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Tobago youth determined to be successful even if that means moving to Trinidad.
Typography

SWO introduces Jaiye Sheppard - A Tobago bright-spark.

Jaiye was born February 16, 2002, to Clint and Asha Sheppard. From an infant growing up in Roxborough, Tobago, football was his primary love and he was nearly always seen with a ball except in situations where possessing a ball would be deemed inappropriate.

In 2011, when Jaiye was nine years old, he made his debut for the Roxborough Lakers U-13 team
in the newly formed National Youth League (NYL) Tobago Zone. That same year, he also participated in the Republic Cup U-13 competition.

The following year he again represented the Club but this time in the NYL U-14 competition. In 2013, the NYL folded, and the only competition available to Jaiye and other youth footballers in Tobago was a reformed Republic Cup competition which offered fewer games to participants. He played in this edition of the Cup with the Roxborough Lakers U-15 team.

Jaiye was conceding as much as 4 years to some of his teammates and opponents and a lot of size (he was quite small physically), yet he didn’t seem out of place.

Throughout this time, Jaiye also represented his school – St. Barnabas Anglican in the Tobago Primary Schools Competition.

To continue the development of the Lakers’ youth players, an elite team was formed, comprising the most promising players from the U-15 and U-17 teams with a few U-19 players. The only opportunities available were in the adult Village leagues.

The team made its first appearance in the Goodwood League in 2013. Jaiye didn’t make any appearances, as Lakers staff thought he was not quite ready.

In 2014, with his parents’ blessings, he played in all the games for the Lakers Development team and also played in the Georgia League that same year.

His time on the pitch and his responsibilities were geared towards helping him to navigate this new physically and technically challenging environment where he was now competing with players as much as three times his age. He relished it and began to display qualities of technical maturity.

The Roxborough-born, left-footed player was adjudged the “Most Promising Player” in the League, walking away with the trophy awarded to him at the end of the competition.

This experience certainly was good preparation for his next challenge to come. He was a first former at Scarborough Secondary School and was immediately drafted into the team's senior roster for the 2014 SSFL Tobago Zone season.

In 2015, he picked up where he left off. Brimming with confidence, familiarity with the League and a determination to make a bigger impression than he has made to date.

He took the Georgia League by storm and could very well have been the biggest “draw” at the League.

There was a concern about his ability to handle his increasing popularity with the local supporters. This
was soon dispelled as his focus was always on improving his performances and played to the “gallery” very infrequently. This time it was no surprise that he repeated as winner of the “Most Promising Player” Award.

Next, was the Tobago Screening for players born in 2000 and 2001 for selection to the Pool of
players from which the National U-15 T&T team would be selected from. He was encouraged to attend so that he would become familiar with the process of National team screening.

Never to be denied, Jaiye was one of five (5) Tobagonian players selected. Unfortunately for him, funding problems of the National Football governing body made it impossible for him to attend training sessions that were ongoing in Trinidad. Not for the first time the Tobagonians were denied the opportunity to stake their claims for inclusion in a National Sport team.

The year closed with some indifferent performances by his Scarborough Secondary School team – early favourites to cop the Tobago Zone Championship. They walked away empty handed.

Jaiye continuing his football education with lesson that came with the agony of the defeats that derailed their once promising season.

In 2016 it was much better as another screening session was held to select players for the National U-17 team. Jaiye was again successful.

They were now able to join the player from the previous year’s U-15 team who were training as a squad for more than a year.

He was making his mark, demonstrating his technical competence, while never shrinking from the physical battles that came with the territory.

He had a couple years of experience that he gained in the Georgia League and Tobago Zone SSFL that were serving him in good stead.

The coach of 1976 Phoenix FC came calling and persuaded Jaiye’s parents to have him join the ranks of the Super League Club.

However, more disappointment came and was lurking around the corner. This time the National coach was
dismissed and when training resumed under his replacement, the Tobago players were not invited. That team failed at the first hurdle.

And now 2017, more National team screenings. Nothing new here for Jaiye, right?

