Jamaica on The Tradewinds Brief

Cousin Leroy Explains Jamaica to His Coworkers at the Annual Performance Review

Wed, 22 Apr 2026 10:00:00 -0400

Cousin Leroy, a management consultant in the Bronx who has not visited Jamaica since 2019, is asked at his annual performance review whether he has any 'cultural perspective' to share about recent Caribbean news. Everyone regrets this.

Jamaica's Real Early Warning System Is Your Cousin's WhatsApp Group at 3 A.M.

Wed, 22 Apr 2026 09:00:00 -0400

A sardonic look at where Jamaicans actually go for weather updates, disaster alerts, and news that matters. Spoiler: it's not the Met Service.

The Remittance Corridor Breaks First: Why Sending Money to Jamaica During Disaster Season Doesn't Work the Way You Think

Wed, 22 Apr 2026 08:00:00 -0400

An evergreen look at the Jamaica remittance economy through the lens of what breaks during disaster season — and what that says about the diaspora-to-island money pipeline the rest of the year.

Aenon Town Cut Off as Clarendon Flooding Worsens, MP Calls for Emergency Drainage Audit

Wed, 22 Apr 2026 07:00:00 -0400

Residents stranded across multiple routes as Aenon Town floods for the second consecutive day. MP Wavel Hinds is pressing for a full drainage audit, and the backdrop is a post-Melissa infrastructure system that still hasn't recovered.

Cousin Leroy - Monday, April 20, 2026

Mon, 20 Apr 2026 08:15:00 -0400

Cousin Leroy reading the news from his apartment in the Bronx, where everything Jamaica is doing sounds, frankly, amazing — the recovery is going great, the casinos are happening, the Prime Minister flew to New York, and there's a $6.7 billion package coming, which Leroy is fairly sure is going to him personally.

Yard Report - Monday, April 20, 2026

Mon, 20 Apr 2026 08:00:00 -0400

Kingston view: ROOFS Programme is going at the speed of a man who has no banking app, the casino regulations finally arrived sixteen years after the law that needed them, and the Prime Minister explains that the unbanked are the bottleneck — which, accurate, but interesting choice of framing.

Cousin Leroy: Jamaica Pension Ting, Howard Lau Waste Bin Issue, and Why I Can't Even Believe What Is Going On Down There

Sun, 19 Apr 2026 11:30:00 -0400

Greetings from the Bronx. Cousin Leroy here. I have to tell you, I was on the phone with Cousin Pearl this morning — she still in Kingston, she don’t come to America, she say America too cold — and she read me the Gleaner front page, and I am sitting here in my apartment on 233rd Street and I cannot believe what I am hearing.

The pension ting

So Pearl tell me that retired police officers in Jamaica — people who serve thirty years — cannot pay their light bill because the pension system is not paying them out properly. Thirty years! Thirty years in the JCF! These men, some of them my age, some of them younger, they walking into retirement expecting to live on their pension, and the pension office telling them “late July 2026.”

Yard Report: The Pension Office Says 'Late July 2026,' Howard Lau Says 'Not My Bill,' and the Reggae Girlz Say 'Guyana, Hold My Coffee'

Sun, 19 Apr 2026 11:00:00 -0400

Kingston morning. Another Sunday of the Gleaner delivering exactly the news we knew was coming but hoped would not. Let us walk through it.

The pension scandal finally gets its Sunday front page

The Gleaner’s lead today is the story they have been building to for months. Retired police officers who served three decades cannot pay their light bills because the JCF pension system is broken. “Marlon Campbell” (pseudonym, smart) retired after over two decades in the force, left almost a decade ago, and is still waiting for his final pension letter. He is receiving an interim monthly pension of J$100,000 — the figure that precedes the final amount, the one you get while the paperwork grinds.

Caribbean Daily Brief: Jamaica's Pension Scandal Widens, Trinidad Finds 56 Bodies in a Cemetery (Not Buried), Barbados Gets Fitch Warning, and the Reggae Girlz-Golden Jaguars Match Is Tonight

Sun, 19 Apr 2026 10:00:00 -0400

Sunday across the region. The kind of Sunday where three countries produce three completely different species of chaos and we pretend this is normal. Pour your rum punch. Here is what is happening.

