Despite Canada's historically un-U.S.-like relationship with Cuba, it was still somewhat surprising to hear the right-leaning Baird endorse enthusiastically Obama's overture to Raul Castro. "I agree with this policy. I don't think previous U.S. policy has been effective," he said. "If you flood Cuba with American values, American people, and American investment, it will help transform the country."

Critics of this theory point to China and Vietnam, two countries with deep economic ties to the U.S. in which one-party communist rule still obtains. I asked Baird about this argument, and he responded by nodding in the direction of a popular counterargument—that Cuba has been held to a separate and hypocritical double standard by successive U.S. presidents.

"It's hard to compare two situations together, but if you can have normalized relations with Vietnam, why wouldn't you normalize relations with Cuba?" Baird asked.

Normalization with Vietnam has not made it any freer, I argued. "Certainly it's improved the economic lot of the Vietnamese people. The average family is better off today than it was 20 years ago." He then noted—in very diplomatic terms—that even bigger changes are coming in Cuban politics. "Obviously there will be further change when people move on," he said, a reference to the age of the Castro brothers.

I raised one other issue with Baird on this subject: whether he thought the Iranian regime might interpret Obama's opening to Cuba (an opening the Cuban government is naturally framing as a victory for the revolution) as a sign of American weakness in the ongoing nuclear negotiations. "Did anyone say that the U.S. was a pushover when you normalized relations with Vietnam?" Baird asked. "I don't accept that."

Do you think, I asked, that the Iranians have a full understanding of American will on this subject?

"No," was Baird's one-word answer.

Do you have a full understanding of American will on the subject? I asked.

"I take the president at his word," he said. "They say they'd rather have no deal than a bad deal." Then Baird smiled. "We might have a different understanding, however, of what constitutes a bad deal."