Timing is everything on reality TV, even more so when you start playing on the back foot. That was the case for James Andre Jefferson Jr., as the stand-up comedian got placed near the end of the lineup on The Circle season 3. But despite the disadvantage, James took advantage of his social skills, common ground, and an incredibly split group to take power quickly. And though he entered the finale down in the numbers, it was the numbers that worked in his favor, as he was ranked in the top spot across the final five players and claimed the $100,000 prize as this season’s winner. James didn’t enter The Circle until halfway through the season. But he hit the ground running–even though he couldn’t go anywhere–making a quick bond with Keisha “Kai” Ghost. He also fired up his catfish radar, focusing (correctly) on “Jackson” (aka Rachel Ward) and “Isabella” (aka Sophia Layne). His lack of trust in them put him firmly in Camp Kai, and his side put him in the influencer role alongside Nick Uhlenhuth two times in a row. On paper, it would be a stalemate as the two major alliances lock horns. But when push came to shove, James negotiated for Kai’s safety in exchange for getting rid of his other allies Daniel Cusimano and Jacki Jing. But ultimately, the strategy to pare things down to a tight inner circle worked to James’s favor. While Nick’s allies threw him at the bottom of their final ratings as a threat, his loyalty to Kai and Nick, as well as key personal connections with people like “Ashley” (aka Matthew Pappadia), won out in the end, making James’s dreams come true of supporting his grandmother and proposing to his long-time girlfriend. Read on to hear James’s thoughts on his time in the game. And check out Parade.com throughout The Circle season 3 with the various players and catfishes alike. What made you decide to enter The Circle? So my girlfriend and I–fiance now–watch Big Brother a lot. And we started watching the Netflix reality shows like Love is Blind and Too Hot to Handle. I told her to check out The Circle and let me know what she thought. And she told me, “No, we’re not going to watch it. It’s kind of whack.” So one day, when I was bored as hell, I watched the first episode and fell in love with it. And she fell in love with it after we started getting into the second episode. And after it was all done, I literally got onto Facebook or Google Ads, and it said they were looking for people to audition for season two of The Circle. I just sent a video in and got a call about a week later. Did you ever debate going in as a catfish rather than yourself? The problem is I wouldn’t be able to be anybody else! I would struggle with something like the whole Vince twist. Vince would have been a ghetto ghost hunter if I was him! There was a point in time I wanted to go in there with my girlfriend. That didn’t work out, but it would have been fun. So, of course, I have to wish you a massive congratulations on your win! Were you surprised to see you were the one that ranked at the top? Mike, I can’t tell you how shocked I was. I blocked Daniel from my alliance, and then I blocked Jacki from my alliance. After I blocked Jacki, I had a sense of comfort. Not that she needed me, but one of my goals was to get Kai and me to the end. I for sure thought me and Kai would be fifth and fourth or fourth and third. And when I see Nick, take the fifth-place position. I can’t tell you how shocked I was. I’m probably still more shocked at that than me winning. But when I actually won, there were about five to seven seconds I don’t remember because I blacked out a little bit. (Laughs.) I remember when I woke up, I almost fell over. I had to reach over at the table. My face looked blank because I wasn’t computing at all. What were your final ratings of the other four players? Kai was number one at all times. My process was who I wanted to win. So I wanted Kai to win first. Second was Ashley; Ashley and I had a great bond. After that, I got a little strategic. I thought Nick had a really good chance of winning. That’s why I put him last. Unfortunately, Sophia and I didn’t get a chance to really bond on the show. Because I came in late, there really wasn’t a lot of time to talk. So I put her third because I thought Nick had a better chance. You talked on the show about how you would spend the $100,000 if you won it. What have you been able to do since winning the season? My goal was to use the money that I got from The Circle to change the trajectory of my family. You could take $100,000; you could buy a bunch of things. You could buy a bunch of iPhones and go to Red Lobster 30 times. But if you do it like that, it’s not going to work. Most of the winnings, I still have. I bought a very modest car, a Ford Fusion. Because I had a 2002 Nissan Altima there that over 200,000 on it. (Laughs.) I do want to purchase property out here in California, but the housing market has been horrible. I got my girlfriend–my fiance now–a beautiful ring. It’s probably better than the Queen of England’s! You mentioned before how close you and Kai were. What made you decide to seek her out as your number one ally during your time in The Circle? They