Orrin Tonsingh: Jamaican Chess Legend

Jamaica Jamaica Jamaica

Approximately a month ago, Delise O’Meally contacted The Chess Drum’s Daaim Shabazz about Jamaican chess legend, Orrin Tonsingh. Tonsingh was one of the most prominent trailblazers in Jamaican chess and represented the nation on numerous occasions.

It turns out that O’Meally is the younger sister of Tonsingh and she wanted to share fond memories of her older brother. O’Meally is based in Indianapolis, USA and serves as an attorney for the National Collegiate Athletic Association (NCAA) where she is the Director of Governance and International Affairs.

O’Meally followed her brother’s footsteps into the field of law. In fact, it was a fire at the law office that claimed the life of her brother. O’Meally writes a very touching essay which is presented below. Enjoy!

Orrin Tonsingh: Jamaican Chess Legend
by Delise O’Meally

Orrin Tinsingh

Orrin Kerman Crarey Tonsingh was born on October 31, 1957 in Kingston, Jamaica. His mother (my mom) was Olga Winnifred Crarey, and his father was Oscar Kerman Tonsingh. He has 3 sisters, an older sister on his father’s side – Annette Tonsingh, and two younger sisters on his mother’s side – Yvette and Delise. [Yvette is an engineer at Microsoft Corporation in Seattle, Washington and Delise followed Orrin’s footsteps, and is an attorney working for the National Collegiate Athletic Association in Indianapolis, Indiana.] Orrin preceded both of his parents in death. His father passed away two years after Orrin died (in 1995) and his mother passed away in 2010.

Orrin Tonsingh with mother, Olga Winnifred Crarey. Photo courtesy of Delise O’Meally.

At about one year old Orrin developed asthma, an illness that was prevalent on his father’s side of the family. Doctors predicted that he would outgrow this but he never did and it is possible that his asthma made him more susceptible to the effects of smoke inhalation and contributed to his death on July 30, 1993. As a child he struggled with this condition, with many late night visits to the hospital for medication to overcome asthma attacks.

He started preschool at 3 years old. His first school was the Christian Day Prep School for boys on Oxford Road in Kingston. He did well in school despite missing 3-5 weeks each term due to his asthma attacks.

Orrin’s father was not involved in his life during his early years, in fact he saw him no more than a handful of times between birth and the age of 15. He was raised by his then single mother, his maternal grandparents Robert and Hilda Crarey and several of his aunts (mother’s sisters) contributed to his development.

Orrin and his mother moved to a more rural part of Jamaica when he was about 6, and he was sent to boarding school in Clarendon – Knox College. He struggled while in boarding school, lost lots of weight and seemed to have more episodes of asthma so his mother made the decision to remove him from the school, and send him back to Kingston to live with her parents while she continued to try to make a living on the western end of the island. She would travel to Kingston every other weekend to visit.

As is the rite of passage for all Jamaican school children, Orrin sat the Common Entrance Exam at around the age of 10, and earned a place in high school at Jamaica College High School in Kingston. After his first few weeks at school he requested his first Chess set. His mother found a small folding set in a bookstore and he was ecstatic. He learned the game fairly quickly. At heart he was an ardent sportsman although he couldn’t play football, cricket, or run track (the general sports of choice at the time) because of his asthma. He was a tremendous sports fan and did however keep scrapbooks of all sporting events.

Orrin Tinsingh playing with lawn set.

During this time in his life, he had several significant changes. His mother met and married my father, his grandmother, who had been his primary caregiver passed away from cancer, and he transferred high schools from Jamaica College to Cornwall College high school in Montego Bay. He remained at Cornwall College for the duration of his high school career. It was here that he blossomed as a chess player, competing in his first international tournament in Curacao in 1973, and leading his school to victory in the 1976 Schoolboy Chess Team Championships. Orrin passed his GCE External Exams in nine subjects with distinction and merit. After he took the Advanced level external exams, he sought and gained entry to the University of the West Indies in Cave Hill, Barbados where he began to pursue his goal of being an attorney.

Orrin Tinsingh playing Dr. Harold Chan.

During his teenage years and early college years, he connected with his father and his older sister, traveling to London with them. After he completed his degree at Cave Hill, he enrolled at the Norman Manley School of Law in Kingston Jamaica. Graduating as a full-fledged attorney at law and was admitted to the Bar. He started his practice with a group of attorneys and later branched out on his own.

He met his future wife Cheryl, while at Cave Hill, and married her in Antigua in August 1983. The couple had no children.

Chess remained his number one pastime. He excelled and was national champion more than once. He travelled to many countries to play chess and was able to observe the greatest Masters in the game. He earned a rating from the World Chess Federation and the title of National Master in 1983. He loved the game, two weeks before his untimely death he had indicated his intent to enter the national championships again.

Jamaican Olympiad team for 1990 Chess Olympiad in Novi Sad, Yugoslavia.

