Trinidad and Tobago international forward Jamille Boatswain’s whirlwind move to the Costa Rica First Division lasted just four months.
The former St Benedict’s College student and Defence Force and Point Fortin Civic poacher is on the lookout for a new opportunity after LD Alajuelense cut him from their roster today.

(Copyright LDA.cr)
Boatswain, who signed a two-year contract with the renowned Costa Rican club in late June 2017, was one of eight players offloaded by Alajuelense today. Costa Rica’s football season is split in two with an opening and closing season and Boatswain was deemed surplus to requirements for the latter half of the club’s schedule.
In his four months with Alajuelense, Boatswain managed two starts and six appearances with one goal.
However, he struggled to get playing time once Benito Floro, the coach who signed him, was replaced as head coach by former club hero, Wílmer López, in August. And the club activated a termination clause in his contract.
Boatswain’s agent, Sergi Roca, felt it was better that the 24-year-old found a team where he had a better chance of playing and insisted that, within hours of his release, there were other teams enquiring about his availability.
Roca, who is from Spain, said the player has enjoyed his time in Costa Rica so far and would prefer to find another club there.
“I think he will get a second chance but I am first in conversation with Costa Rica because he likes the country,” Roca told Wired868. “Jamille’s experience was productive for his career and now he is open to new challenges to continue growing as a player.”

Costa Rica won 2-1.
(Courtesy Allan V Crane/CA Images/Wired868)
Boatswain was one of a handful of Trinidad and Tobago players to head to Latin America in 2017, along with players like Daneil Cyrus, Jan-Michael Williams (both Honduras), Leston Paul (El Salvador) and Darren “Chucky” Mitchell (Guatemala).
Compatriots Jerrel Britto (Honduras), Dwane James (El Salvador), Jomal Williams and Shahdon Winchester (both Mexico) were already there while also on the radar of Central American clubs were a host of other players such as Curtis Gonzales, Hashim Arcia (both Defence Force), Nathan Lewis (San Juan Jabloteh), Sean De Silva, Jason Marcano (both Central FC) and Neil Benjamin Jr (W Connection).
W Connection and St Lucia international Kurt Frederick is at Alajuelense at present.
“Central American clubs have turned their backs on the Caribbean for decades [and were] obsessed with signing amateur South American players for large amounts of money,” said Roca. “Clubs are maturing, moving from a fetish attitude to a realistic attitude. The Caribbean is within reach and is a natural catchment area for continental teams.
“These leagues of intermediate level represent the ideal step in the development of a Caribbean player to its maximum level. If they succeed in Central America, the next step is Europe, Mexico or MLS.

(Courtesy Chevaughn Christopher/Wired868)
“Here, they can be seen by clubs from all over the world, since they are fully professionalized leagues where it is very easy to get videos, something vital nowadays.”
Apart from Boatswain, Roca manages Britto, Cyrus, Williams, Mitchell and Frederick. But he admits it has been a mixed bag for the regional players.
Moving from playing in front of mostly empty stadiums in Trinidad to the pressure of playing in front of thousands of demanding supporters in Central America constitutes a big change. And, as Boatswain also discovered, there is often little time to settle in since clubs expect a return on their investment almost immediately.
At present, Cyrus is one of the first names on the Juticalpa team sheet in Honduras while Britto is a genuine star at Honduras Progreso and James and Paul are also doing well at CD Pasaquina in El Salvador.
But, after an encouraging start, Williams has lost his place between the uprights at Juticalpa while Mitchell—at CD Guastatoya in Guatemala—and Frederick have been inconsistent.

USA won 2-0.
(Courtesy Allan V Crane/CA Images/Wired868)
Italian Simone Ghirlanda, another European agent with a sizeable stable of Trinidad and Tobago players, said it is risky to place young men into challenging environments before they are ready.
“I think it’s not a good practice to push unexperienced players into a situation like that of Boatswain in Alajuelense,” Ghirlanda told Wired868. “If Aubrey David had opened a door [with his performances at Deportivo Saprissa] in Costa Rica, this situation has closed it and it will be a long time before a Costa Rican club will take a chance on another T&T player.”
Roca and Boatswain may beg to differ but Ghirlanda, who is based in USA, says he was burnt to learn.
Almost two years ago, he engineered a move for Trinidad and Tobago forward Willis Plaza to top El Salvador team Alianza but it proved to be a disaster for all concerned.
Ghirlanda suggested that Plaza made a timid start to his life there and was never able to recover.
“If you don’t hit the ground running, the fans can be brutal,” said Ghirlanda. “In the MLS, fans go home and think about the rest of their lives but that is not the case in Central America. You are under the magnifying lens and if you are a striker or a defender, it is harder to hide because your mistakes count.”

