Kipling Douglas passes away at 86

Kipling Ernest Douglas, author and longtime judge and magistrate in the Cayman Islands, passed away in Jamaica Sunday at the age of 86.

Mr. Douglas had served in courts in Jamaica, Turks and Caicos, and the Cayman Islands. He was also known for his tennis playing, rally car driving and writing about his career and travels around the world.

On Wednesday morning, judges, magistrates, attorneys and court staff gathered to pay tribute to Mr. Douglas, who served as magistrate and then senior magistrate in the Summary Courts of the Cayman Islands from 1983 to 1993. He subsequently acted as a judge of the Grand Court until 2004.

Chief Justice Anthony Smellie presented a tribute to the life and career of Mr. Douglas, noting his service as Chief Justice of Turks and Caicos from 1993 until his retirement in 1996, and the nickname he earned as a magistrate in Hanover, Jamaica – “Clip-Wing Douglas” for the “short, firm but appropriate sentences he imposed.”

A Cayman Compass reporter recalls the name bestowed in Cayman – “Crippling Douglas,” also for his firm sentences.

Justice Douglas once presided over a Grand Court session in which people dissatisfied with the outcome of their Summary Court matter appealed to the higher court. One man, who had received a term of imprisonment, presented his case. Justice Douglas looked at him and said words to the effect, “You want me to reduce your sentence? I’m wondering if I should increase it.” The man in the dock turned and quickly made his way down the stairs to the safety of the courthouse cells.

Justice Douglas indicated he was marking that file, “Appeal withdrawn.”

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Mr. Smellie detailed what he called Mr. Douglas’s “long and admirably fruitful and productive life.”

Mr. Douglas, who was born in Jamaica in 1930 and attended the prestigious Wolmers Boys School in Kingston, started his professional life as a civil servant in Jamaica, where he worked for three years before going to England in 1951 to study journalism. He returned to Jamaica in 1954 and worked with the Daily Gleaner until 1956. He next served as editor of the West Indian Law Magazine and as assistant news editor at Radio Jamaica.

Justice Kipling Douglas in earlier years.

Mr. Douglas returned to England in 1957 and worked at the London City Council. He registered at Middle Temple to study law and was called to the bar in 1963.

“He had by that time been married to his wife, Leslie, for some four years and they and their first child, Mark, returned to Jamaica in 1964, where lawyer Douglas entered private practice,” Mr. Smellie said.

Over the next 20 years Mr. Douglas practiced law in Jamaica and was resident magistrate in a number of parishes. On May 1, 1983, he was appointed magistrate of the Cayman Islands Summary Court, and in 1988 as senior magistrate. While in that post, he was appointed from time to time to act as a judge of the Grand Court and on occasion served as acting chief justice in the absence of the Chief Justice, Sir John Summerfield.

He was appointed Chief Justice of Turks and Caicos in 1993 and served there until he retired in 1996.

“But as a consummate lawyer and judge, he was not given to full retirement, and so from time to time accepted appointments as acting judge of the Grand Court until 2004, when he finally left judicial life to accept an appointment as legal advisor to the newly established Financial Reporting Authority within the Attorney General’s Office,” Mr. Smellie said.

“As a final crowning achievement of a long and distinguished career, a legal report carried this caption about Justice Douglas in June 2011: ‘Legal Heavyweight Leads New Cayman Firm,” Mr. Smellie quoted. He was referring to the retired judge’s appointment, with attorney Janet Francis, to head SmeetsLaw (Cayman), a member of the GCA Smeets Law network of independently run firms in the Caribbean, Latin America and Europe.

Mr. Douglas himself apparently considered that his crowning achievement within the legal fraternity was his election to the Executive Council of the Commonwealth Magistrates and Judges Association in 1985, where he served until 2016. He served this organization as regional vice president and then president from 1994-97, when he was made an honorary life vice president.

Combining his early career as journalist with his judicial life, Justice Douglas wrote “The Courtroom, the Poor Man’s Theatre,” in which he shared a collection of anecdotes from his 37 years in the courtroom.

Many remember Mr. Douglas for his travel articles published in local media [including the Compass and its sister publication The Sunday Observer].

Mr. Smellie said Justice Douglas would be remembered most fondly “for his insightfulness, his wonderful wit and sense of humor and all in all, as a very fine gentleman.”

Attorney General Samuel Bulgin said he had many fond memories of Mr. Douglas as a legal adviser. Having appeared before him in Magistrate’s Court, Mr. Bulgin could attest to his ability to mix common sense with the standards of the law, calling him “street smart.”

Attorney Neil Timms, an officer of the Caymanian Bar Association, said Cayman will miss “a gentleman of elegance and courtesy.” In many ways, Mr. Timms said, Mr. Douglas was “the incorruptible judge.”

Mr. Douglas, who would have observed his 87th birthday on June 24, is survived by wife Leslie, son Mark, daughter Elizabeth, and granddaughter Alhena, as well as brothers and sister.

Funeral services will be held at St. Andrew Parish Church in Kingston, Jamaica, on June 28 at 12:30 p.m.


  1. I used to really enjoy reading his travel articles in the Compass, and would often meet him in the lobby of Scotiabank when he would always spare the time for a friendly chat. Mr Smellie had it just right when calling him “all in all, a very fine gentleman”. He will be sadly missed by his family and friends.

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