That was when the House of Representatives, obviously put off by the administration's bizarre obsession with Cuba, sharply contradicted the President by voting to overturn his prohibition on sending certain types of packages to the island.
The vote was 221 to 194 against funding the new restrictions, which would punish people in the U.S. for sending - listen to this - clothes and personal hygiene products to their families in Cuba. Bush should take note of the fact that 46 Republicans voted with the Democrats.
"These are regulations that restrict the freedom of American citizens," said Rep. Jeff Flake (R-Ariz.), who sponsored the amendment despite a telephone call from the White House asking him not to do it. "Let's allow Cuban-Americans to observe the freedom they have to send food, medicine and hygiene items to their people in Cuba."
Mayra Rodríguez, a Cuban-American businesswoman who left her native country 25 years ago, agreed.
"These measures are not against Fidel Castro," she said angrily. "They are against the Cuban family and against us, the people who left Cuba and came to the U.S. seeking democracy and freedom. They violate our rights. I would have voted for Mr. Bush, but not anymore."
She is not the only one.
A recently conducted survey of 812 Cuban-Americans by the William C. Velasquez Institute (WCVI) and the MirRam Group showed that the new regulations limiting travel and remittances to Cuba are undermining the President's support among his most loyal voters in Florida.
While Florida Cubans voted 82% for Bush in 2000, only 66% said they would support him today. According to the findings, a solid one-third of Cubans are disenchanted with his Cuba policy.
"President Bush's new restrictions have divided our community," said Álvaro Fernández, president of the recently created Cuban American Commission for Family Rights, a co-sponsor of the survey. "While intended to gather support, the President's measures are causing his most loyal base to consider other electoral options."
Enforcement of the restrictions began last month. They limit family visits to once every three years instead of once a year. In addition, the spending limit for Cuban-Americans (it does not apply to any other visitor to the island) was reduced to $50 a day, down from $167.
Also, the new sanctions limit remittances of money to "immediate" family members - no aunts, uncles or cousins - and even restrict shipments of food, clothing and medical supplies.
To top it all, humanitarian travel - that is, a special trip to see a gravely ill relative or attend the funeral of a loved one - also is prohibited. All in the name of freedom and human rights.
The sanctions are not only cruel and bizarre - Cuba is the only country Americans are forbidden to visit - but after 43 years of a failed trade embargo, no one in their right mind can really believe that they will advance democracy in the island.
Yet they could make Bush lose the all-important state of Florida. Four years ago, he won it by the slimmest of margins - a little more than 500 votes. He cannot afford to lose thousands of Cuban-American voters. But that is exactly what's happening: Thousands of Cuban-Americans who would have voted for Bush feel betrayed, discriminated against and persecuted.
"Something has to change," Rodríguez said. "Everybody has the right to travel freely except Cuban-Americans? But rights are supposed to apply equally to everyone - and Cuban-Americans cannot be the exception."
The administration is playing a cynical political game with the lives of Cubans and Cuban-Americans. And come November, it may find out it was not a very smart thing to do.