He passed away on July 30, 1993. He was at the Supreme Court on King Street in Kingston, from what I’ve heard he had just completed his case and was packing up to leave. According to the newspaper reports, at almost 2:00 in the afternoon there were several small explosions from the powerhouse and fire began, the electricity went out and the ground floor was engulfed in smoke. People ran out of the building, and Orrin did too but he was overcome by the smoke and collapsed upon making it outside the building. He was rushed to the hospital in the back of a police car but did not survive.

Jamaican Olympiad team for 1990 Chess Olympiad in Novi Sad, Yugoslavia.

I remember him as a soft spoken gentle person with a dry sense of humor, and an endearing chuckle. He was easy going in life, but strongly competitive academically and with chess. He was motivated to be successful and worked hard at all he did. From the eyes of a little sister, 11 years younger, he seemed like superman (and in fact claimed to be superman many times, or at least superman’s unassuming alter ego Clark Kent 🙂 The last time I saw him alive was while I was living in New York. He made a stop there on his way to a chess event in Europe. He, along with his good friend and chess colleague Neil Fairclough, spent a few days in New York around 1990. I miss most, the opportunity to have developed a deeper relationship as adults. He would be 54 this year.

Hope this helps…. Looking forward to reading what you write, thanks for keeping his memory alive.


National Anthem


  1. Selected Photos of Orrin Tonsingh

    Jamaica’s team at the opening ceremony of the 23rd World Students’ Chess Olympiad in Caracas, Venezuela, 7-22 August, 1976. From left: Bob Wheeler, John Powell (deceased), Peter Mundell, David Hunt (deceased), Enos Grant (Captain/delegate, deceased), Orrin Tonsingh (deceased), and Sheldon Wong. Photo from Jamaica Ambassadors Chess Academy.

    Orrin Tonsingh with close friend Neil Fairclough

    Orrin having a little fun! 🙂

  2. Thanks for sharing.
    Orrin passed away when I had just started tournament chess, I had met him once when I was purchasing my first tournament chess set (in 1993) from him.
    That last photo brings back so much memories because of the room its being played in.

      1. Its a room at College of Arts Science and Technology (CAST). CAST was renamed University of Technology (UTECH).

  3. Daaim,

    Many thanks for this. Tonsingh is a great part of Jamaica’s chess legacy, and has positvely impacted the development of many Jamaican chess players, including myself — from the context of both a chess administrator (it was he who gave me my first chess trophy back in 1992, I think) and a player.

    He unfortunately passed away not long after I hit the chess scene in Jamaica, but as an aspiring and budding chess junior then, he was one of the Masters I looked up to. I recall going through one of his games from the Manila Olympiad — a white side of a Sicilian Dragon — in a Jamaican Chess News Flash from 1992 and was very impressed by his play (The game can be found at https://www.365chess.com/game.php?gid=1973705 ).


    PS: The penultimate picture above shows Orrin with Neil (and not Kevin Brown). I have a picture with Orrin in it, which I will send to your mailbox and you could add it if you wish.

    1. Thank you Duane! I have made the correction. Please send any photos since there will add another piece to his legacy. His sister would also like to see these momentos. Send to webmaster@thechessdrum.net.

      Note: The conference was postponed (due to the unstability in the region) so I didn’t make it to the UAE. It would have been nice to visit with you in Oman.

  4. An extremely important legend in Jamaican chess!

    I recall getting newsletters in Montego Bay when I was just making grounds in this wonderful chess world… They would be littered with inspiring games and articles from Orrin. It was in this very city that we met at a Jamaica Open. Of course Micheal Siva (an important chess player, columnist and administrator in Montego Bay) had many stories of his friend Orrin as they also went to school together. It was always a joy to see Siva tell Orrin of my ‘so called’ talents.

    The attachments are numerous, including the fact that he went to my past high school Cornwall College and that his Sveshnikov games were so inspiring that it made my introduction to that opening very easy….

    Keep these coming Daaim, the nostalgia serves to keep us inspired and remind us what this game can mean…


  5. Winston Powell (Orrin’s Cousin) News of Orrin’s sudden death was first broadcast by news media in Jamaica at 5:00 PM. My Mother, her Sister, and I, arrived at Orrin’s home at 5:30 PM, to offer support to his wife Sheryl. Between 5:30 PM and 8:30 PM, the home was bombarded with so many telephone calls and personal visits from, mostly members of the Chess playing fraternity in Jamaica, that Orrin’s wife asked me to monitor the calls and visits, so she could have, at least the first couple of hours, to grieve in privte. I will always remember a teenaged Chess player who arrived at Orrin’s home, ( tears steaming down his face,) to express his condolences!!! Such was the esteem in which Orrin was held by Jamaica’s Chess playing community.

  6. I read this article with great happiness and also sorrow. Happiness as the legacy of NM Tonsign is being remembered in Chess history and the sorrow as I still miss my first Chess Mentor and coach.

