dyer, 1992; Roberts and Wainer, 1968). Although Lalor did not set out to be an entrepreneur, he had the ability to recognize an opportunity when one was presented as he did by seeking certification in the insurance industry and buying the agency he worked for when the owner died.
Lalor is someone who is considered to have high self-efficacy. Self-efficacy is "the belief in one’s capabilities to organize and execute the courses of action required to manage prospective situations." In other words, self-efficacy is a person’s belief in his or her ability to succeed in a particular situation…” The most effective way of developing a strong sense of efficacy is through mastery experiences." Bandura described these beliefs as determinants of how people think, behave, and feel (Bandura, 1994).
Entrepreneurs take calculated risks. Insurance is concerned with risk management. For a fee, a person can transfer the risk of an event occurring to another party. Lalor knows how to appraise and control risk and is not afraid to take chances since he knows how to mitigate those risks.
The lessons from Lalor’s success include knowing how to recognize opportunity and the importance of having a solid education that prepares you to continue learning in any subject area. Managing risk is another vital lesson, especially in the insurance industry where this is crucial.
We also see the importance of social capital in Lalor’s story. Schmid and Robison (1995) demonstrated how social capital affects the probability of receiving a loan, the sale price of assets, and the willingness to share risk in their experiments to investigate the role of social capital in various transactions.
Entrepreneurs need financial capital to be successful, but they also need social capital. According to Adler and Kwon (2002), the goodwill that others have toward us is a valuable resource. They define social capital as “the goodwill available to individuals or groups.” Its source lies in the structure and content of the actor’s social relations. Its effects flow from the information, influence, and solidarity it makes available to the actor” (Adler and Kwon, 2002).
Dr. Glen Laman interviewed Dennis Lalor at his office in Kingston in 2013.