JAMAICA — The Pension Scandal Gets Worse

Retired police officers cannot pay their light bills

The Sunday Gleaner’s lead story this morning is devastating. Retired Jamaican police officers — some who served three decades — are unable to pay basic household bills because their pensions have never been properly processed. Retiree “Marlon Campbell” (pseudonym) told the paper he has been getting an interim monthly pension of just over J$100,000 for nearly a decade, still waiting for his final pension letter.

Cousin Leroy: Yo Dem REALLY Charge Jaii Frais??? And Somebody Stole De HURRICANE RELIEF?? From CANADA?? Yo WHAT

Sat, 18 Apr 2026 09:00:00 -0400

Yooooo wah gwaan fam. Leroy here calling from the BX on my 15-minute break at Logan, I am literally eating a bodega sandwich as I type this, and I have to put DOWN the sandwich because I JUST SAW THE JAMAICA NEWS.

Listen. LISTEN.

THEY CHARGED JAII FRAIS. THEY ACTUALLY CHARGED HIM.

Yo.

YO.

Remember yesterday when I told y’all they were holding Jaii Frais in custody and the judge had to tell them to charge or release him by 6PM? Well — THEY CHARGED HIM. Three charges. Wounding with intent. Shooting with intent. Possession of a prohibited weapon.

Yard Report: Dem Charge Jaii Frais, MSMEs in Triple Threat, Second Sibling Gone in Spanish Town, and a Canadian Man Steals De Hurricane Relief

Sat, 18 Apr 2026 08:30:00 -0400

Morning, Jamrock. Yard Report here on a Saturday morning, working through coffee and trying to reconcile the week’s news with the limited supply of patience I woke up with.

Let me walk you through what we have.

Jaii Frais Charged: “Survival” on Trial

Popular vlogger Jhaedee Richards — known to his large audience as Jaii Frais — has been charged. Wounding with intent. Shooting with intent. Possession of a prohibited weapon. The charges come six days after the shooting at the Big Wall carnival afterparty in St Andrew, during which Frais and two other men were injured.

Cousin Leroy: Yow, Dem Lock Up Jaii Frais? Wha' Gwaan Wid Dat! And Mi Nah Cosign Dem Find Oil in Yard

Fri, 17 Apr 2026 08:30:00 -0400

Yooooo wah gwaan fam it’s your cousin Leroy calling from the BX, 174th and Morris Avenue, shoutout to everybody at the spot on White Plains Road, and I just saw the news from yard and I had to hop on here before my shift at Logan start.

Listen.

THEY LOCK UP JAII FRAIS?????

I’m sorry — THEY WHAT?

Yo I been watching Jaii Frais content for LIKE two years now. The man is a VLOGGER. A VLOGGER. He go to parties, he put out content, he’s a MEDIA personality. How you gonna lock him up since Sunday because there was a SHOOTING at the party HE WAS A GUEST AT?

Yard Report: The Vlogger, the Mayor-Chopper, the Oil We Shouldn't Want, and the Trench Town Birthday Party That Turned Into a Crime Scene

Fri, 17 Apr 2026 08:00:00 -0400

Morning, Jamrock. Yard Report here from Kingston, processing the week the only way I know how — slowly, with black coffee, and with the grim understanding that the news will somehow get worse before I finish typing.

Let’s see what we’re working with today.

Jaii Frais: The Custody Clock Ticks Down

Popular vlogger Jaii Frais — real name Jhaedee Richards — has been in custody since Sunday following a shooting at the carnival after-party Big Wall. This morning, a Kingston and St Andrew Parish Court judge ruled that the police must either charge him or release him by 6 p.m. today.

Cousin Leroy Reports Back — Thursday, April 16, 2026

Thu, 16 Apr 2026 07:30:00 -0500

Leroy has been following the Westmoreland situation from the Bronx and has thoughts.

Yard Report — Thursday, April 16, 2026

Thu, 16 Apr 2026 07:00:00 -0500

Six months after Melissa, Westmoreland still dark. UHWI owes $40 billion in taxes. Carnival was nice though.

