December, 31 1964 – Winston Keithroy Matthew Benjamin was born to Reynold Benjamin and
Agatha Matthew both of All Saints. 

His early education was at the All Saints Primary School, now known as the J.T. Ambrose
Primary School. He then attended the All Saints Secondary School and the Seventh-Day
Adventist Secondary School, which was located on the western side of St. John’s Anglican
Cathedral on Church Street.

Growing up, Benjamin recalls the strong discipline emphasized by his mother and her insistence
on spiritual development by always ensuring that the family attended church on a weekly basis
at the Tyrells Roman Catholic Church. 

Early in his life, Benjamin became interested in cricket as his father was also a cricketer. He
vividly recalls his father paying people to bowl balls at him as his father wanted him to become a
wicketkeeper. However, this trajectory soon changed for him after a ball hit him in the side by an
individual who bragged about it in school. Benjamin decided then that he needed to get back at
him but could not do so behind a wicket. This led to his training to become a bowler, as his
rationale was that ‘you can’t keep wicket and get people.’  He recounts that to date, he has not
had the opportunity to bowl to that individual; however, he is grateful for how things happened,
as it gave him a head start on a successful cricketing career. 

Benjamin’s cricketing foundation was at All Saints Secondary. He also played for the Buckleys
team in Parish League cricket, the All Saints Cricket team, and the Combined Schools in
domestic first-class cricket. 

Upon completing school in 1985, Sir Vivian Richards facilitated a scholarship for Winston to
attend the Chester Boughton Hall Cricket Club in Lancashire, England, an opportunity that came
quite by chance but would have a lasting impact on Benjamin’s cricketing career. 
He recalls one day, on his way to tend to his father’s animals, he saw a crowd gathered at
McPond in All Saints and ventured over to see what was happening. The people were all
gathered around to see Sir Viv in action. While sitting on his donkey, Benjamin muttered to
himself, “I can bowl at Sir Viv,” but he did not realize anyone had heard him. Before he knew it,
he stood ball in hand, ready to bowl. When he threw the ball, it hit Sir Viv on the hand; Benjamin
got scared and quickly rode away on his donkey. When he got home, his mother was at the gate
waiting, a position she would usually take up when he was in trouble. To his relief, she was only
waiting to share with him about Sir Viv’s visit and his offer of a cricket scholarship. Benjamin
was quite elated at this prospect to the disappointment of his mother, who wanted him to take a
scholarship to study computers in the United States as she was concerned that one injury could
mean the end of his cricketing career. 

Choosing to follow his passion, Benjamin accepted the scholarship to the English cricket club. During his tenure at the Chester Boughton Hall Cricket Club, he would represent in the
highly rated Liverpool Competition.  He finished the season with 106 wickets at an average of 7.57 per wicket, a best of 8 wickets for 20 runs, and collected 5 or more wickets 11 times, contributing to the club finishing the season as champions. His stint at Chester Boughton Hall improved his game and instilled the importance of punctuality and patience, all essential attributes for a solid cricketing career. He also benefited from all-around life skills development, learning to manage life independently, cooking and laundry, tasks his mom would have prepared him for in his formative years, and building a broader base on his socialization and networking skills.
He built on the successful start in England and caught the attention of other clubs in the County Championship. He was contracted to Leicestershire, where he played from 1986 to 1993, and then Hampshire from 1994 to 1996.

Benjamin reflects that this elevation in his cricketing status was bittersweet. His father, the main
reason behind his interest in the sport, passed just around the time he was due to return from a
second stint in England, playing with the Leicestershire County Cricket Club. Benjamin recalls
how he cried at the news of his father’s passing because he knew his father had high hopes for
him in the game and he would not get to see him play at the highest levels. 

Despite the setbacks, Benjamin would build on his Leeward Islands selection in early 1986 to go
on to debuts in One Day International (ODI) cricket against Pakistan on October 17, 1986, and
Test cricket against India from November 25 to 29, 1987, playing mainly as a right arm fast
bowler and a right-hand batsman. This would mark the start of a career that would span close to
8 years, allowing him to amass 1,648 runs and 61 wickets in test match cricket and 3,079 runs
and 100 wickets in ODI’s. 

Winston counts his most memorable game as the test match in Barbados against Pakistan in
the 1987-1988 season, where he was able to deliver in an impactful way to contribute towards a
crucial win that would have ranked Sir Viv as being the only West Indies captain to have never
lost a home series and ensuring that West Indies maintained their dominance of world cricket at
that time. Benjamin notes that he is grateful to Sir Viv for allowing him to expand his game and
knowledge of the game. He notes, “that opportunity propelled me forward and gave me that
platform to showcase my talent.” 

On April (29)1995, he played his final test match against Australia at Sabina Park, Jamaica, and
his last ODI at Lord’s in England on May 28 of the same year. Despite having the potential to
deliver even more at 29, Benjamin points out he was not pleased with things happening and
decided to leave the game with no official retirement announcement.
Following this, he went into coaching, which he enjoys because it allows him to work with
youth. 

He has worked with the Leeward Islands team and is currently a school cricket coach within the
Ministry of Sports, Government of Antigua and Barbuda. His passion for mentoring young
people in their development in the sport has led to his creation of the Grassroot Cricket
Academy, which welcomes youth from five years old. Some current cricketing talents who have
benefitted from his influence include West Indies fast bowler Alzarri Joseph, West Indies
Women’s bowler Shawnisha Hector, and Kadeem Henry, who recently debuted for the Leeward
Islands Hurricanes. 

Benjamin is quite pleased with his proteges’ accomplishments, which reflect the hard work they
have put in and signify the importance of his continuing that work.