This was the first time we had woven together all the different threads of criminal justice reform. Our audience was both Democrats, who are likely to see this as a moral issue, and Republicans, who are likely to see this as an issue of fiscal conservatism—why are we spending all this money keeping nonviolent offenders locked up when we could spend it on schools or roads or bridges instead? One of the things that I’m very proud of about that speech is that I think we managed to combine those arguments so they flowed together seamlessly. And we also were able to combine argument and policy detail and story, and that’s what you always hope will happen with the speech.

The other speech I’m really proud of was helping to bring Luther the anger translator, played by Keegan-Michael Key, onstage with president Obama for the [White House] Correspondents Dinner.

[I was proud] not just that it was funny, which it was, but that we included the part where president Obama got legitimately angry about climate-change deniers in Congress and Luther the anger translator tried, and failed, to calm him down. So we were able to include a serious message about an important issue in something that we knew lots people were going to see, because it was funny.

I remember watching the speech with Luther the anger translator and thinking, “That was pretty ballsy.” You were taking something that poked at racial prejudices and turning them into humor around the president. And though that was towards the end of his term, it felt to me like a risky thing to do. Did it feel risky?

It didn’t. It felt right. We had thought about it in other years. President Obama was already a big fan of Key and [Jordan] Peele and he liked the Luther character. [In previous years] it never felt right. But 2015 was the year where we were kind of saying “bucket”—you know, one of Obama’s jokes was, “After the mid-term elections my advisors asked me, Mr. President, do you have a bucket list? And I said, I have something that rhymes with bucket list.” There was a sense that with the midterm elections behind us, we were going to do the stuff that felt right and worry a little less about all the other things that get in the way. I think that’s why bringing in Luther the anger translator just made so much sense.

Obama spoke last week on the sidelines of the UN general assembly, and said, “Your response [to difficult challenges] has to be to reject cynicism and reject pessimism and push forward with a certain infectious and relentless optimism—not blind optimism…but a hard-earned optimism that’s rooted in…stories of very real progress.” That optimism certainly comes across as one of his defining characteristics, but was he really that optimistic? And why do you think it was?

I think the kind of optimism that I found so attractive in president Obama as a candidate, and that I think really infused his White House, was, as he said, not blind optimism but an optimism rooted in perseverance. The idea that over time, if we do the work, things will get better. That’s different than saying, “Tomorrow is going to be better than today, just because.” It was the sense that if we do our part, other people will do their part. And we might take two steps forward and one step back, but in the end we are going to make progress, and that’s more nuanced than politicians often get.

But I also think it was borne out by many of his greatest accomplishments. They were things that almost didn’t happen or took longer than some of our supporters would have liked, but we’re seeing now many of those achievements turning out to be harder to undo than Republicans and president Trump thought initially. And one of the reasons, I think, is because they were the product of not just seizing the moment when the moment appears, but of doing the work every single day to build those moments and create those opportunities.

Do you think Obama attracted optimistic people to him, or did he make those kinds of people? Did people come in as pessimists and leave as optimists?

I think it’s both. One of the interesting things about the Obama White House and Obamaworld is that the people who ended up there were not people who necessarily thought they were going to be in politics from the moment they were 10 or 12 years old. It’s often people who felt like they wanted to be part of whatever the most important thing was. And what president Obama was able to do was make the case that that thing is politics.

I think that’s going to have a ripple effect, because you have all of these people—I’m certainly one of them—who did not think of themselves as political people but now say, “You know what, there’s no better way to make an impact.” I hope that down the road we see changes in our politics because of that.

The other thing, that I do write about in the book, is the fact that president Obama was persistent. I certainly was not the kind of person that always said, “Well, this is going to work out.” There were moments when I really wasn’t sure and there were moments when I wondered whether president Obama was right to have that sense of optimism. And I’m happy to say that in every instance I found myself looking back and saying, “Man, president Obama was totally right.”

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