Lutki Gayop can't talk about November 2008 without nostalgia rippling through his voice. It was a bold month for him and the nation. In the middle of the Great Recession, he both voted for Barack Obama and opened a business, a women's clothing boutique in Hoboken, New Jersey. "I'll never forget it man," he told me. "It was right when the economy crashed when we decided to open the first location, and it was our baby."

By the time Obama was campaigning for reelection in 2012, Lutki had opened a second store in the Soho section of Manhattan with his business partner, a former girlfriend. He also voted for Obama a second time in 2012 and has no regrets. "I would have voted for Obama for a third term," Gayop said.

But when I asked him if he would have voted for Obama against Donald Trump in 2016, he paused to revise his answer: "I can't say that I would. Can't answer that. I don't know. I would have to see the two of them campaigning. I would have to see it, the campaign."

Gayop, the son of Haitian immigrants, grew up in the Flatbush section of Brooklyn and is part of a key block of voters: people who cast ballots for Obama before going for Trump last year. According to the American National Election Study, 13 percent of voters who cast ballots for Trump also voted for for Obama in 2012, while only 4 percent of Hillary Clinton's support came from 2012 Mitt Romney voters. Obviously, many of these voters have views that do not neatly fit into the boxes of left and right or Democrat and Republican. Why else would someone support both the country's first black president man who sought to undermine him through the absurd birther conspiracy?

These swing voters have been analyzed extensively by journalists and pollsters after their presence in swing states like Pennsylvania and Wisconsin likely swung the election. I interviewed many of them myself in November. One of the intriguing things about them is that they present an opportunity for Democrats: If Obama got their vote, potentially so could another liberal candidate. A survey from earlier this year found that Obama-Trump voters were more likely than other Trump supporters to regret their vote and disapprove of Trump.

My own follow-up interviews with these voters bear that out. Gayop told me that Trump has disappointed him on immigration and his appalling both-sides-to-blame reaction to Charlottesville. That sentiment was echoed by his fellow Obama-Trump voter Warren Rogers, who owns an energy investment firm in London and admits his vote was a mistake.

"A good characteristic of anybody is to admit when they're wrong," said Rogers.

Despite his vote, Rogers can sound like a member of the anti-Trump resistance. "Honestly, I don't understand how it could be worse. When he started filling his Cabinet spots with his family, and then when he evicted the FBI chief," he told me. "I view it as completely disrespectful to the process of democracy. I don't think you could have handled the events of Charlottesville worse if you tried." But his support of the real estate mogul was never full-throated, he added: "I was never super comfortable with my vote for Trump. I viewed myself as not voting for Hillary. I viewed myself as somebody who could support Mike Pence, and the way it's going now, we'll be getting a lot more Mike Pence maybe, if we could be so lucky."

Unlike Rogers, Gayop is still bullish on Trump. While he gives the Trump presidency a C+ so far, he hopes and even expects the grade will rise with time. "Giving up on Trump is like giving up on America, " he said. "I like that Trump is on the side of capitalism. Ever since I was a kid, I always followed Donald Trump as a New Yorker... Certain things that he says are kind of out of line, but he also says a lot of the things that I want to hear. Trump comes out whichever way he feels and puts out whatever is on his mind. I like honesty."

John Sides, an associate professor of political science at George Washington University and research director of the VOTER Study Group, which has studied these voters, said that they often have a "weaker connection" to the Republican Party than Romney-Trump voters. They're "a little bit more likely to be Democrat than Romney-Trump voters and more likely to now disapprove of the job Trump is doing than Romney-Trump voters."

Mike Alberta, a union electrician in Hawthorne, New Jersey, is a case study in how a Democrat could vote for Trump. He was an early fan of Obama in 2008 for his stance on labor issues. After Obama won, Alberta was such a fan he stopped watching FOX News because he was turned off by the negative coverage of the president. He voted for Trump because he disliked Clinton, and has now stopped watching CNN because of what he sees as the network's bias against the new president.

"I check the headlines to see what the major stuff is every day, but I don't watch FOX News or CNN—they both choose sides and favor one or the other, and I'd rather hear a neutral thing," he said. "And I'm not so much about the party aspect. I'm more for the person than political party. I don't like that Trump has backpedalled on a lot of his promises when he was campaigning, like how he was going to be for the construction industry and all that stuff. I feel like he hasn't really jumped into that yet. But I like to give everyone a chance for a little while. I mean listen, he came in as president, he's never done this before, he's never had much political experience. He's been there eight months, and it's hard to accomplish things with everyone against you. It was the same for Obama... I like to hope that in time he will do some good things for us."

If many Obama-Trump voters share Alberta's views, it may take time for them to turn against Trump—but it could happen before 2020. In the meantime, it's unclear if these people will have as much sway in 2018.

"It is an open question whether Obama-Trump voters are going to show up in the midterms," said Sides. "Partisanship is extremely powerful in midterm elections. Right now, our research shows that Obama Trump voters are more likely to be uncertain about how they're going to vote in 2018 than Romney-Trump voters. So it may be the case that they're not as mobilized or motivated to vote or they need an extra nudge to get out there in the midterm."