HAVANA — The nominee for U.S. Secretary of State, Sen. John Kerry, once held up millions of dollars in funding for secretive U.S. democracy-building programs in Cuba. Defense Secretary hopeful Chuck Hagel has called the U.S. embargo against the communist-run island “nonsensical” and anachronistic.

Both men are now poised to occupy two of the most important positions in President Barack Obama’s Cabinet, leading observers on both sides of the Florida Straits to say the time could be ripe for a reboot in relations between the longtime Cold War enemies — despite major obstacles still in the way.

Kerry’s confirmation hearing was held last Thursday, with Hagel’s likely to begin next Thursday. In a day marked by platitudes and praise from his longtime colleagues, the Massachusetts Democrat up for top U.S. diplomat sidestepped two questions on Cuba without giving any hint of his opinion on bilateral relations.

Yet Kerry’s record has showed some openness to relaxing the tough U.S. stance on Cuba.

“I think having a secretary of state and secretary of defense who understand and are willing to speak publicly that isolation is counterproductive is a very good start,” said Tomas Bilbao, executive director of the nonpartisan Cuba Study Group, which advocates using engagement to spur democratic change. “I’m optimistic about the opportunity.”

Carlos Alzugaray, an ex-Cuban ambassador to the European Union and the author of several studies about Cuba-U.S. relations, said that if both men are confirmed, no Cabinet since the Carter administration would have such high-level voices in favor of rapprochement.

At the same time, the composition of Cuban-Americans in Florida is evolving, with younger voters less emotionally attached to the issue than their parents and grandparents. Exit polls showed 49 percent of Cuban-Americans in the state voted for Obama, roughly the same percentage as four years ago, an indication the group no longer plays the make-or-break role it once did in presidential politics.

The atmosphere is changing in Cuba as well.

Alzugaray noted that the island has taken many steps that would normally be welcomed by Washington such as freeing dozens of political prisoners, opening the economy to limited capitalism, hosting peace talks for war-torn Colombia and eliminating most restrictions on travel for its own citizens.

The greatest obstacle to better ties is undoubtedly the continued imprisonment of U.S. contractor Alan Gross, who is serving a 15-year sentence for crimes against the state after he was caught setting up clandestine Internet networks as part of a U.S. Agency for International Development democracy-building program.