It is Bush's vision for Cuban regime change: providing help on the outside, prodding change on the inside.
Seizing on Castro's fading health as a rare opening, Bush was to ask other nations Wednesday to help Cuba become a free society.
In remarks prepared for delivery at the State Department - his first standalone address on Cuba in four years - Bush looks to the day when Castro is gone. Bush describes a nation in which Cuban people choose a representative government and enjoy basic freedoms, with support from a broad international coalition.
For now, though, Castro is still the island's unchallenged leader, as he has been for almost 50 years. And he remains a nemesis to Bush, whom he accuses of being obsessed with Cuba and of threatening humanity with nuclear war. At the age of 81, Castro is ailing and rarely seen in public. But life has changed little on the island under the authority of his brother, 76-year-old Raul Castro, who has been his elder brother's hand-picked successor for decades.
Bush was expected to tout peaceful, pro-democracy movements in Cuba and call on other countries to get behind them. In a direct appeal to ordinary citizens in Cuba, he was to tell them they have the power to change their country, but the White House says that is not meant to be a call for armed rebellion.
Bush proposes at least three initiatives: the creation of an international "freedom fund" to help Cuba's potential rebuilding of its country one day; a U.S. licensing of private groups to provide Internet access to Cuban students, and an invitation to Cuban youth to join a scholarship program.
The latter two offerings help the Bush administration underscore the kind of real-life limitations that Cubans now face, from blocked Internet access to restricted information about their leaders to denial of legal protections. The creation of the international fund is meant to speed up societal transformation.
"We all know that Cuba is going to face very significant requirements to rebuild itself," said a senior administration official, who spoke on condition of anonymity to avoid pre-empting the president. "There's a whole set of challenges that Cuba is going to face. The United States will clearly want to help the Cubans as they define what it is they need, but we think the international community should be thinking that way as well."
Washington's decades-old economic embargo on Cuba prohibits U.S. tourists from visiting the island and chokes off nearly all trade between both countries. Bush will ask Congress to maintain the embargo, which has come under scrutiny and calls for reassessment from some lawmakers.
Cuba staged municipal elections on Sunday, the first step in a process that will determine whether Fidel Castro is re-elected or replaced next year. The Communist Party is the only one allowed, and while candidates do not have to be members, critics claim they are the only ones who ever win.
Bush, increasingly, is speaking of a Castro-free Cuba. As he put it earlier this month: "In Havana, the long rule of a cruel dictator is nearing an end."