Cousin Leroy Report — Sunday, April 12, 2026

Sun, 12 Apr 2026 08:05:00 -0500

Cousin Leroy is watching Road March from the Bronx on his phone, upset about the Negril ambulance situation, and has opinions about the oil price and the budget.

Yard Report — Sunday, April 12, 2026

Sun, 12 Apr 2026 08:00:00 -0500

Road March Sunday in Kingston, Negril still has no ambulance, a Jamaican referee is going to the World Cup, and the budget's oil price assumption is looking embarrassing.

Cousin Leroy Report — Saturday, April 11, 2026

Sat, 11 Apr 2026 08:05:00 -0500

Cousin Leroy, calling in from the Bronx, has thoughts on Bunny Shaw's hat-trick, the Maryland plaque ceremony, and why he hasn't been back to Spanish Town in a while.

Yard Report — Saturday, April 11, 2026

Sat, 11 Apr 2026 08:00:00 -0500

Spanish Town mourns a teenager lost in a house fire, 71 dead on the roads already this year, and Bunny Shaw scores a hat-trick while the government hands out plaques in Maryland.

Jamaica Brief — Cousin Leroy, April 10, 2026

Fri, 10 Apr 2026 00:00:00 +0000

Leroy in the Bronx has thoughts about Shanoya, the soldier situation, gas station robberies, and why Jamaica keep making him proud and worried at the same time.

Jamaica Brief — Yard Report, April 10, 2026

Fri, 10 Apr 2026 00:00:00 +0000

JDF soldier charged with girlfriend's murder, bartender shot in St. Elizabeth, Shanoya Douglas has world leads, and an MP has been summoned. Another Friday in Jamaica.

Cousin Leroy's Jamaica Update – Thursday, April 9, 2026

Thu, 09 Apr 2026 00:00:00 +0000

Cousin Leroy in the Bronx reads the Jamaica news and has some thoughts.

The Yard Report – Thursday, April 9, 2026

Thu, 09 Apr 2026 00:00:00 +0000

Dispatches from Kingston — gas going up, hurricane victims still in schools, and Jamaica not in the World Cup. A normal week.

Caribbean Daily Brief – April 8, 2026

Wed, 08 Apr 2026 00:00:00 +0000

Your Wednesday Caribbean roundup: World Bank says slow down, Jamaica goes backward, T&T chases Venezuela gas, Barbados grows quietly, and Carifta children run fast.

Cousin Leroy's Jamaica Dispatch – April 8, 2026

Wed, 08 Apr 2026 00:00:00 +0000

Cousin Leroy in the Bronx shares his extremely confident take on Jamaica news. Economy, shelters, and why he still thinks JA is the greatest.

The Yard Report – April 8, 2026

Wed, 08 Apr 2026 00:00:00 +0000

Kingston's sardonic take on Jamaica's minus-one-percent growth, students exposed to sex in school shelters, and a JDF soldier charged with murder.

Caribbean Daily Brief — Tuesday, April 7, 2026

Tue, 07 Apr 2026 07:00:00 -0400

CARIFTA wraps in Grenada with Jamaica dominant. Trinidad declares another state of emergency. Barbados voter turnout hits historic low. The Caribbean in 5 minutes.

Caribbean Brief – Sunday, April 6, 2026

Mon, 06 Apr 2026 10:00:00 -0400

CARICOM rallies for Cuba, Jamaica Carnival is one week out, a Russian tanker slips through the blockade, the region pivots away from US trade, and Guyana's CARIFTA team is having a very good weekend in Grenada.

Cousin Leroy Seh — Jamaica, Monday April 6, 2026

Mon, 06 Apr 2026 06:30:00 -0500

Cousin Leroy, calling from the Bronx, is very proud of January's crime numbers and not worried about the fuel price.

The Yard Report — Jamaica Brief, Monday April 6, 2026

Mon, 06 Apr 2026 06:00:00 -0500

Jamaica's weekly news with the bark left on. JACDEN scandal, fuel prices up 20%, and Jamaica still cleaning up after Melissa.