The format was changed though, 50 players were selected and Jaiye was among them as was expected. A new National U15 team, 2 years later, there he was with the U15s again. The story board was looking the same too.

Training was going on in Trinidad. The “Trini” players involved, but the Tobago players were not. Yes, more funding problems.

It was now Easter vacation, and with Jaiye’s parents smarting from the experience of 2015. They together with the other parents of the Tobago players that were invited, funded the travel for the youngsters to go to Trinidad to train with the National team.

Jaiye was selected, and was off to the Cayman Islands in May for his first International tour, representing Trinidad and Tobago U-15s at the Cayman Airways International Cup. He was now facing off against players from clubs like; Champions Manchester City and DC United.

Buoyed by his successes, his parents continued to fund his weekly trips to train with the National team – a truly noble sacrifice!

Jaiye was again selected to represent the National U-15 team in the Concacaf U-15 Tournament in Florida, USA during the first half of August. The team got eliminated, but the post-mortem revealed that Jaiye was the Trinidad and Tobago player that stood out at the tournament.

He then returned to Tobago and early enough that he would get a chance to represent his boyhood club Roxborough Lakers one more time, making his debut in the Tobago Football Association Premier Division.

He then transferred to Presentation College (San Fernando) for both sporting and academic reasons. He represented his new school in the just concluded SSFL Premier Division, winning the zone championship in 2018 and also winning the 2019 Intercol title.

Scoring 14 goals and providing a number of assists as well. He was instrumental in helping his new school claimed the Co­ca-Co­la South Zone In­ter­Col crown and its first-ever Na­tion­al In­ter­Col ti­tle. For his effort, he was also 2019 SSFL overall MVP.

In May 2019, Jaiye represented the T&T U-17 team that participated in the 2019 CONCACAF Men’s Championship in Florida. One notable standout was scoring a double over Caribbean-rivals Jamaica that stole a sweet 3-2 victory over the young Reggae Boyz and ensured that T&T did not finished last in the Tournament.

Bringing to conclusion another exciting year in his football journey. Jaiye has achieved quite a lot for his age already. The sobering thought is that he has only just begun to tap into his vast potential.

Some other Tobago-born players that stood out were: Adriel George and Keanu Boatswain, both are under the age of 18 and Kwame Mc Dougall of Stokely Vale FC.

Jaiye’s football biographical sketch

2011: Roxborough Lakers- National Youth League – Tobago Zone U-13 - Republic Cup U-13
St. Barnabas Anglican

2012: Roxborough Lakers- National Youth League – Tobago Zone U-14 St. Barnabas Anglican

2013: Roxborough Lakers- Republic Cup U-15 St. Barnabas Anglican

2014: Roxborough Lakers- Georgia League (Men) – Most Promising Player Scarborough
Secondary- SSFL Tobago Zone

2015: Roxborough Lakers- Georgia League (Men) – Most Promising Player Selected to
National U-15 Pool- Training
Scarborough Secondary- SSFL Tobago Zone

2016: 1976 Phoenix FC
TFA U-17 Youth Development Programme
Selected to National U-17 Pool- Training Scarborough Secondary- SSFL Tobago Zone

2017: National U-15 team – Cayman Airways International Cup – Cayman Islands - May --
Concacaf U-15 Tournament – Florida - August
Roxborough Lakers- Tobago Football Association Premier Division Presentation College,
San Fernando- SSFL Premier Division – Champions

2018: Presentation College, San Fernando- SSFL Premier Division - National U-16 Champions

2019: National U-17 team – Concacaf U-17 Championsip – Florida - May
Roxborough Lakers- Tobago Football Association Premier Division
Presentation College, San Fernando- SSFL Premier Division – Intercol Champions

2020: National U-20 Pool.

2020: Playing with Deportivo Point Fortin Youths - Next Lev­el Con­sult­ing (NLC) Lim­it­ed Un­der-19 Di­vi­sion Com­mu­ni­ty In­vi­ta­tion­al Foot­ball Tour­na­ment.