gave me an opportunity when I first came in to start a chat and bring one person at a time. When I saw Kai’s profile and her bio, I knew it was authentic. My entire life, from elementary school to my fiance to my niece, I’ve trusted Black women. I grew up with them; they’ve been around me. Without Black women, I wouldn’t be the person I am today. So when I see her, I have to trust her the most because that’s where my heart went. You and Nick went head-to-head several times, specifically in the last two influencer chats. How do you look back on those interactions? In-game, I loved Nick. At my heart, I’m a competitor. I did not have a problem with Nick. Nick made it fun for me. I love that you had these two alpha males that were in tears at the end. The competition was so fun for me. I’m the type of person who would sit down at the table and play Monopoly for 45 hours until I win. Unfortunately, going through the influencer chats both times, Nick was able to convince me. I like Nick because he made it fun for me. I woke up thinking, “How can I beat Nick today? Nick has to lose.” Let’s focus on that first chat, where Nick convinces you to get rid of Daniel. What made you decide to block him, despite him being part of your alliance? My mindset going into that influencer chat was to keep Daniel. I want to preface that by saying before I had the conversation about “Viva La Resistance.” I didn’t even know it had a name until Daniel told me after! (Laughs.) I didn’t know where Daniel stood. I always had a weird feeling about him being too nice to everybody. When the alliance started, it was pretty much us three versus those three with Jacki in the middle because she couldn’t be blocked. When I went into the influencer chat, of course, in my head, I already knew Nick was going to keep Isabella. And Nick knows that I’m keeping Kai. So at that time, I knew it was either going to be Ashley or Daniel. Nick gave me some information that turned out to be false information he got from Jacki. And he said that Daniel gave him that information. So with that, combined with the fact that I didn’t have trust for Daniel, it made it a little easier. Now I knew I was going to piss off Kai. I literally lost sleep that night, not because I blocked Daniel but because I pissed off Kai. And that also gave me a chance to talk with Kai and get my reasoning on why I did what I did. One of your more memorable moments of the season was when you opened up to Ashley about your trans brother. What made you decide to reveal that information? I’m a comedian, first and foremost. I open up my life regardless of people. I talk about my relationship; I talk about tragedy, I talk about racist things that I’ve been through. So opening up to an individual is actually easy. I’m always telling my story. Finding that person to open up to was not difficult because of who Matt portrayed himself as in the game. I related to Ashley because I thought Ashley was the funniest person in the circle. If you ask me to vote again, who was the funniest person, I would say Ashley. Ashley was one of the people that made me actually laugh out loud in The Circle. So when I had that conversation with her, she really represented the LGBT+ community very well. I just wanted to let her know, “Hey, I’m rocking with you.” You made it clear that you thought Isabella was a catfish throughout the season. What was it that put up such red flags? So there was a message Sophia wrote; I can’t remember what it was. I remember thinking, “She’s being careful.” I think the catfishes in The Circle are the most careful. They have so much to worry about. They have to remember their secret identity and themselves and what they said to this person and that person. I didn’t have any hard detail; it was mostly a feeling. And I went with it and stayed with it, and I was right! (Laughs.) How much did coming late into the season change our initial strategy? I can’t tell you how much it changed! I had a strategy to come in as everybody’s uncle and just have a good time. I was actually after for season two; seasons two and three flew out together. When I didn’t make season two, I was kind of beat. My fiance told me, “It’s okay. If it doesn’t work out, it doesn’t work out.” Everyone on the season got a phone call around 6:00 p.m.I got a phone call at midnight. I think somebody else was supposed to come in. I think I was a last-minute decision to this day. And it worked out! But I remember once I found out I was going in, I just wanted to have a good time and be myself. Did you learn anything about yourself during your time in The Circle? I’ve kept myself around a certain type of people because of how I’ve grown up. Being with this group of people, every single one of them I have a relationship with. Before the show, I would never kicked it with somebody like Nick. I [expletive] love Nick now. What I learned is don’t judge people. You could find a relationship with anybody, regardless of gender, sexuality. I guess I stopped doing the thing that the show’s about. I stopped judging a book by its cover. Next, read our interview with Calvin Kiing Crooks, who was eliminated in The Circle Season 3, Episode 7.