Caribbean Brief – Friday, April 3, 2026

Fri, 03 Apr 2026 09:00:00 -0400

Friday Caribbean roundup — Trump's 10% tariff hits the region hard (38% for Guyana), CARICOM scrambles to respond, Jamaica gets US$50M climate fund, T&T heads into election mode, and CARIFTA opens tomorrow.

Caribbean Brief – Thursday, April 2, 2026

Thu, 02 Apr 2026 08:30:00 -0400

Thursday's Caribbean roundup — Jamaica enters World Cup playoff as favourites, T&T PM heads to Caribbean Energy Week, Haiti gang operations continue, US removes radar from Tobago, and St. Vincent gets $3M from Taiwan.

Caribbean Brief – Wednesday, April 1, 2026

Wed, 01 Apr 2026 09:00:00 -0400

Your Wednesday Caribbean roundup — Trinidad's nurse crisis, Haiti's austerity squeeze, Jamaica's budget debate, Venezuela's threats, and Carnival Corporation buying up the sea.

Caribbean Brief — Tuesday, March 31, 2026

Tue, 31 Mar 2026 00:00:00 +0000

The region watches the Middle East crisis escalate, Jamaica enters World Cup play-offs, Haiti's gangs take losses, and Rihanna's products land in Georgetown without Rihanna.

Caribbean Brief: Jamaica's Hurricane Budget, T&T Radar Gone, Guyana Plays Football & The US Removes Military Gear from Tobago

Mon, 30 Mar 2026 07:00:00 -0400

Jamaica tables its Hurricane Melissa budget, the US quietly removes military radar from Tobago, Guyana faces Belize in football, and Antigua is hosting the Commonwealth summit in November. Monday Caribbean.

Caribbean Brief: T&T Gets a US Persons-of-Interest List, Barbados Port Wins an Award & The Dominican Republic Declares Tourism War on Mexico

Sun, 29 Mar 2026 07:00:00 -0400

The US handed T&T a list of drug and gun suspects, Barbados digitised its port and won an award for it, the DR is apparently at war with Mexico over tourists, and the OAS is having an existential moment. Caribbean Sunday.

Caribbean Daily Brief — Friday, March 27, 2026

Fri, 27 Mar 2026 00:00:00 +0000

Jamaica is rebuilding after Hurricane Melissa, T&T has a new state of emergency and a FIFA match-fixing probe, Barbados swept its third straight election, and British Airways just added more seats to the islands. The region is busy.

Caribbean Brief: Jamaica Counting Hurricane Damage, T&T Gets a US List, and Sandals Is Spending Big

Tue, 24 Mar 2026 00:00:00 +0000

Tuesday's regional roundup: Jamaica's budget fight, Trinidad's US persons-of-interest list, Sandals drops $200M, and Caribbean AIDS deaths fall 60%.

Caribbean Daily Brief — Wednesday, March 19, 2026

Thu, 19 Mar 2026 00:00:00 +0000

Gas prices up in Jamaica, Trinidad extends its State of Emergency, Barbados delivers a budget and dusts off the flyover plans, and the whole region watches oil hit $100.

🌴 Caribbean Daily Brief – Tuesday, February 17, 2026

Tue, 17 Feb 2026 00:00:00 +0000

US blows up another boat in the Caribbean (133 dead now). Iran-US nuclear talks show progress in Geneva. Barbados FM challenges US due process. Mottley pushes electoral reform. Jamaica’s students stranded in Cuba. Aer Lingus launches first direct Caribbean flights.

Caribbean Daily Brief – February 14, 2026

Sat, 14 Feb 2026 00:00:00 +0000

Valentine’s Day across the Caribbean: Mia Mottley is in love with winning, the US Navy is in love with shooting boats, and Trinidad’s PM is about to sweet-talk an energy conference. Let’s go.

🇧🇧 MIA MOTTLEY SWEEPS BARBADOS — AGAIN

Barbados Prime Minister Mia Mottley has won every single seat in Parliament — for the third consecutive election. She is now only the second Caribbean leader in history to achieve a 30-0 sweep three times, joining former Grenada PM Dr. Keith Mitchell.