(Copyright AFP 2017/Bienvenido Velasco)
In a few months, Alianza fans were booing whenever Plaza’s name was mentioned in the first team and he left before his contract expired.
It is important, Rico and Ghirlanda stressed, for Trinidad and Tobago players to understand the challenge facing them before they land in Latin America.
Most teams pay between US$1,200 and US$2,500 per month with modest accommodation provided by the clubs—although Plaza was on roughly US$4,000 per month at Alianza and Boatswain was probably paid somewhere in between the lowest and highest sum.
Ten years ago, Pro League clubs offered better salary packages than that. At present, though, Pro League players are often paid less—if at all—and there is no shortage of locals who are willing to travel for that figure, which is considered a good wage in many Latin American countries.
Many coaches in that part of the world are prejudiced against Caribbean players or don’t want the hassle of having a translator in their dressing room. Then the Warriors must also adapt to the food and the different training methods.

(Courtesy Allan V Crane/CONCACAF)
Sometimes, salaries are late too while you might be stuck in an apartment with no air-conditioning and in sweltering heat.
The Caribbean players generally enjoy it, though.
“Most of them like the [game day atmosphere] because it is more exciting to play in front of enthusiastic fans there than in front of just family and kids in the [United States lower leagues] or empty grounds in the Pro League,” said Ghirlanda. “They enjoy the roughness of the league too. People care about their football in Latin America and your name is in the press all the time and you are the centre of attention.
“They like that stuff.”
Gradually, the tide of opinion is changing among Latin American coaches too, who are being seduced by the athleticism of Caribbean players and like the idea of having an international in their first team.
Britto has helped and his story is an encouraging one for Boatswain. The former Queen’s Royal College student and Jabloteh and Connection player was also released within six months of sealing his first deal in Guatemala with Malacateco, which was also arranged by Ghirlanda.

Looking on is Connection assistant coach Earl Jean.
(Courtesy Allan V Crane/Wired868)
He did a bit better in the Mexico Third Division with Murcielagos FC. But the third time was the charm for the versatile frontman, as he helped Progreso to the Honduran final last season and was in the shortlist for the league’s MVP award.
It was Britto’s performances that cleared the way for Cyrus and Williams to sign with Honduran teams in the pre-season.
Britto’s first Central American employers, Malacateco, might not be in the market for another Trinidad and Tobago player anytime soon, though.
Last month, FIFA ordered the Guatemalan club to pay W Connection US$120,000 in training compensation for Britto—although the player moved there at 23, spent barely six months and left without Malacateco getting a transfer fee.
By FIFA law, training compensation can be demanded until the end of the season of a player’s 23rd birthday. Britto turned 23 on 4 July and the Guatemalan domestic calendar starts on 1 July.

Infantino was the UEFA general secretary at the time.
(Courtesy TTFA Media)
W Connection owner and Trinidad and Tobago Football Association (TTFA) president David John-Williams is a current member of the FIFA Players’ Status Committee, which ruled on the dispute.
“Malacateco are holding fund-raising events with fans to try to raise the money because they are at risk of losing their professional status,” said Ghirlanda. “That is a lot of money for clubs in that part of the world. Many teams in Guatemala will no longer touch players under 24 years old, especially from the Caribbean.
“[…] I do think it is very immoral for W Connection to ask a poor club in Guatemala to pay for a player whose level, as we know, is similar to hundreds of players which are regularly traded for free in the region.”
Boatswain’s own first professional deal ended without recrimination; a statement on the Alajuelense website thanked the players for their efforts and wished them success in their next projects.
Boatswain returns to Trinidad next week to join the Warriors for international friendly outings against Grenada and Guyana on 11 and 14 November respectively at the Ato Boldon Stadium in Couva.
No doubt, he will be hoping for an early return to Latin America.

