Jonathan Young Details Emotional Letter Boston Rob Wrote Him Before 'Survivor 50' (Exclusive)

When Jonathan Young last played Survivor four years ago, he spent a lot of time catching fish and winning nearly every challenge, but he ultimately walked away without the million dollars after falling short in the Final Four fire-making challenge. Now, as he prepares for the milestone 50th season, he’s coming in with a very different mindset—and a little help from a legend.

For the last three years, the Alabama native, 32, has been quietly "sitting at the feet" of former winner Boston Rob Mariano. The two became close friends after Young’s first season, and just before he left for Fiji this time, Rob handed him a letter with a strategic breakdown of how to handle this returnee cast.

"I’m going to get emotional," Young told Men’s Journal while discussing the letter on set before the game. "He’s my friend. He said there are three things that you need to remember. No. 1: Smile. Nobody wants to play with somebody that’s in a bad mood. No. 2: Try to see the game through your opponent’s eyes. And the third one is you can only control what you can control. Don’t worry about the rest."

Young is also navigating a unique spot in the cast as the only person from his season—and the only one from the first four seasons of the new era. While other players have former allies or cast mates at Ponderosa, Young says he's a total free agent. He's already keeping a close eye on the "old school" legends, the winners, and even the "Swifties" (Sorry, Charlie.)

"I can milk that all the way home to the finale," Young said of the massive targets. "There’s a million things I can point my finger at and go, 'Look at them, not me.'"

Below, Young talks more about that letter from Rob, the not-so-good vibes he's picking up from players like Aubry Bracco and Charlie Davis, and why he’s actually glad the editors hid his strategic game the first time around.

Men's Journal: So has Survivor been something that you definitely wanted to do again after your season?

Jonathan Young: As soon as I left, I knew I wanted to play it again. Yeah, as soon as Mr. Jeff [Probst] called me, I said yes. I had an opportunity to be on American Gladiators, but it filmed the same time as this. And I said wholeheartedly, I’d rather do Survivor. I don’t know what it is. I guess it’s because it’s real. I mean, it’s the real deal. There’s nothing about this that’s fake, and that makes me want to do it again. I learned a lot the first time I was out here about me.

Men's Journal: Do you feel like you have unfinished business?

Jonathan Young: I think the first time I played, I really fought the good fight. I think I left it all on the island. But I think that this is a whole other adventure. Aside from that, this is something different. I’m not looking at things I didn’t do that I wish I would have done, because I really felt like I did everything I could do. But what I am going to do is change my game in certain ways. For example, I’m going to look through the opponent’s eyes a little more, see what they see through their lens. I’m going to smile more. I need to smile more, that’s for sure. And you know, I can only control what I can control. I can’t control if there’s a tribe swap or if someone doesn’t want to work with me. There’s only certain things that I can worry about. This whole game can be very, very anxiety-ridden if you let it be.

Men's Journal: Who are you looking to align with?

Jonathan Young: I’ll work with anyone that wants to work with me. I’m the only person out of the first four seasons of the new era. And, I mean, honestly, there are a few people that I want to work with, like Miss Stephanie [LaGrossa Kendrick]. I think she would be great. I like her a lot; I’ve met her at a fundraising event. Even Colby [Donaldson], [Benjamin] Coach [Wade]—I like all of them because there’s a lot of big names out here. Ozzy [Lusth]—I’d work with him, but he’s a big name, which is great for me. He’s the OG challenge beast. So I don’t think I’m as big of a target as I was in Season 42. Yes, I’m big, but these people have been On Fire with Jeff Probst. They’ve won. We’ve got winners. We have people that have played with two to four other people. Most of them have played with somebody before; they’ve got that connection. I’m a free agent. I don’t have that.

Men's Journal: What do you think about the fan voting? Do you want rice?

Jonathan Young: You know, I kind of want them to not give us rice, because they’ll need me more. Provider—that’s kind of my role, and I have to somewhat keep up with that because they’re expecting it, you know?

Men's Journal: I was going to ask, are you going to play a similar game to last time or do you want to switch it up?

Jonathan Young: I’m going to change it a little bit, for sure. I think that with us all being returning players, there’s a lot of room for pushing the vote onto someone else. I mean, Cirie [Fields] just won Traitors, and she’s a Survivor legend. These people that are playing are some of the best, and I can milk that all the way home to the finale.

Men's Journal: Are you very much aware and keeping an eye on who has relationships, and who’s played with who?

Jonathan Young: Yeah. I mean, the winner, Kyle [Fraser]—we just saw him win a million dollars. The last thing we saw was him win a million dollars, right? And then Kamilla [Karthigesu] was right there with him, and they’re out here. You’re telling me they’re not going to work together? You see what I’m saying? And then Joe [Hunter], who was in third, who was kind of working with them. There’s a lot of that going around. You’ve got Q [Burdette] and Tiffany [Ervin] out here. A lot of people that have played with each other will want to work with each other, and I can use them.

