There hasn’t been a sitting U.S. president on Cuban soil since 1928, but Barack Obama kept his promise to go to Cuba in the latest step toward normalizing relations with the island’s Communist regime. While Obama seeks primarily to build his legacy, the ramifications of this visit will contribute to it in a way he doesn’t intend.

The trip didn’t get off to a good start, either. When Obama disembarked Air Force One at Jose Marti International Airport, Cuban President Raul Castro was not there to greet him, even though the communist thug routinely greets foreign dignitaries at the airport.

The imagery likewise is terrible. Investor’s Business Daily ponders, “As a sycophantic media rolls out the adoring photos and flattering words, it’s hard to say what will prove most embarrassing: the picture of President Obama posing in front of a communist cement wall emblazoned with a pop-art depiction of the murderous — and racist — ‘revolutionary’ Che Guevara, a man who sought to set off a nuclear bomb against the U.S. in the early 1960s? Or the photo of 84-year-old Cuban communist dictator Raul Castro diabolically leering as he lifts the limp wrist of President Obama while he giggles like an unwitting teenager?”

Obama’s trip to Cuba is part of realizing his foreign policy vision, and he hopes that his visit to the brutal regime will “encourage generational evolution.” Surely, the Cuban people are hoping for the same, but as long as they live under the brutal rule of the Castro regime there will be little that the minister of hope can change. And nothing Obama has done actually weakened that regime; on the contrary, he has legitimized it.

One of the topics for conversation with Castro was freedom of speech and assembly. So it speaks volumes that just hours before Obama arrived, the Cuban police broke up a larger than normal crowd of political dissidents known as the Ladies in White and hauled many of them off to detention facilities. That would be the same Ladies in White Obama promised in a March 10 letter to meet.

Castro effectively denied even holding political prisoners: “Give me a list and I’ll release them,” he said, adding, “If we have those political prisoners they will be released before tonight ends.”

They weren’t released, and Obama remained silent.

Worse, on Monday Obama lamely accepted Castro’s criticism of the U.S. on human rights: “I actually welcome President Castro commenting on some of the areas where he feels where we’re falling short because I think we should not be immune or afraid of criticism or discussion as well.” Does Obama mean to imply that he’s falling short on jailing dissidents here in America?

As for free speech for members of the Cuban opposition, The Wall Street Journal’s Mary Anastasia O'Grady predicted, “The regime will turn out plenty of compliant Cubans who will tell reporters that the embargo is the source of Cuban poverty.” It’s all political theater.

O'Grady further noted, “Yet even if there is a U.S nod to the opposition, there also will be a wink, as the president poses with the dictator along with members of the Colombian terrorist group FARC — invited by Mr. Obama — at a baseball game and pushes for U.S. policies that will finance the totalitarian apparatus. The big lie will be that by legalizing commercial and banking relations with Cuba, the U.S. will empower the Cuban people. The opposite is true.”

In other words, given the backdrop of people with whom Obama will pose, who does he really side with — the Cuban people or the Cuban dictators? The question answers itself.

As for the embargo, the idea of opening up business with Cuba along with lifting the embargo on trade is a complete reversal of U.S. policy for the last 50 years. This isn’t to say the policy has been entirely effective — the Castros are, after all, still in power. Some say Obama’s move in a different direction could open the Caribbean island to Liberty via free trade, especially as the young generation learns the value of capitalism.

Then again, Europe, Latin America, Canada and Asia have been trading with Cuba for decades to no avail.

Obama claims his visit will reduce tensions between the U.S. and Cuba and bring about change in the region. Given that the Castros are ideological kindred spirits with Obama, however, it’s doubtful that the Cuban people will benefit from Obama’s display. Recall that Obama’s mentor was avowed Communist Frank Marshall Davis, and it’s very possible that Obama’s desire to renew relations with Cuba will make things worse instead of better for those under Castro’s iron fist.

How so? Consider that if American money starts flowing into the Cuban economy, the Castro regime will undoubtedly use the funds to further solidify its power over the Cuban people. Funding dictators and coddling up to them, whether directly or indirectly, rarely works out well for the advancement of freedom.

Does anyone really think that Obama is visiting Cuba to help that nation set a path toward freedom? Given his administration’s relentless assault on Liberty in our own country, it may be delusional to think so.