Image: A classic American car in Camagueey, Cuba © Getty Images

Is this the year we finally say hasta la vista to the five-decade-old Cuban trade embargo?

Tom Herzfeld, a Miami-area fund manager who studies Cuba-U.S. relations, thinks so. This is an unconventional view. But stranger things have happened in the past few years, like the Arab Spring. Besides, it's often the unexpected that provides the best returns in investing.

And here, the investment implications could be big, for several companies.

Herzfeld thinks the policy change would boost companies as diverse as cruise line operator Carnival (CCL), cargo shipper Seaboard  (SEB), regional airline Copa (CPA), soft-drink distributor Coca-Cola Femsa (KOF) and even Watsco (WSO), which likely would sell more air conditioners in Cuba.

These stocks are all big holdings in the Herzfeld Caribbean Basin (CUBA) fund, which Herzfeld says he has positioned to benefit from embargo elimination.

"Now, more than ever, the pieces are falling into place where the embargo could be lifted this year," maintains Herzfeld.

Why now?

Herzfeld cites President Barack Obama's view that economic relations with Cuba should be liberalized -- and the president's greater freedom to pursue this goal now that the election is behind him.

Herzfeld points to the nomination of Sen. of John Kerry,D-mass., who shares this view, to lead the State Department, as well as to steps by Cuba to improve human rights, such as the recent loosening of travel restrictions for Cubans.

Then there's the shaky health of Cuban dictator Fidel Castro, whose demise could lead to big changes.

Michael Brush

Michael Brush

"I believe if he were to die, that would be the single event that would led to the lifting of the embargo," says Herzfeld. 

A possible leadership transition in Venezuela, which we'll get to in a moment, could also be a factor  in the embargo coming down.

Cuban experts I surveyed don't think much of Herzfeld's theory. "It won't happen anytime soon," predicts Ted Piccone, a senior fellow and deputy director for foreign policy at the Brookings Institution.

Riordan Roett, the director of the Latin American Studies Program at the Johns Hopkins School of Advanced International Studies, puts it more bluntly: "What's he smoking?"

Cuba experts cite two main obstacles. First, the embargo is in place because of a law passed by Congress, which Obama can't just overturn on his own. Next, Cuban-American congressional leaders, who have a big say, strongly oppose any change. Top among them: Sen. Robert Menendez, D-N.J., who may be taking over the Senate Foreign Relations Committee; Rep. Ileana Ros-Lehtinen, R-Fla., former chairwoman of the House Foreign Affairs Committee; and Sen. Marco Rubio, R-Fla.

"They are just not going to budge on this," says Roett.

As an investor, Herzfeld is nonplussed by these challenges. He thinks the companies his fund owns as Cuba plays will do well regardless of whether the embargo is ended. Many of the stocks have recently hit all-time highs. An end to the embargo would be just one more catalyst for these names, he says.

There are two other reasons investors may want to avoid getting too put off by the Cuba experts. First, in investing, it's the out-of-consensus plays that can do the best -- when things occur that most people did not foresee.

Plus, I can make the case that it's not too crazy to think that the embargo is on the way out. It would not be the first time  "the experts" missed a big change. How many of them predicted the Arab Spring?

Even if an Arab Spring doesn't sweep Cuba, there are plausible reasons to think the trade embargo could be gone sooner than the experts believe. Here are the three big ones:

1. The embargo doesn't make any sense anymore.

Sure, Fidel, 86, and his brother Raúl Castro, 81, are bad hombres. They've confiscated a lot of property -- much of it owned by U.S. companies -- since seizing power in 1959. Worse, they stomp on human rights and oppose democracy. This is why the 1996 Helms-Burton Act blocks most U.S. trade with Cuba until the country has free elections, releases political prisoners and respects human rights.

It is a commendable policy but, sadly, hypocritical. If this were consistent U.S. policy, we'd have no political or trade relations with Vietnam, Myanmar or even China, says Juan Carlos Hidalgo, a Latin America policy analyst at the Cato Institute, who notes that each of these countries fails to clear the Helms-Burton hurdles applied to Cuba.

Thus, the Cuba embargo is a pretty glaring anomaly, which makes it vulnerable. "The only advantage of the embargo is that it allows the Cuban regime to blame the miserable Cuban economy on 'the blockade' as they call it," says Hidalgo.

The embargo is also vulnerable because it's an obvious failure. After 50 years of embargo, the Castro brothers still rule Cuba, notes Tomas Bilbao, the executive director of the Cuba Study Group, a lobbying organization whose goal is "empowering" Cuban people by helping them start businesses and sell goods abroad. "I think we need to shift from an obsession with hurting the regime to an obsession with helping the Cuban people," he says.

2. Political support for the embargo is eroding.

Another problem for embargo aficionados is that younger Cuban Americans in Florida, the all-important next generation of voters, just aren't as passionate about it as their parents and grandparents were. "When I lecture down there, they couldn't care less about Castro and the embargo," says Roett.

Click here to become a fan of MSN Money on Facebook

A recent poll by Florida International University in Miami bears this out. It found that just 50% of Cuban-Americans still support the embargo, and 80% think it has failed. It's also worth noting that Obama got a lot more of the Cuban-American vote in Florida in the 2012 election, despite the awareness that he is more willing to lift the embargo, says Hidalgo.

With their constituents defecting on the issue, congressional backers of the embargo may be losing ground. "The Cuban vote in Florida is changing, thus sticking with the embargo doesn't makes sense," believes Hidalgo.

