Wired868 Wired868 for smart sport news and opinion
Unlike Cro Cro, Gypsy and Sugar Aloes, Dr Hollis “Chalkdust” Liverpool has spoken in 2026. But one wishes that, in this year of the 50th anniversary of his first Calypso Monarch crown, this indisputably influential personality had chosen to say more.
Everybody, I submit, would have won…
There is very little doubt that, with nine Calypso Monarch crowns now on his head, Chalkdust has a valid claim to being the Calypso King of the World. A statistical claim, no more.
(Copyright BuzzTT.)
Ditto Kitchener (11 Road March wins and a Monarch title) and now, a fortiori, Machel Montano (12 Road March wins, a Calypso Monarch title, seven Soca Monarch triumphs and a Chutney Soca victory.)
Even Bobby, a huge Kitchener fan, acknowledges Sparrow as Calypso’s Top Dog; eight Calypso Monarch crowns and the same number of Road March wins in the 36 years between 1956 and 1992 settles that issue.
Chalkie’s calypso credentials, however, are impeccable—no other current practitioner has so successfully married theory and practice. His five-decades odyssey on the calypso high seas, launched in 1967, finally landed him his ninth title in 2017.
Alas, in the Road March arena, his current tally remains at zero despite one notable 1983 up-tempo offering: Ash Wednesday Jail.
Photo: TUCO.
He spent over 30 years in the Trinidad and Tobago education system before becoming a cultural officer in the Ministry of Culture and then director of culture for six or seven years.
He now holds a master’s degree in History and a PhD in History and Ethnomusicology and is programme professor and lecturer in Carnival Studies at UTT.
If you wanted to be generous, you could also credit him with a share of the 2024 calypso crown, officially won by Machel, a graduate of the Calypso Studies programme masterminded by Chalkie. And he has authored half a dozen books on calypso and composed, he has said, well in excess of 300 calypsoes, which he calls ‘academic papers’.
But, despite all his undisputed calypso pluses, it’s not easy to be generous to a very self-conscious Chalkdust.
Didn’t he tell Mr Manning in 2007 to lock up kaisonians who sing about dawg and cyat? (That list includes even David Rudder. Check Hosay.) And recommend as well the erection of a Chalkdust statue in the Savannah?
Chalkie’s early stuff targeting politicians—Ah Fraid Karl, Ah Put on mih Guns again and Juba Dubai, for example, is really memorable. But when he turns his guns on his fellow calypsonians, one is often moved to switch off.
In the 80s and 90s, for instance, when Rudder was singing about calypso’s lyrics to make a politician cringe, Chalkie was singing Too Much Quacks. Within a decade, GB was telling us that Calypso Rising. Chalkie? Kaiso Sick in the Hospital.
This is a man who, as director of culture for a period straddling the first Manning and the first Basdeo Panday administrations, was well placed to exert real influence, at least on the context.
Now a record nine-time Calypso Monarch, he is just ‘Chalkdust’.
Notably, after his fifth win in 1993, Chalkdust’s next win came in 2004.
It might well be completely irrelevant but Gypsy’s only Calypso Monarch title, won with Little Black Boy, came in that period as did Black Stalin’s fifth and Cro Cro’s third. And in the ten years between 1994 and 2003, no fewer than eight first-time titleholders, including two women, were crowned.
One of them, Sugar Aloes would later refer, in his winning 2008 Reflections, to a Cro Cro claim that all dem judges were trained by Chalkie.
But when the allegators are the four-king king, Cro Cro, and the “disrespectful” Aloes, one can’t be certain what is mere picong and what is not.
When, anyway, in the run-up to Carnival 2026, Chalkie revealed that he had made TUCO an offer to train the judges, I could hardly wait to get the details.
I think it’s fair to observe that, where calypso judging is concerned, Chalkdust is not at all disinterested. In addition to his criticisms in song, he has made his views known in multiple interviews over the years.
“I offered myself to train the judges years ago and they told me that will be biased,” he immodestly told a Trinidad Guardian reporter, after the release of the names of the 2026 Dimanche Gras finalists. “So, if I can’t train them, who could train them?”
Challenging the selection of several of the 11 qualifiers, he suggested that judges need better education on “calypso structure and musicality”.
Photo: Tuco.
In an interview after his 2017 win, he had already identified three other pre-requisites for competent calypso judges:
#1. “You really can’t judge the artform if you haven’t sat down in a classroom for four, five months, six months.”
#2. Judges “have to know the difference between a simile and a metaphor, a hyperbole.”
#3 “They have to be literate, they have to know history. How could a man judge calypso and he has not even done Caribbean Civilization?”
Elsewhere, without identifying anyone in particular, he points to what, in his view, is a mistake some calypsonians make. He does not attack Indian people, he notes, he attacks people, Indian or African.
Photo: Newsday.
“I don’t sing about race,” he said, “I sing about events.”
One of his 2026 criticisms was a slap for the Calypso Fiesta judges and calypsonians alike—many of the offerings, including some that passed muster with the judges, were not true calypsoes but mere “freestyles”.
In the end, the master calypsonian disclosed that his offer had not been accepted. TUCO offered no public comment but questions arise.
With a view to saving the artform, was Chalkdust prepared to do the training free, gratis and for nothing? Or did the dean of calypsonians deem his services too valuable to be given away?
Photo: TUCO.
Was his price tag prohibitive? Was the offer a 2026 one-off or is it on the table for next year when, as seems possible, if not likely, TUCO will have new leadership?
With a view to saving the artform, could Chalkdust not have arranged to judge the competition as if he were on the adjudicating panel? Could he not have contrived to produce a set of results, complete with explanatory comments, thus allowing TUCO—and us all—to make a serious judgement of his claims?
Could he not have prepared and published for public scrutiny a telling commentary on the Dimanche Gras performances and results?
He did none of that. And so, we are none the wiser, no better placed to make the necessary judgement as to the quality of the judging.
Photo: NCC.
Alone in the foothills of the Northern Range this fo’daymorning, I was left with a distressing question unanswered: would a man genuinely interested in saving the artform not have gone the whole hog instead of offering us just a half-pick duck?
What will history remember about Carnival 2026? Not the mas, for sure! Post-Minshall, mas has been eminently forgettable. Most, especially Read more
Dogs, we have heard from since the Rock of Ages was a pebble, are man’s best friend. On the evidence Read more
Truth be told, Dr Keith Rowley should have held his tongue—he does not have the moral high ground. He should Read more
“[…] What is perhaps most instructive from the data on Trinidad and Tobago’s national culture is our incredibly low score Read more
“[…] Where is the music to ‘turn a woman’s body into jelly’? Where is the fun? The celebration? The ‘Spirit Read more
October and Calypso History Month are behind us now. February and Season 2026 beckon. What lies ahead? What is in Read more
Columns that say that, after Covid has done its worst, we’re grateful
to be still here and be able to get out of bed early to heed the poet’s
Carpe diem injunction and, savouring all the day’s blessings, mine
those banal, random, ordinary, routine, unspectacular, run-of-the-mill,
early-morning thoughts and conversations we often engage in.
