When US president Barack Obama flew to Cuba to re-establish diplomatic relations, Ben Rhodes was also there as one of the key negotiators.
Rhodes, the deputy national security adviser for strategic communications, first started working with the Obama campaign in 2007 as a speech writer.
Over the years, he became a significant voice, not just in crafting the message, but in actually shaping US foreign policy. He was the man who directed the media operation to sell the Iran nuclear deal to a sceptical American public.
Russia poses this immediate threat to kind of international order and stability. China is a much more powerful country and is much more positioned to be a competitor to the United States in a way that Russia can't.
Some believe that, while he doesn't think for the president, he knows what the president is thinking.
As he now prepares to leave the White House for an incoming administration, it is clear that Ben Rhodes - as he talks to Al Jazeera - is not ready to stop thinking about the future of US policy.
Asked about the Afghanistan war, Rhodes doesn't believe it was a mistake for the US to scale back their presence there and give it a timeframe.
"We had to scale back. And frankly, the American public had an expectation that we were going to scale back. And you know, sustainability has always been a concern of the presence on our counterterrorism and war efforts ... He [Obama] didn't want to leave his successor, for instance, with what he found - which was 180,000 troops in this massive resource allocation," Rhodes says.
We ask Rhodes whether Obama didn't want to commit the same level of resources, and had considerations about sustainability and what his successor would inherit in the back of his mind, when it came to the Syrian civil war.
"It was part of it," Rhodes says. "I think another part of it, that is less fully understood and appreciated, is that he never felt like he saw a military option that worked."
In Syria, Rhodes says, "there was never a military option that he could see beyond the first move."
We ask Rhodes whether Obama made a mistake to issue a red line after the chemical weapons attack in Syria in 2013.
"I don't think so, for the simple fact that for all the messiness of that, that did lead to the removal of a lot of chemical weapons," he says.
We also discuss Russian "aggression" particularly against Crimea and its neighbours, its role in Syria and Russian hacking during the 2016 presidential election.
When it comes to US security policy in the long term, Rhodes says "China is going to be a much more powerful country than Russia".
He says in the immediate future, geopolitically, "Russia poses this immediate threat to kind of international order and stability. China is a much more powerful country and is much more positioned to be a competitor to the United States in a way that Russia can't."
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Source: Al Jazeera