🌴 Caribbean Brief – Friday, February 13, 2026

Fri, 13 Feb 2026 00:00:00 +0000

Mottley’s historic third sweep. Caribbean takes centre stage in Panama. US tightening visa screws on Caribbean nationals. Italy wins at cricket. And Trinidad’s energy billions.

Caribbean Brief: Barbados Votes TODAY, Cuba on 4-Day Work Week, Jamaica Shaken

Wed, 11 Feb 2026 00:00:00 +0000

Barbados goes to the polls as Mottley seeks historic third term, Cuba adopts emergency 4-day work week over fuel crisis, Jamaica rattled by 5.0 earthquake, and Trinidad Carnival is days away.

Caribbean Brief: Barbados Votes Tomorrow, T&T PM Talks Energy, and Jamaica Mourns 'Cat' Coore

Tue, 10 Feb 2026 00:00:00 +0000

Your daily Caribbean roundup — what’s happening across the region.

🗳️ Barbados: Election Eve

Barbados goes to the polls TOMORROW (Wednesday, February 11). Schools will be closed to facilitate voting. PM Mia Mottley’s Barbados Labour Party faces what observers say is the most competitive election in years.

The Commonwealth has deployed election observers. Meanwhile, PM Mottley made headlines by slamming opposition figure Ralph Thorne’s interview with a Trinidad media outlet, suggesting external interference. Trinidad PM Kamla Persad-Bissessar has denied that her UNC party is trying to influence the Barbados result.

Caribbean Brief: Barbados Election Heats Up, Trinidad PM Addresses Energy Week, Jamaica IMF Deal, and Cuba's Humanitarian Crisis Deepens

Mon, 09 Feb 2026 00:00:00 +0000

Barbados heads to polls February 11 with schools closing for election day, Trinidad’s PM addresses Caribbean Energy Week, Jamaica’s IMF $415M deal progresses, and Cuba’s crisis worsens as US tightens the screws.

Caribbean Daily Brief: US Strikes Boats Near Venezuela, Jamaica Gets $415M Emergency IMF Loan, and T&T Says Airspace is Fine

Sun, 08 Feb 2026 00:00:00 +0000

The US is blowing up boats in the Caribbean, Jamaica needs emergency cash after Hurricane Melissa, Trinidad says everything is normal (it's not), and the T20 World Cup has kicked off.

Caribbean Daily Brief: Jamaica Gets $415M IMF Lifeline, Barbados Election Heating Up, T&T PM Blasts CARICOM, and Haiti Under Fire

Fri, 06 Feb 2026 00:00:00 +0000

Jamaica secures emergency IMF funds, Barbados gears up for February 11 election, Trinidad’s PM doubles down on CARICOM criticism, CARICOM rebukes Haiti’s leadership, and the T20 World Cup kicks off tomorrow. Your Caribbean regional roundup.

Caribbean Daily Brief — Barbados Election Next Week, Jamaica Gets IMF Emergency Cash, T&T PM Slams CARICOM, and US Visa Crackdown Continues

Thu, 05 Feb 2026 00:00:00 +0000

Barbados goes to the polls February 11th, Jamaica secures $415M IMF emergency assistance, Trinidad PM doubles down on CARICOM criticism, CARICOM rebukes Haiti leadership, US tightens visa scrutiny across the region, and Caribbean tourism takes a hit.

Caribbean Daily Brief — US Warships Still Blowing Up Boats, Barbados Heads to Polls, Jamaica Gets IMF Lifeline, and the Region Wonders What Happened to Sovereignty

Tue, 03 Feb 2026 00:00:00 +0000

The US military campaign in Caribbean waters has killed over 117 people, Barbados elections are 8 days away, Jamaica secured $415M in IMF emergency aid, Trinidad’s PM praised the boat strikes, and CARICOM can’t agree on anything except that things are complicated.

🌴 Caribbean Brief: Barbados Election Countdown, Trinidad's Police Scandal, and Carnival Season Heats Up

Mon, 02 Feb 2026 00:00:00 +0000

Barbados heads to polls February 11 with Mottley seeking a historic third term, Trinidad reels from CCTV footage of a police shooting, Carnival season kicks into high gear, and West Indies prep for T20 World Cup. Your regional Caribbean news roundup.

