迈阿密的古巴商界菁英一再为后共产主义的转型做准备：在苏联解体后委托制定重建计划，约 10 years ago 的美古关系解冻期间又做过一次；但他们如今主张，可能在 1990s 甚至 2015 还存在的可投资「商业案例」已经被侵蚀。Carlos Saladrigas 这位 77-year-old 的迈阿密企业主管，1961 透过 Operation Pedro Pan（将数千名无人陪伴的儿童带到美国）离开古巴，他说古巴当前在经济与基础设施上的需求如此庞大、政治又如此根深蒂固，以致一场由美国主导的转型所仰赖的私人资本，比过去那些乐观循环更难动员。

随著 Donald Trump 声称哈瓦那濒临崩溃、而美国官员释出他们希望看到政府垮台的讯号，美国的施压已加剧；同时，总统 Miguel Diaz-Canel 表示古巴「ready」谈判，但前提是没有先决条件，且必须「from a position of equals」。在地面上，长期停电与短缺使经济陷入瘫痪，并在过去 decade 迫使几乎 1 in 5 的居民出逃；在美国于 January 3, 2026 透过在委内瑞拉移除盟友 Nicolas Maduro 而有效切断古巴的石油生命线之后，燃料日益吃紧引发紧急措施：航空公司被警告可能无法在哈瓦那加油，从供水与污水到道路、港口、学校、医院等基本系统都在恶化。仅电力网在 roughly 1 year 内就发生约 6 次全国性故障，且有人估计至少需要 $10 billion 才能稳定，这凸显为何华盛顿的委内瑞拉剧本被视为不适用于自 1959 革命后不久起、在一党共产统治下已约 6 decades 的古巴。

一个核心限制是：缺乏明显的内部接班人或可被利用的派系，无法类比委内瑞拉 post-Maduro 的领导层；再加上古巴共产党坚称一党统治不可谈判，让投资人必须在投入之前，要求对民主制度、资本保护与人权提供更深层的保障。诱因也不同：委内瑞拉庞大的石油储量让美国领导人得以把介入包装成在经济上可自我支撑；而古巴缺乏可比拟、可「easy-to-seize」的资产，于是问题变成华盛顿是否愿意花 $2 billion to $3 billion 去衔接一段 2 to 3 year 的过渡期。尽管如此，地理邻近与潜在能力仍让兴趣未灭：古巴距离 Florida 约 90 miles，从迈阿密飞行 roughly a 45 minute，已投资兴建新的但多半空置的饭店房间（使「tourism」成为最接近石油的类比），并在医学、科学与制药方面保有人力资本，同时拥有大片未充分利用、可供应美国农产品的农地；支持者指出，即使是 Obama-era 的 2016 那一刻开放，也曾引发民间规划，最快可在 90 day 内完成「turnkey」的农业设置；然而自 1960s 以来数十年一次次落空的预测，让倡议者警告当前危机或许前所未有，但仍在政治上难以转化为持久、可融资的转型。

Miami’s Cuban business elites have repeatedly prepared for a post-communist transition, commissioning rebuild plans after the Soviet Union’s collapse and again during the US-Cuba thaw about 10 years ago, but they now argue the investable “business case” that might have existed in the 1990s or even 2015 has eroded. Carlos Saladrigas, a 77-year-old Miami executive who left Cuba in 1961 via Operation Pedro Pan (which brought thousands of unaccompanied children to the US), says Cuba’s current economic and infrastructure needs are so large, and its politics so entrenched, that the private capital a US-led transition would depend on is harder to mobilize than in prior cycles of optimism.

US pressure has intensified as Donald Trump claims Havana is near collapse and US officials signal they would like to see the government fall, while President Miguel Diaz-Canel says Cuba is “ready” for talks only without preconditions and “from a position of equals.” On the ground, prolonged blackouts and shortages have paralyzed the economy and driven nearly 1 in 5 residents to flee over the past decade; after the US effectively cut off Cuba’s oil lifeline on January 3, 2026 by removing ally Nicolas Maduro in Venezuela, emergency measures have followed as fuel tightens, airlines are warned they may not be able to refuel in Havana, and basic systems from water and sewage to roads, ports, schools, and hospitals are deteriorating. The power grid alone suffered about 6 nationwide failures in roughly 1 year and is estimated by some to need at least $10 billion to stabilize, underscoring why Washington’s Venezuela playbook is seen as a poor fit for a Cuba that has spent about 6 decades under one-party communist rule since shortly after the 1959 revolution.

A central constraint is the absence of obvious internal successors or exploitable factions akin to Venezuela’s post-Maduro leadership, plus the Cuban Communist Party’s insistence that one-party rule is non-negotiable, making investors demand deeper guarantees on democratic institutions, capital protections, and human rights before committing. The incentives also differ: Venezuela’s vast oil reserves let US leaders frame intervention as economically self-funding, while Cuba lacks comparable “easy-to-seize” assets, raising the question of whether Washington would spend $2 billion to $3 billion to bridge a 2 to 3 year transition. Still, proximity and latent capacity keep interest alive: Cuba sits about 90 miles from Florida, is roughly a 45 minute flight from Miami, has invested in new but largely empty hotel rooms (making “tourism” its closest analogue to oil), and retains human capital in medicine, science, and pharmaceuticals alongside large stretches of underused farmland that could supply US produce; proponents note even an Obama-era 2016 moment of openness sparked private plans as fast as a 90 day “turnkey” agricultural setup, yet decades of failed forecasts since the 1960s leave advocates warning that the current crisis may be unprecedented but still politically difficult to convert into a durable, financeable transition.