3. Venezuelan President Hugo Chávez may be on his deathbed

The big wild card in all this is Venezuelan President Hugo Chávez, who may be rapidly losing his fight against cancer. Here's why his demise could lead to an end to the embargo.

Chávez has an unusually close personal and ideological relationship with Fidel Castro that goes back many years. This explains why Venezuela subsidizes the Cuban economy to the tune of about $8 billion worth of oil a year. It's not clear that whoever succeeds Chávez would continue the oil subsidy. Without it, says Roett, the Cuban economy would tank and a social crisis would ensue.

That might either force out the Castro brothers or pressure them to pass the torch and make the political and economic reforms needed for the U.S. to lift its embargo and possibly lend the economic aid that would avert chaos.

"Change will only come when the octogenarians who are running Cuba today have no choice but to open up in a meaningful way," says Roger Noriega, a former assistant secretary of state for Western Hemisphere affairs who now directs Latin American studies at the American Enterprise Institute. "They've only adopted reform when they were under pressure." An end to the Venezuelan oil subsidy and ensuing economic problems might create that kind of pressure.

Helms-Burton calls for the U.S. to support any transitional reform government. Thus, Cuban domestic reform might attract U.S. aid  that could be needed to avoid economic and social chaos if Venezuela pulls away after Chávez.

If the embargo goes away and Cuba transitions toward a market economy, these companies could benefit, maintains Herzfeld.

Consumer plays

Cruise line companies Carnival and Royal Caribbean Cruises (RCL) would benefit from an end to the embargo, since they'd have a whole new market. Cruises to Cuba would be a popular way for turistas to see the country, out of necessity, since hotels are in a poor state in Cuba. "If the embargo were lifted, their Caribbean business would double," says Herzfeld.

Michael Scanlon, an analyst with the John Hancock Balanced (SVBAX) fund, likes Carnival in part because it looks cheap. A key valuation  metric here is enterprise value (market cap plus net debt) per "available berth per day," or the number of available beds per day. It is currently at $535, compared with almost $1,000 in 2006. Scanlon believes ticket pricing should improve because cruise companies are limiting capacity expansion over the next few years. And a lot more boomers, a key cruise demographic, are moving into retirement.

Copa, a Panama-based regional airline serving Cuba, would benefit from an upturn in travel from the United States. The carrier already stands to gain from Cuba's recent loosening of travel restrictions on its citizens, says Herzfeld. "This is a very major change in policy," he says. This reform will help Copa even if the embargo is not lifted, because Cubans will be traveling more throughout the region.

Coca-Cola Femsa would see a lift in business in Cuba, as the distributor of Coca-Cola in Central and Latin America, though you can already buy Coca-Cola in Cuba.

Transport plays

Seaboard is the largest container carrier in the Caribbean, so it would benefit from greater U.S. trade with Cuba and a revitalization of Cuba's economy, says Herzfeld. He also expects gains for the Norfolk Southern (NSC), railroad. "We believe a lot of freight for Cuba that comes down the East Coast to Florida will be shipped on their railroads."

Infrastructure plays

"If the embargo with Cuba is lifted, there will be boom in Cuban infrastructure development," says Herzfeld. This could help MasTec (MTZ), a Florida infrastructure construction and engineering company. It would also help Vulcan Materials (VMC) and Martin Marietta Materials (MLM), which sell granite, limestone, sand, gravel and cement used in construction, and Watsco, which sells air conditioners. Florida-based homebuilder Lennar (LEN), would also pick up business in Cuba, he predicts.

Herzfeld Caribbean Basin Fund

You could also buy shares of the Herzfeld Caribbean Basin Fund, which Herzfeld has positioned to benefit from an end to the embargo. This is a closed-end fund, a kind of investment company that raises investment capital and then issues a fixed number of shares. The shares then trade throughout the day like stocks, moving up or down as the value of the fund's holdings change.

Herzfeld's fund looks cheap, because it currently trades at about a 7% discount to its net asset value, or the value of the stocks it owns. The NAV is currently around $9 per share, says Herzfeld. But the fund shares sell for around $8.38. The fund has historically been sensitive to Cuba-related news, and at some point almost every year, it rises above its net asset value.

"The holdings will continue to do well, even if nothing changes in U.S.-Cuban relations," predicts Herzfeld. "If the embargo is lifted, they will get a significant amount of new business." Herzfeld and his family are the fund's biggest shareholders. This fund's stock is up by an annualized 16% a year over the past 10 years.

Of course, betting on an end of the embargo assumes that Cubans still have enough entrepreneurial spirit -- after 50-plus years of living in a government-run economy -- to create and run businesses vigorously enough to make an economy hum. 

Click here to become a fan of MSN Money on Facebook

"It is going to be extremely hard for Cubans to leave that mentality of depending on the government and take chances," says Hidalgo. But he thinks it would happen. After all, he says, Cuba was one of the most developed Latin American countries when Castro took over, and the culture behind that achievement is not totally gone. "You still see a lot of underground economic activity, which means that the capitalist spirit is there," says Hidalgo. "The communist regime has not erased that capitalist spirit."

At the time of publication, Michael Brush did not own or control shares of any company or fund mentioned in this column.

Michael Brush is the editor of Brush Up on Stocks, an investment newsletter. Click here to find Brush's most recent articles and blog posts.