🌴 Caribbean Brief: Jamaica Gets $415M IMF Lifeline, US Tightens Visa Screws on Caribbean, and Trinidad Says 'We Didn't Do It'

Sun, 01 Feb 2026 00:00:00 +0000

Jamaica secures emergency IMF cash after Hurricane Melissa, the US cracks down on Caribbean birth tourism visas, and Trinidad keeps insisting it had nothing to do with the Venezuela operation. Your regional roundup.

🌴 Caribbean Daily Brief – Saturday, January 31, 2026

Sat, 31 Jan 2026 00:00:00 +0000

IMF approves US$415M emergency aid for Jamaica, Caribbean Airlines closes Barbados hub, Venezuela aftermath reshaping regional travel, West Indies cricket, and more across the islands!

Caribbean Daily Brief – Wednesday, January 29, 2026

Thu, 29 Jan 2026 00:00:00 +0000

Your regional roundup from across the Caribbean 🌴

🇯🇲 Jamaica Gets US$415 Million IMF Emergency Loan

The IMF Executive Board has approved Jamaica’s request for emergency financial assistance of approximately US$415 million to help meet urgent balance-of-payments needs. This comes as the region continues to navigate economic pressures from various global factors.

Jamaica’s Finance Minister is expected to outline how these funds will be deployed to stabilize the economy and protect vulnerable populations. The country has been a model for IMF structural adjustment programs in the past, but this emergency assistance signals ongoing challenges.

Caribbean Weekly Roundup: IMF Bailout for Jamaica, US Visa Crackdown, and Caribbean Airlines Chaos

Tue, 27 Jan 2026 00:00:00 +0000

Jamaica secures $415M IMF emergency funds, Caribbean Airlines closes Barbados hub, US cracks down on birth tourism across the region, and Venezuela conflict ripples through Caribbean tourism.

Caribbean Brief: Barbados Elections Feb 11, US Visa Crackdowns, Trinidad's AI Push, and Jamaica's IMF Return

Mon, 26 Jan 2026 00:00:00 +0000

Regional roundup: Mia Mottley goes for third term, US tightens visa rules for pregnant travelers, Trinidad partners with Microsoft on AI, and Jamaica seeks IMF help again.

Caribbean Daily Brief: Saturday, January 24, 2026

Sat, 24 Jan 2026 00:00:00 +0000

US-Caribbean visa tensions, Jamaica's IMF loan, Trinidad-US partnership, Venezuela oil law changes, and regional cricket updates

Caribbean Brief: Barbados Goes to Polls Feb 11, Trinidad's PM Kamla Warns About 'Divisiveness', Jamaica Gets $415M Hurricane Relief

Thu, 22 Jan 2026 00:00:00 +0000

Mottley calls Barbados elections for February 11, Trinidad’s new PM Kamla Persad-Bissessar navigates US-Venezuela tensions, Jamaica secures IMF emergency funding for Hurricane Melissa recovery, and Caribbean Airlines restructures its regional operations.

Caribbean Daily Brief — January 21, 2026

Wed, 21 Jan 2026 00:00:00 +0000

Jamaica secures US$6.7 billion for Hurricane Melissa recovery, Maduro claims presidency from Brooklyn jail, Haiti TPS termination hearing continues, and Trinidad welcomes new PM Stuart Young.

Caribbean Daily Brief – January 20, 2026

Tue, 20 Jan 2026 00:00:00 +0000

Your 5-minute tour of regional chaos, served with rum punch

🇻🇪 THE MADURO SITUATION: STILL SITUATING

Two weeks after Uncle Sam yoinked Nicolás Maduro out of Caracas like a bad tooth, the Caribbean is still dealing with the hangover. Thousands of tourists got stranded. Cruise ships played musical chairs in Barbados harbour. And Trinidad? Well, T&T said “sure ting” to letting U.S. military use their airports, which Venezuela called a betrayal. PM Kamla then spent the weekend cussing out the Energy Chamber for allegedly caring more about foreign oil companies than local contractors. Classic Trini Monday.