If one moment can perfectly capture the amalgam of arrogance and absurdity that is President Obama, his handshake with Cuba’s Raul Castro would be it:

In the moments after the end of a historic press conference held by President Barack Obama and President Raul Castro in Havana, Cuba, what began as a regular handshake morphed into … something else. The Cuban leader raised Obama’s limp arm above his head and held it there for a few seconds.

The move most closely resembled a wrestling referee announcing the winner of a wrestling match. Only way more awkward.

To say that picture went viral on social media would be an understatement:

As Stella so aptly notes, some supporters are less than comfortable with Obama’s “Spring Break” in Cuba. Fox News contributor and staunch progressive Juan Williams says the trip is a mistake, especially based on his family’s experience in fleeing oppression in Panama:

…America’s left-wing academics and Hollywood celebrities have long romanticized Latin American strongmen as righteous revolutionaries, opposed to mid-20th century American military and business dominance of the region.

But to people living in those nations, the reality is that the revolutionaries became cruel, oppressive dictators in the case of Arias, the late Venezuela President Hugo Chavez and most of all, Fidel Castro.

Given my scars, President Obama’s trip to Cuba later this month leaves a bitter taste in my mouth.

To me, it is painful to see the president of a nation based on individual liberty and protection of rights under law have to keep silent about the thousands of people who have suffered oppression at the hands of the Castro regime.

The ensuing meetings are likely going to be even more awkward.

In an extraordinary news conference Monday afternoon, President Obama and Cuban President Raúl Castro sparred over human rights, the Guantanamo prison and their views of their own countries and the world, even as both hailed Obama’s historic visit here as a new step in normalizing relations.

The event was marked by a jarring juxtaposition of diplomatic formality and public jousting, as Castro responded to questions from American reporters by either ignoring them or dismissing them as misguided. At one point, he challenged a U.S. journalist to “give me a name” of any alleged political prisoner here.

Naming oppressed political opponents might have been easier for members of the press if the Castro brothers didn’t have them rounded up prior to Obama’s visit.

Women demanding free speech and democracy in Cuba were dragged kicking and screaming from a protest march ahead of President Obama’s arrival in Havana on Sunday.

More than 50 anti-government protesters were arrested at the Damas de Blanco (Ladies in White) demonstration as the Castro regime cracked down on dissidents ahead of the president’s visit.

The protest group holds a weekly rally outside a cathedral in an upmarket neighborhood of the Cuban capital, with hundreds of women and their male supporters calling for an end to political imprisonment in the communist state.

I chat with Cuban-American and conservative talk show host Silvio Canto Jr. often, who noted the Castro brother antics involving the Ladies in White ahead of the recent papal visit. Canto Talk’s next show will focus on the Obama visit as seen through the eyes of Cuban Americans. The normally effusive host finds it hard to express his disappointment:

“Obama’s statements about Cuba’s gains on education and health care were [during the press conference] were awful. Obama giving the Castros legitimacy is awful.”

Awkward and awful…so Obama’s ending his presidency pretty much as he began.