WASHINGTON D.C. - President Obama has moved to cut deals in recent weeks with two enemies of long standing. On Tuesday, the administration said it would take Cuba off its list of state sponsors of terror, a couple of days after Obama shook hands with President Raul Castro at the Summit of the Americas in Panama. This after the administration reached a tentative nuclear arms control pact with Iran.
It was all reminiscent of a pledge Obama made back when he was first running for the White House. In response to a question posted on YouTube, Obama said at a 2007 debate that he would be willing to meet in office with leaders of countries such as Cuba, Iran, Syria, Venezuela and North Korea.
"I think it's a disgrace that we have not spoken to them," Obama said at the time. "The notion that somehow not talking to countries is punishment to them... is ridiculous."
He was widely lambasted, not only by Republicans but by his future Secretary of State Hillary Clinton. "I thought that was irresponsible and frankly naive," she said.
Today, as a presidential candidate, Clinton faces a tough choice in terms of how closely to embrace Obama's outreach efforts. One Clinton ally has hinted she'll oppose the Iran deal.
"She will be put in the very difficult position of saying either she supports it, or doesn't support it," says Rajan Menon, an international affairs expert at the City University of New York. "In both cases, it's a problem."
For their part, Republicans believe Obama is selling the country out, making bad deals with dictators. There's nothing wrong with engagement, but Obama has undermined the nation's security, says Danielle Pletka, senior vice president for defense and foreign policy studies at the conservative American Enterprise Institute.
"There's a difference between engagement and slavishly sucking up to bad people and abandoning your friends," she says.
It's always easier to make deals with friends - even ones you've pissed off, like, say, Israel - than it is with enemies. Keeping your enemies close, or at least untangling the worst knots in the relationship, can ultimately serve a greater purpose than continuing to make nice with countries you have no problems with anyway.
Obama believes he's broken historic logjams in ways that make sense for America. That remains to be seen. Polls in recent months indicate a majority of Americans support his decision to open up relations with Cuba.
In terms of Iran, members of Congress have made it clear that they'll want to sign off on any final nuclear pact. That dynamic suggests "even his fellow Democrats believed he had overreached in trying to operate on his own," writes The New York Times’ Peter Baker.
Obama's maneuvers are in keeping with two different traditions. One is the freedom second-term presidents often feel as they look abroad to make their mark. Especially when, like Obama, they've lost the ability to work out any deals at home.
"Since the November elections, they've really doubled down on this engagement thing," says Brian Katulis, a senior fellow at the Center for American Progress, a think tank with close ties to the administration.
The second tradition is the very idea of reaching out to previous pariahs. Richard Nixon inspired an enduring cliche by becoming the communist-basher who went to China. Similarly, the old Cold Warrior Ronald Reagan found that Mikhail Gorbachev was someone he could do business with as the Soviet's "evil empire" was starting to crumble.
Obama himself cited Reagan's example during the 2007 debate. But the president’s moves lately have been even gutsier, Menon suggests.
Nixon and Reagan were both taking advantages of opportunities that presented themselves on the world stage, he says, whether it was exploiting the rift between China and the U.S.S.R., or Gorbachev's policy of glasnost, or openness.
Obama's deals may be controversial, but he chose to carve them out as possibilities for himself.
"Here, he's not seizing an opportunity, he's making engagement on his own," Menon says. "In that sense, it's even bolder."
Perhaps Obama is still trying to earn that Nobel Peace Prize he won his first year in office.
Want to keep up with all the latest DecodeDC stories and podcasts? Sign up for our weekly newsletter at decodedc.com/newsletter.