There's the president of the United States, and then there’s the person who happens to be the President of the United States.

Bill Clinton served for eight years, but we were always more intrigued by Bill Clinton the Person—a magnetic charmer once described by Chris Rock as “a cool guy, like the president of a record company.” Clinton’s charisma defined his presidency, for better and for worse. He couldn’t always harness it. He couldn’t stop trying to win everyone over, whether it was a 60 Minutes correspondent, 500 powerful donors in a crowded banquet hall, or a fetching woman on a rope line.

If Clinton acted like someone who ran Capitol Records, Obama—both the person and the president—carries himself like Roger Federer, a merciless competitor who keeps coming and coming, only there’s a serenity about him that disarms just about everyone. At one point during the hour I spent interviewing him at the White House this fall, he casually compared himself to Aaron Rodgers, and he wasn’t bragging. Obama identified with Rodgers’s ability to keep his focus downfield despite all the chaos happening in front of him. That’s Obama’s enduring quality, and (to borrow another sports term) this has been his “career year.”

Obama lives in America’s most famous museum and uses it to his advantage. You’re sitting there in some ancient tearoom waiting for him to show up, surrounded by portraits of former first ladies and framed maps from battles that America won over the centuries. Everyone is friendly but suspicious. Everyone talks in hushed tones. You feel like you’re intruding at all times. You’re just…waiting. Suddenly, ten anonymous security guards pop out of hallways and doorways that you didn’t know were there. The energy shifts. And then, there’s Obama—big smile, big handshake, some ball-busting comments to put everyone at ease. Within seconds of greeting me, he was poking fun at my shoes and teasing me for not writing anymore.

“It’s really aggravating not having you on Grantland,” he said, almost like I betrayed him. “I go to the site and there’s no Simmons. Come on, man, it’s not the same.”

“It’s really aggravating not having you on Grantland,” he said, almost like I betrayed him. “I go to the site and there’s no Simmons. Come on, man, it’s not the same.”

It’s an alpha-male trick—put someone off-balance, flatter them and bust their chops at the same time. A few minutes later, he was grabbing control of the interview with measured responses, knowing that he didn’t have to perform without cameras or podcast equipment. And so he took his time. And it worked. I mean, how do you interrupt the most powerful man on earth? It felt like the way Federer repeatedly jumped Novak Djokovic’s second serve in the 2015 U.S. Open Final—a savvy trick to disrupt someone’s flow, a seemingly harmless way to gain an edge. It’s what the great competitors do.

In January, Obama will begin his eighth and final year on the job. It’s an era now. What has he learned about leadership? What was his biggest regret? Why did it seem like, in 2015, he finally started letting it fly, threw on his Beefsquatch costume and let everyone know “THIS IS ME NOW!” Gay marriage, health care, Charleston, the Iran deal… If you voted against him, 2015 was the year when his inner confidence bothered you more than ever. And if you voted for him, 2015 was definitely the year when you said, “That is the guy I voted for.” But what if Barack Obama has been that guy all along?

BILL SIMMONS: If you could go back to 2008 and tell yourself one thing, what would it be?

BARACK OBAMA: “You’re going to be busy.” Coming in, we were going through an unprecedented economic upheaval, combined with an upheaval in the Middle East that we hadn’t seen in our lifetimes. There was going to be a huge amount of disruption. I would probably tell myself to communicate more effectively early on than I did. We ran a great campaign. It wasn’t as great as it seems in retrospect—there’s always rose-colored glasses but there’s no doubt that we captured the country’s imagination. And somehow in those first two years, I think a certain arrogance crept in, in the sense of thinking as long as we get the policy ready, we didn’t have to sell it.

One thing I learned through some tough election cycles: You can’t separate good policy from the need to bring the American people along and make sure that they know why you’re doing what you’re doing. And that’s particularly true now in this new communications era. I think that we were ahead of the curve in 2008 in social media and the Internet and digital communications. When we came into office, instead of taking some of those lessons, we suddenly adapted ourselves to the White House press room and structures that had been built back in the 1940s and ’50s. As a consequence of those missteps early, we got the policies right, and that’s why the economy now has grown for five and a half straight years, six years, and why unemployment rates have gone from 10 percent to 5.1 percent. But there was a lot of political pain along the way that might not have been necessary.