    During the 1980’s and 1990’s Mr. Tonsign contributed significantly to the development of Junior chess, both by organising tournaments and helping to develop the young up and coming players. The Junior Ladder League was even named after him.

    Mr. Tonsign was intrumental in my first national Championship victory in 1992 as he spent countless nights teaching me his two favourite defenses the Kings Indian Defense and the Sveshnikov which still remain in my rep 20 years after in tribute to him.

    Daaim i thank you in assisting in ensuring that chess history remembers one of the greatest Jamaican chess players who has contributed significantly to Jamaican chess and to whom I owe a great deal of gratitude.

    Thank you
    Jomo Pitterson

    1. At the Manila chess olympiad in 1992 when Mauritius played Jamaica, i sat across the board to play Fairclough and my team-mate Chinasamy faced Tonsingh.After the game my team-mate told me he got a chess lesson in the KID from the bearded Tonsingh.We did not even know that he passed away the next year.By a strange twist of fate 18 years later the same Chinasamy played against Jomo Pitterson at the Khanty Mansisk olympiad

  7. Thank you for sharing these great memories with us.
    Orrin Tonsingh was god sent.
    He was instrumental in my development as a chess player.
    He was my voluntary coach and advisor in both Olympiads that I played with him.
    He would also lend me books and suggest openings to strengthen my game.
    Orrin was also always the first person to offer me a place to stay for the tournaments, since I traveled all the way from Westmoreland.
    It was a sad day when I heard of his passing.
    I would look to play in a tournament in Jamaica named “ THE ORRIN TONSINGH INTERNATIONAL “.

  8. Thanks to Devlin I heard about this more than well deserved tribute to Orrin Tonsingh. I truly miss him and was deeply saddened when I heard of his passing on the news. He was definitely a positive influence to the Palmers in the arena of chess. I looked up to him not just as a chess player but also an organizer. He appointed me to assist him on the JCF committee while I was still in high school that opened me up to his behind scene work and dedication to the sport. I didn’t know him as someone with a whole lot of words merely because his actions spoke a whole lot louder to me. He treated persons young and old with respect. He was a kind hearted man – many times he would offer to take me and/or my siblings (and other players without a ride) home after a committee meeting or a weekend match when possible.
    Tonsingh’s life was relatively short but very impactful – unforgettable. May God continue to comfort and strengthen his family and loved ones.

  9. A great chess and human interest story of an important era in Jamaican chess history. Well done.

  10. I am Orrin’s other sister mentioned in the article giving an account of his life. I’m sharing a piece of previously unknown information about our father by way of vindicating the little contact he had with Orrin in his early childhood. When I heard that I had a baby brother, I went into irrational and hystically screaming. Just being 7 years old at the time, no one seemed to be able to understand it. Most of all, my grandmother could not understand it and both she and my father were so grieved by my intolerable screaming and crying that they stopped mentioning that I had a brother. As time went on I forgot about it. Then one afternoon, I came home to see Orrin standing with his mother and my mother; he was 15 years old. I was absolutely delighted; I do not know who initiated the meeting, but that was the first time I met my brother Orrin. It was difficult to bond; we made several attempts to become brother and sister. Our father tried very hard to make it work by traveling together and he was very interested in Orrin’s education to be a lawyer as well as his progress in chess. He was proud of his son, but the distance created by my early anti-social behaviour was never repaired. Orrin and I kept in touch during his days at Cave Hill, then drifted apart again. When I heard of his death just a few days after I spoke with him for the last time, I could not believe that I would never again have an opportunity to try to revive our relationship. It perhaps just wasn’t to be. To Orrin: We’ll meet again. With Love, Annette.

  11. I miss Orrin very much and think and speak of him often. Our family knew his dad before he and I were born. We met as competitors in high school and became very good friends without knowing of our families’ connection. He was a good and caring person.

  12. I saw Orrin during the World Youth Team Championships in Chicago in 1983 (I believe). We didn’t formally meet, but I remember him because of his beard. I was taking a special interest in the Bahamas, Jamaica and Botswana.

  13. Very Good Article, it brought back good chess memories. Just like John Powell he was kind to Me. He also sold me my first tournament chess set. I need to check my chess archives for stuff with him.

  14. Very good post. Informed myself on this great Jamaican who also happened to be a great chess player.

  15. The highlight of my chess days in the early 1980s was earning a draw with Orrin. He was hosting a chess tournament at Church Teacher’s College in Mandeville at the time.

  16. Orrin has surely been a contributor to my passion for the game! He was surely one of, if not “the” that made me feel like teaching the game to others! Was never about money with him.. did it with pure love!
    Remembered when I was at CAST(now Utech) and he had asked for a challenge, said the only way I’m going to play is if his Queen stays off the board… and I still lost!
    Your memories lives on Mr. Tonsingh

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