Lasana Liburd is the managing director and chief editor at Wired868.com and a journalist with over 20 years experience at several Trinidad and Tobago and international publications including Play the Game, World Soccer, UK Guardian and the Trinidad Express.
LoL.
Exactly Nicholas. What happened to Beebo must never happen again. The board was too easy
Yes…I wrote for a pair of goal post nets & corner flags and couldn’t even get that as a donation. I wonder if any youth team was ever compensated? But I’m sure Allah has a saying for men who prosper on the affairs of others
Very insightfull reading. Was interesting to hear from an agent’s perspective. But thats the accountability that goes with being a pro. This doesnt apply to the pro league because its 50 people watching a game. Half of them on whatsapp or instagram most of the game. So who have time to boo a player when he unscores a goal or two? As coaches you try to apply reinforcement methods but the way you could dispose of players in these leagues you cant in trinidad. Then the whole idea of reinforcement is to get the player to do something or not do something FOR HIS OWN GOOD mind you and or that of the team. So therefore the player must CARE and see value in achieving the goal in mind if he doesnt as you say you can lead the horse to the water…..
But i always believed that the mexican league was a good place to start for our players. Ive even thought of mexican coaches for our national teams or at least our coaches going there and spending sometime to see how they do things there. The americans do it
Enjoyable article and informative comments! Must say I’m disappointed to read the last few lines….$120,000 US in training compensation 🙁
Thats not totally correct Nigel Myers. But i ask at what point does the players take resppnsibility for themselves? When men sneaking camp to party or playing minor before a WC qualifier ;should the coach/handler take the blame?
Dat is ah different kinda ting. I strictly talking bout going on a trial or going to take up your first contract or two.
Well me for sure. I does pong in my playerz head the importance of having that hunger drive and determination to succeed. How come the guys from the soca warriors era hold down contracts for yrs in europe??? Thats because in my day being a foreign based player was the thing to be. Now players cool with making a lil $4000 a mth in d pro league. Motivation to excel almost non existent.
Good question. I never really thought of it from that angle. Sometimes the drive is internal and sometimes it is transferred to you by a coach, mentor etc. The players from years gone by definitely fought for what they achieved. Nowadays players go on trial or contract and cry about the food, culture, weather, homesickness, you name it. Or they not aggressive in training, not leaving it all out on de pitch. And this is what I mean when I say they are not prepared properly. Not knowing what to expect, how to conduct themselves, how to give themselves the best chance of success etc. It takes way more than talent to make it out there.
Well bro as the old saying goes fail tp prepare prepare to fail. These guys todaycars very talented but the gang culture has seeped into every nook and cranny. By gang culture i mean what you wear,what you eat, what type of music you listen to etc etc all this come with a world owes me something mentallity , an ironic softness
Ancelotti reported this in Italy but it is common knowledge. When CR7 would get back along with the team with a charter flight from a match played in Champions League intra week and by the time they touched ground was often past midnight, most players would go straight home, he would go to the training centre at 1 am or so to immerge himself into iced water for 40 mins as it allows much faster recovery when you are playing every 3-4 days. And at home at the time he had Irina waiting for him. ?
HE DID NOT BECOME CR7 JUST BECAUSE OF TALENT, or some other random event like a coin flip, HE DID BECAUSE HE IS OBSESSIVE AT BEING THE BEST.
Self actualization
Dwight Yorke had a similar drive…I heard several stories from people in football and saw it myself when I would go to National Training sessions and watch him be the LAST to leave the field…and at that time he was the oldest member of the team…the players nowadays lack that kind of hunger and passion but hopefully Coaches like Travis will help groom the next generation from which our next Yorke will emerge.
I don’t know about you guys but I’m proud of Ovøxö Jamille Boatswain he reach further than most local footballers and he gained valuable experience… he’ll get back out there
U will be do better brother
Sincerely Hope it is not work ethics.
It was first highlighted by the German our national coach at that time when he expressed vuews in it that we not taking the time for our players to full develop for higher football we choise to rush them off to minnor keague football alk over the world he was under heavy attack for his statement
Lasana – this is an excellent informative article. Players who make the move to some of these Central America profession leagues need to understand that its important that they are successful. As their success creates opportunities for others. Brent – if you don’t have leverage it’s near impossible to get a guaranteed contract. A club would be mad to take such a risk on a player who is yet to establish himself. I wouldn’t call these shit contracts. They’re opportunities – stepping stones to bigger things. As Serena Willians told Venus Williams – if they take the opportunity more will come.
Los, I’m not saying he should be e gotten a 2 year deal or a guaranteed contract for that length of time. Simply saying don’t announce a 2 year deal when in fact it’s appears to be a month to month deal. I just hope the young man knew what he was signing.
Got yah. Agree that they need to be aware of what they’re signing. They’re got to read the fine prints.
In reality that’s the job of the agent…
Educate them Simone too many people living in the matrix
Thanks for taking time to answer some questions for us Simone. 😉
Great article
Well we have two big matches next week so hopefully they work in his favour somehow. ♀️
Plenty of top clubs scouts will be in attendance
Also worth noting that the top players at the top clubs in Central America or Mexico Ascenso can make as much as US$10,000 or more per month
I also don’t really understand the quote on the “amateur south american” players. Often those players come from second and third division Argentina, Brazil, Colombia, Uruguay, Chile, etc. Those are not amateur leagues. The TT Pro league is an amateur league.
