Chronology of U.S.-Cuba relations in the second term of Trump Presidency

The United States and Cuba have been on the rise as the Cuban authorities indicated on Feb. 25 that their border guards fired and killed four and injured six individuals in a speed boat owned in Florida which it claimed was trying to carry out a terroristic infiltration into the island.

The interior ministry at Cuba claimed that the ship fired after it was intercepted in Cuban waters. U.S. Secretary of State Marco Rubio termed the episode as very unusual and that Washington was investigating the case, indicating that no U.S. government officials were involved. This tussle is fought against the background of increasing tensions after U.S. actions that interrupted the flow of oil to Venezuela, one of the Cuban allies, aggravating the fuel crisis in the island.

Here’s a chronology of events ever since US President Donal Trump took over in his second term on Jan 20, 2025:

CHRONOLOGY: U.S.-Cuba relations in the second term of Trump

The following represents a chronoogy of events in the United States and Cuba relations since the start of the second term of President Donald Trump on Jan. 20, 2025.

Jan. 20, 2025 – Trump assumes office in addition to the former president, Joe Biden, issues executive orders implementing the removal of some of its sanctions and more economic ties to Cuba.

Jan. 20, 2025 – The Administration reinstates rigid workforce of sanctions, which hinder U.S. monetary dealings and business connections with narrow entities of the Cuban government.

Jan. 21, 2025 – Trump administration initiates rescinding of humanitarian initiatives of parole programs permitting Cubans to have more legal migration avenues.

Feb. 3, 2025 – U.S. authorities renew the Cuba designation as the State Sponsor of Terrorism and enforce iPu and IoO banking access as well as in international transactions.

Feb. 18, 2025 – Secretary of state Marco Rubio announces that Washington will continue imposing sanctions on Cuba unless it makes political and economic reforms.

March 12, 2025 – U.S. Treasury intensifies enforcement inspection of Cuba-linked financial transactions on the by foreign companies and banks.

May 27, 2025 – Administration restates its policy of economic pressure and threatens attempts to evade the U.S. sanctions.

Aug. 14, 2025 – American officials announce that the total embargo and investment and trade restrictions will still be in place against Cuba government-supported organizations.

Jan. 9, 2026 – The Trump administration indicates that it will keep enforcing the sanctions as Cuba is facing an aggravated economic and fuel crisis.

Feb. 25, 2026 – U.S. permits some fuel related transactions on humanitarian grounds in favor of the Cuban private sector without withdrawing their original core sanctions.

US Dockworker Strike Paralyzes 36 Ports; Impact and Possible Future Scenarios

The United States is currently in the throes of the largest dockworker strike in nearly half a century. The International Longshoremen’s Association (ILA), representing 45,000 port workers from Maine to Texas, has initiated a significant stoppage. The first of its magnitude since 1977, the strike has resulted in long lines of container ships queuing up outside major U.S. ports, threatening shortages of everything from bananas to auto parts.

The strike was triggered by a breakdown in negotiations for a new six-year contract between the ILA and the United States Maritime Alliance (USMX), the employer group representing the port owners and shipping companies. The ILA is seeking a significant pay raise and commitments to halt port automation projects, which the union believes will lead to job losses. The USMX had offered a 50% pay increase, but the ILA considers this insufficient.

As the strike entered its third day, at least 45 container vessels that had been unable to unload had anchored up outside the strike-stricken East Coast and Gulf Coast ports. This was a significant increase from just three before the strike began. Many vessels seem to have decided to wait it out, possibly hoping for a prompt resolution to the strike action.

The International Longshoremen’s Association (ILA) has halted the U.S. supply chain with the largest dockworker strike in nearly half a century. As port workers from Maine to Texas walk off the job, the reverberations are already being felt, and the stakes are growing.

Immediate Impact: A Deepening Logjam

In just three days, the number of container ships anchored outside East Coast and Gulf Coast ports has skyrocketed, with 45 vessels now stranded, a sharp rise from the pre-strike three. This figure is expected to double before the week’s end, creating a cascading backlog that could take months to untangle.

Goods ranging from fresh produce to essential auto parts are stalled, with no immediate resolution in sight. While West Coast ports remain an option, rerouting through the Panama Canal is costly and time-consuming, further exacerbating global shipping delays.

Retailers have been bracing for impact. The U.S. economy could see a chilling effect as the $5 billion daily cost of the strike piles up. Although economists suggest companies front-loaded key imports in anticipation of labor unrest, a prolonged disruption would ignite supply shortages, especially for food and perishable goods.

The National Retail Federation, already warning of “devastating consequences,” is pushing for immediate federal intervention.

Political Calculations: Biden Walks a Tightrope

With the strike happening under the watch of a pro-labor president, the Biden administration finds itself in a precarious spot. While the president has aligned with the union, urging employers to sweeten their offer, political ramifications loom large.

The administration’s reluctance to use federal authority to break the strike, citing long-term economic recovery goals and labor support, could alienate business leaders and voters grappling with inflation.

Yet, invoking the Taft-Hartley Act, which would force workers back to the docks, carries risks. Such a move, particularly ahead of the November election, could harm Democratic support among labor groups. The balance between addressing immediate economic concerns and long-term political calculations remains razor-thin.

The Ripple Effect: Supply Chain and Consumer Prices

If the strike drags on, the economy could face another inflationary wave, particularly in food prices. While some sectors remain insulated by preemptive shipping, others will not be so fortunate. A prolonged stoppage would hike shipping costs, which could be passed down to consumers already weary of high living expenses.

Economists are cautious about drawing parallels to previous disruptions, as the strike now hits during a period of heightened inflationary pressures. Consumer sentiment, already fragile, could suffer if essentials become more scarce and expensive, setting the stage for a political and economic standoff.

What’s Next: Automation or Appeassement?

The strike raises key questions about the future of labor relations in the U.S. economy. Automation has emerged as a flashpoint in negotiations, and with the ILA calling for a halt to port automation projects, the outcome could define the scope of labor’s influence on technological advancements.

For now, the supply chain stands at a crossroads. If no deal is reached, the possibility of intervention, economic fallout, and a lasting labor standoff could leave scars that extend well beyond the ports.

Whether the ILA and USMX find a middle ground or continue to dig in will determine the scale and scope of the economic damage. One thing is certain: the stakes are high, and the clock is ticking.