Is Phillip Sheppard a character, or was he merely playing one when he appeared on Survivor: Redemption Island? Walking around in pink undies and an occasional feather on his head, Phillip acted crazy and often drove his tribemates equally nutty with his behavior — which included mispronouncing one of their names and complaining about a lack of burnt rice. But the player insists that it was all a well-designed ruse to get him to the end of the game, and get to the end he did thanks to Boston Rob. Now, Phillip is back as one of the familiar faces returning for Survivor: Caramoan — Fans vs. Favorites (premiering Feb. 13 on CBS). What sort of hijinks does he have planned this time? How does he feel about being reunited with Fransesqua…uh, I mean, Francesca? And what is this about a new book he wrote based on his island alter-ego? (You can even hear an audio file of him reading from the book below! And trust me, you need to hear it.) The former federal agent (maybe) told all when we spoke last May just days before filming began.
ENTERTAINMENT WEEKLY: Greetings, Specialist. First question right off the bat: What are you going to do if someone on your tribe tries to take the last scoop of the crispy? Not on your watch, right?
PHILLIP SHEPPARD: That’s right. That’s not gonna happen. If anyone were to take that last scoop of crispy, I don’t know what I would do.
EW: And I think the other question that everyone is gong to want answered with you coming back is what kind of underwear do you have picked out for this season?
PHILLIP: I only know one color of underwear.
EW: Okay, so pink it is! Tell me why you’re going to win this time. You made it to the end last time but couldn’t seal the deal.
PHILLIP: Well, one of the reasons why I think I’m going to win this time is that I’m actually going to get a chance to establish myself with the players early on. As you know, Boston Rob came out of the door saying “I own this season,” and he never looked back. I had to figure out a way to get close to him in a way the other players couldn’t. This season, I think there’s a very good opportunity with people like Cochran, and Andrea, Corinne — I like people who work hard. As far as the ladies I could easily see myself getting with Andrea, Corinne, I saw Dawn Meehan is here. I think I got a shot with those people. In terms of the men, Erik is kind of a wild man because of the way he went out the last time. I’ll tell you what you won’t see. You won’t see me have the big blow-ups. You’ll still see me have situations where I think if it is going to serve a purpose, like at Tribal Council where I might do something colorful. But in general, my demeanor is going to be slightly different, but fun and entertaining at the same time. Because I am going to be wearing something unique in my undergarments as well as my shoes. That’s a clue!
EW: What did you learn last time that is going to help you the second time around?
PHILLIP: The number one thing is I learned from Boston Rob that you have to have a one-on-one relationship with every single person out there. They have to feel that you have a general interest in what they’re about and who they are. And they have to actually like you. So I have to create some form of likability factor in pink.
EW: We met the Specialist last time you were on. Is there a new persona you’ve cooked up for season 26?
PHILLIP: Actually, you guys met the Specialist, but because Boston Rob was the Mentalist and the Mastermind, the Specialist did not emerge as the Mastermind, so the Specialist needs to get promoted in this game. He needs to become the new Mentalist of the game.
EW: I don’t really know what that means, but is there anything you have planned to combat any possible “dry mouth” you may experience back on the island?
PHILLIP: Hopefully the Tribal Councils won’t go on as long as that one did. You only saw a three minute clip. That thing went on for, like, three hours. And Francesca, by the way…
EW: HEY, YOU SAID HER NAME RIGHT!!!
PHILLIP: That’s what you don’t know. She says it, but they didn’t show it. She said, “You can say my name. You’ve been saying it right all night.” It was only when I got angry with her that I decided to come up with something else. I said it by mistake at first right after that dry mouth. I went “Francesqua.” And I saw her reaction on her face and the way that she said “My name is Francesca.” And I decided, I’m going to keep doing that. I could always say her name, Again, that’s a strategy that nobody realized, that I deployed. It was very effective.
EW: Well, you see her here. She’s coming back. You’re coming back. What’s your strategy in terms of dealing with her again?
PHILLIP: She’s going home. I know my gut and I read people right their first time. And I remember looking at her video clip on the website when they announce the cast and have their first web video and she says she enjoys torturing girls in school. When I saw that after I got back home, I went, you got it right buddy. This is a different person. She’s a grown person talking about how she liked torturing girls in school. So I thought, okay, you made the right call. So it would be really cool if I thought we could go out there and play together, because it would surprise everybody. But I don’t see it happening. I think her sense of payback is probably great within her and she couldn’t overcome that and do the logical thing, which would be to make it appear like she really disliked Phillip and then get together and we could take over this game Now that would be awesome. But I don’t see that happening.
EW: What about your other former castmate, Andrea? What are your feelings on working with or against her this time out?
PHILLIP: Andrea is someone who is totally predictable, and in a good way. She’s a hard worker. She’s a real competitor. If she’s really willing to take my lead this time around, I think she’ll go far with me in the game. I could easily see her and I going all the way. If she can really listen and do what I tell her to do in the game, I think she can go very deep in the game.
EW: Did you have any hesitation to coming back to play? I know there was talk of you coming back for the South Pacific season and that didn’t happen. Tell me your whole thought process in coming back to play again.
PHILLIP: Everyone said, ”It would be a great season to see you and Coach come back and play.” I never got behind that idea. That didn’t really intrigue me. I also wanted to give it some time for me to completely heal — physically, mentally, emotionally. Because I went through what I call a two-step process: One is playing the game, and then there is coming back and having everybody say, “He’s crazy, he’s crazy, he’s crazy,” and as you know, I was ubiquitous. I was everywhere from the E! to The Soup! To everywhere. I was in Entertainment Weekly!
EW: Damn straight, you were!
PHILLIP: I loved it by the way, but at the same time it was kind of tough to deal with. And then I took a step back and said, “This was kind of big. You need to let the audience settle down and let them want you back.” Now we’ll have the equivalent of three seasons passed. It’s perfect timing. I always wanted to play on a season where I get to see people — they know me, and as a federal agent you know I do thorough homework, and you can bet I’ve studied every one of these people potentially returning from the seasons that I previously watched before. So I feel like I’m ready to come out and play the game — looking like the same guy, but playing a very different game. The challenge or me the first time was to see if I could put something on display and sustain it for 39 days. And I did and it got to the end — first runner-up. And I want to see if I can do that again, and walk away with a million dollars.
EW: What have you been up to since we last saw you on the island?
PHILLIP: I’m in the process of writing a book called The Costa Rica Job. You can read the first 13 chapters online at phillipsheppard.tumblr.com. It’s a blend of me. The character is called The Specialist. He’s working a job in Costa Rica, he’s a former federal agent, and he’s sort of a James Bond like character. I’m looking for a publisher right now. I just completed the book. [Ed Note: The book will be available on Feb. 12, and you can — make that MUST — hear Phillip read a passage from the book below!]
EW: Well, I can’t wait to see the footwear, the underwear, any kinds of “wear” — it’s exciting stuff.
PHILLIP: Let me just give you one clue on the footwear. I did something wrong. I said “the shoes.” You know how they have us start off in our everyday regular outfit? I’m coming back with something very special in my sneakers. I can guarantee you they are going to talk about the sneakers I’m wearing the way they talked about the underwear.
Phillip Sheppard reads from The Specialist: The Costa Rica Job:
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