The problem with most of these guys once they sign a contract the hunger and desire disappears
Agreed
If the contracts are so “shaky” then why would the hunger disappear?? That blows my mind NOW is when the work begins!! You get a chance to play and get paid for a game you’d play for free and now you lose the hunger??
Thank you Malik
In the case of Boatswain it wasn’t a lack of hunger. Things just didn’t go the right way for the team and the foreign players were not making a difference which is what they are there for. Given Central American clubs are limited to 4 foreigners, there is high pressure and they cannot simply be squad players.
Very good article, very informative.
Don’t forget that Dwane James was released by Guatemalan club, Antigua GFC, after only two months. And that was after Mekeil Williams had put in very good performances there.
For your info. I was finishing the season which was 4 months. Get your facts right bro.
Dwane, as far as I know, you signed a contract on February 2nd, 2016 which was for the rest of the 2015/16 season with an option to extend. The 2016 Torneo Clausura began on January 16th and ended on May 29th. Antigua GFC’s last match of the tournament was a 3-0 defeat to Malacateco on May 15th. Your last match was a 0-0 draw against Xelajú on March 9th, and you were released on April 4th, 2016. So you were there for basically two months. I am just stating the facts, not interpreting them. If I’m wrong about anything, feel free to correct me. My reference to you was just to show another instance where one of our players was released after a short amount of time. You did not let it discourage you, you persevered, and now you are a core part of CD Pasaquina.?
Yes Tallman, it seems that way. He was on a 2 year deal and cancelled it after 6 months? At least he should get paid
Hah. Brent we know MLS teams have those same contracts for many of their players.
Las, yuh saying he get cut and not getting paid? What clause could there be in the contract othet than the fact it’s not a two year guarantee?
The agent said so. Yes. And not unusual to me. I know plenty men who got the shaft just like that from MLS.
Shaka Hislop had a guaranteed contract and they had to pay him off. Most T&T players don’t get that.
Agents suck…. plain and simple. That and players desperate for a “outside contract”. Players either ignorant or being abused by agents
Shaka came to MLS as a high profile signing
Boatswain didn’t have much leverage. He had never even had a professional deal in his life. He was never going to turn that down, even with a release clause.
Don’t tell me it’s a 2 year deal and it can be terminated after 5 months with no compensation. That’s a stupid contract, plain and simple.
Brent it all depends on what terms are included., was it an incentive-laden contract? Performance based contingent on first team appearances? Everything is negotiable.
Exactly
Player being abused by agent? You have no idea what you are talking about buddy. I speak for myself but I make very very little money on moving players to Central America. Think about commissions of at times $500 for one year contract. I do it to see if the player can move up step by step which is why I think it is a bad idea to place players from the TT Pro league into any of the top 2-3 clubs in each country. They should start with smaller teams, where there is less pressure.
In El Salvador and Guatemala the release clause is mandated by the federation. It is one month salary and an additional month per tournament remaining on the contract. Hence why two year contracts for foreign players are almost never contemplated. This probably explains why Boatswain’s contract had an early release clause.
Thank you Simone people feel that agents are making millions when it’s always the players who reap the benefits while all we get as you said Is a small commission
Especially if it’s a small club and small league
Shit contract.. end of story. Agreed it can be incentive laden but still a shit contract…
“Shit contract?” Do you understand he was given an opportunity with a top team in Concacaf while having no experience at all and no history to show that he could make it there? Most players are having to start from the small clubs where conditions are bad in every sense including living conditions. Yes if you are a player in the TT Pro league you are by definition a player “desperate for an outside contract”
You made my point Simone, any player worth their salt not signing that deal. Players are clearly desperate and have little or no options. If that’s the case, we see what he signed.
You misunderstood my point. That is a huge option he had. Most clubs in USL require players to go on trial at their own dime. He had a straight contract without trial with a top club.
I respect your opinion as you’re speaking from experience Simone. It still doesn’t change the fact it’s a disappointing contract. It’s not a 2 year deal. Yes everything can be negotiated but 5 months? Clearly they scouted him and saw talent. Hopefully he gets another opportunity.
Brent its very difficult sometimes impossible to get a club to sign a player from Trinidad because we are not a football country so unless that player shows great ability a trial is always necessary
Who’s these fellas talkin bout shit contract? They’ve sent players to La Liga and Serie A? Got players in the CL making that cake? Steups. Let people talk yes.
Men have to understand that things not always gonna line up the way it is in your mind. Have a vision. Stick to it. Make the moves upwards.
A contract goes both way fellas it’s not a one way deal. It’s called negotiation.
Yeah but within the negotiations there’s leverage, which many poor unproven players lack. You then have to give up something in order to get something. Most of the times, as in this case, you give up the insistence on a guarantee in order to get the opportunity.
Agreed Nigel you aren’t negotiating from a position of strength. I’ve had some training in negotiations, I get it, but you should put provisions in place to get some kinda compensation should it not work out. I don’t know what’s in his contract so hopefully he did.
I don’t have any hard evidence, but anecdotally, it seems as though or players are typically not prepared properly by their handlers when heading to foreign lands for trials or to take up contracts. It seem as though dey does just send dem.
I feel you does be peeping in those practices sessions etc.
How your assumptions accurate so…..
Corbeaux sweat yes