The late iconic Jamaican reggae singer Jimmy Cliff must have been a major favorite among the who’s who within the highest echelons of Cricket West Indies (CWI). In particular, among the likes of his fellow Jamaican countryman, CWI’s not that long ago appointed CEO Chris Dehring, as well as its incumbent President Dr Kishore Shallow and Director of Cricket Miles Bascombe. As much can be garnered from that threesome’s most recent utterances and activities, which individually and collectively have left many a West Indies cricket fan and follower with far “more questions than answers” regarding CWI’s ongoing management of the Caribbean region’s most popular sport.
As to whether cricket is actually still the region’s most popular sport, that may indeed be highly debatable. Especially against the increasing popularity of football and even more so the recent 2026 FIFA World Cup qualification attempts by Jamaica’s Reggae Boys, among others. Which, in stark contrast to the continued failings of West Indies cricket teams in international tournaments, most recently the ICC T20 World Cup, provided much-welcomed pride to the entire region!
What’s, however, not debatable in any manner whatsoever is the reality that CWI’s management of West Indies cricket continues to be a major source of concern, anguish, and/or even outright anger among the sport’s most fervent followers. CWI’s restructuring of its annual Regional 4-Day Championship into an entirely, arguably most idiotically non-competitive, new format was the first of several controversial decisions made within the first three to four months of this 2026, no longer so new year!
That was quickly followed by CWI’s somewhat surprising announcement of its appointment of the previously tried, tested, and some would suggest not nearly as successful as desired Otis Gibson as its Fast Bowling Consultant. Finally, there has also been CWI’s windiescricket.com news announcement of having, along with NCL Canada, “advanced plans to formalize a strategic partnership focused on the development of the Global T20 tournament and its supporting ecosystem in North America and the Caribbean!”
Starting, last things first, with this most recent April 15 announcement, the first question that immediately comes to mind is why in God’s good name would CWI even be contemplating taking an ownership stake in a Global T20 tournament that has proven to be a dismal, money-draining pit, in each of its three yearly stagings to date since its 2018 launch. Is this the same CWI that just last month was citing a deficit amount to millions of dollars in its finances? And which furthermore has been forced to reduce the aforementioned Four Day Championship to a farcical caricature of its former structure.
Even more damning was CWI President Dr Kishore Shallow’s recent announcement that last year’s much heralded Breakout T20 League would most likely not be staged this year, As a direct result of the very same current dire financial circumstances!
So if we are to understand the April 15 announcement correctly, CWI, with one hand, has been reformatting and cancelling its own regional tournaments left, right, and center as a direct result of limited financial resources. Incredulously, however, the very same CWI is with its other free hand is now hell bent on entering into a potential ownership agreement for arguably the most dubious of all the countless T20 Leagues which now populate the annual international cricketing calendar.
What’s even more surprising, if not outright disrespectful, is that Cricket Canada, the sport’s governing body in Canada, as well as CWI’s fellow ICC member, was not quoted anywhere in the announcement. The only mention made of Cricket Canada is President Shallow’s highly pompous, somewhat depreciative comment that “it could very well be a defining moment for their cricket development!”
Seems like the CWI President cum St Vincent Member of Parliament, Minister of Tourism, now also professes to be an expert on the needs of Canadian Cricket. That with which until now he’s had zero direct involvement!
In the two Josephs, Alzarri and Shamar, along with the ever-improving, constantly impressive Jayden Seales, the West Indies now possesses a three-prong pace attack potentially similar to Australia’s vaunted, highly successful Pat Cummins, Josh Hazlewood, and Mitchell Starc trio. As such, CWI should now perhaps be commended rather than criticized for having announced the reappointment of Barbados-born Otis Gibson as its Bowling Consultant.
Gibson enjoyed many years of success in an identical role for England and had also previously served as West Indies’ Head Coach. Indeed, the controversy surrounding his appointment has more to do with the now seemingly uncertain future of the West Indies current Bowling Coach, Trinidadian Ravi Rampaul. No mention was made whatsoever of Rampaul’s status within the Gibson announcement. Leaving fans yet again with, as Jimmy Cliff would have sung, “more questions than answers!”
Unquestionably, however, the most seriously damning questions of late have been those surrounding CWI’s restructuring of its annual Four Day Championship. Player performances during which will reportedly serve as a major influencing criterion for selection to West Indies Test teams in their forthcoming Home Series against Sri Lanka in June, and Pakistan this coming August.
Under this year’s newly restructured format, the Championship will feature three concurrent three-match bilateral series. For which the six regional franchises Guyana, Barbados, Jamaica, Leewards. Trinidad and Tobago and the Windwards will be seeded 1-6 based on their final standings at the end of the 2025 edition of the tournament.
According to the tournament’s schedule, which has already commenced with matches played from April 12-15, it will be Guyana vs Windwards, Trinidad vs Leewards, and Barbados vs Jamaica in three successive sets of matches. The Guyana vs Windwards and Trinidad vs Leewards matches will be played in Antigua, while the Jamaicans will be at home to the Bajans for their three first round matches.
The winners of each bilateral contest will then be ranked first through third based on total points accumulated, with the top-ranked team advancing straight to the Grand Final. During the Playoff Round, the top-ranked team will take on the West Indies Academy to maintain match readiness, while the teams ranked second and third will oppose each other to determine the second finalist.
Based on the decided schedule, the Championship will this year feature twelve matches in total. Nine of which will be played in Antigua, with Jamaica hosting the other three. An admitted cost-effective measure that is designed to significantly reduce the Championship’s associated air transportation expenses. The question that requires an immediate answer, however, is as to the likely negative effects on the tournament’s competitiveness. How much value is there to be gleaned from Guyana playing weak Windwards, Trinidad opposing equally frail Leewards, and the ever-unpredictable Bajans taking on equally inconsistent Jamaica for three successive matches?
Not that much if the first round results are in any way indicative! Trinidad romped to a massive innings victory over the Leewards within three days, while Guyana was only somewhat less dominant in recovering from a minor first innings deficit to defeat the Windwards by 4 wickets. Only the Barbados-Jamaica fixture was suitably competitive, with the hosts Jamaica eventually prevailing to win by seven wickets late on the fourth and final day.
The question being asked by many West Indies cricket followers is as to whether both the Championship itself, s well as CWI’s reported dire finances, would not have been better served by a format which would have instead featured the six franchises divided into two zones. Each consisting of three participating teams playing against each other in a round robin format with the top two finishers from each zone progressing to the semi-final. To be followed by a Grand Final involving the two semi-final winners.
Zone 1 could have been played in Antigua and Zone 2 in Jamaica, with the subsequent semis and Grand Final to be held in Antigua. Nine matches in total, just three fewer than the current format, but far more to play for competitively. And likely with negligible effects on CWI’s financial bottom line.
In terms of financing, the other million-dollar question now being pondered by West Indies cricket fans is as to why this year’s Championship is bereft of a title sponsor. Wasn’t the acquisition of corporate sponsorship supposed to be one of the anticipated accomplishments of CWI’s wonder-boy financial guru, CEO Chris Dehring?
Dehring, in his self-defense, can cite that CWI’s sponsorship acquisition activities may have been hampered by Rupert Hunter’s untimely February 2026 resignation as its Chief Commercial Officer. Notwithstanding the mal effects of Hunter’s departure, CWI’s ongoing failure to attract required sponsorship from powerhouse regional corporations such as Republic Bank, the Massy Group of Companies, and even Exxon justifiably raises many question marks over the effectiveness of its marketing strategies.
What was it that Jimmy Cliff sang again? More Questions Than Answers! Decidedly so!