Men's Journal: Are you picking up any vibes at Ponderosa? Any observations?

Jonathan Young: You know, everybody’s kind of looking at the [Season 49 players] a little bit. No one knows what they did or how they did. The devil you know is better than the devil you don’t. I think everybody’s kind of feeling that it’s a little eerie.

Men's Journal: Right. And they could technically not tell you what actually happened on their season. They can lie.

Jonathan Young: If they’re friends, why wouldn’t they? Most all the other people are friends. I mean, Heroes vs. Villains—there’s four or five people that played in that season. I have a feeling they’re going to want to work together, all of them.

Men's Journal: So, in terms of the new era, you’ve played in it, there’s tons of advantages and idols. Someone like Colby or even Stephanie hasn’t played in a while. Do you think you could bridge that gap since you said you wanted to work with them?

Jonathan Young: Absolutely, because I’m a free agent and I’m right in the middle. I’ve got nobody that was on my season or the season before. I have this opportunity where I can use that to work with the new school and the old school. I don’t think Colby will be used to the game. Colby is a pretty straight shooter, and I think that I can use that to my advantage.

Men's Journal: Anyone else you’re keeping your eye on?

Jonathan Young: I don’t know if I’m going to be able to work with Charlie [Davis] because I’m not a Swiftie. I don’t know anything about Taylor Swift, and we’re completely opposite from what I’ve gathered. But he’s really good at the game. No disrespect to Charlie, he’s great at the game, but you’ve got to have something in common, you know what I mean?

Men's Journal: So you didn’t listen to Taylor Swift to prepare?

Jonathan Young: No, I didn’t. I can’t name 400 songs.

Men's Journal: Well, actually, that’s a good question though. How did you prepare for Survivor your second time around?

Jonathan Young: I changed my workouts a little bit. But the main thing is I had a new friendship out of this from Boston Rob. He’s been a good friend for three years, and I’ve talked to him for three years. Listen, I sat at the feet of a legend, and I got to hear how he played the game and understand how he played the game—and not just that, but how he lived. I’m going to use a lot of what he taught me. It was a real honor.

Men's Journal: What kind of advice did he give you?

Jonathan Young: He gave me a letter before I left. It was—I’m going to get emotional. He’s my friend. He said there are three things that you need to remember. No. 1: Smile. Nobody wants to play with somebody that’s in a bad mood. No. 2: Try to see the game through your opponent’s eyes. And No. 3: You can only control what you can control. Don’t worry about the rest. If there is a tribe swap or if somebody does something, I can only control me.

Men's Journal: Smart. Speaking of those things, do you see people eyeing you at Ponderosa? What do you think?

Jonathan Young: Everybody wants to smile at everybody because you don’t want to throw anybody under the bus because the game hasn’t started. Everybody’s friendly to everybody, overly friendly—like a door, "let me get that for you"—but we can’t talk, so we have to be very careful. If somebody drops something, you want to be the first to pick it up. It’s like the game has already started. But when we hit the beach, Ponderosa kind of goes out the window. We don’t even think about it; we don’t bring it up. Now, everything feels so big because there are no words. We’re all super animated and none of us are talking.

Men's Journal: It’s got to be weird. Even seeing you guys walk around here, it’s so odd.

Jonathan Young: It feels awkward as heck. [Executive producer] Matt Van Wagenen, when I first played, I said, "Do you have any advice for me to win this game?" and he said, "Don’t get comfortable." That was really good advice because as soon as you get comfortable, you’ll get kicked out. You’ll be blindsided. That happened I can’t tell you how many times on my season—people get comfortable, like "I’ve got it figured out." As soon as you have it figured out, you’re out of here. And that’s another thing—they didn’t show a lot of strategy for me in my season, which will help me so much. At first I thought it was a curse, but it’s actually a blessing. They didn’t show barely any strategy for me because of my physical performance. I struggled with not getting any credit for my strategic play, but now I’m thankful. I’m glad they didn’t show it.

Men's Journal: Do you have a strategy going into the first few days ? Are you going to try to lay low?

Jonathan Young: The thing is, because I’m surrounded by a bunch of legends, I can lay low way more than I could the first time. Almost everybody else has done more than me. I played Survivor once. I wasn’t On Fire with Jeff Probst. I didn’t win. I don’t have somebody else with me. There’s a million things I can point my finger at and go, "Look at them, not me."

Men's Journal: Coming out of this game, if you don’t win, what do you want to take away from it?

Jonathan Young: I want it to be a memory where I don’t regret anything. I want no regrets. I’m going to play hard, and I promise I will.

Men's Journal: Anyone you really want or don’t want on your starting tribe?

Jonathan Young: I would love to have Miss Stephanie on my tribe. I really would. Who I wouldn’t want—is her name Aubry [Bracco]? I just—there’s certain people I don’t get good vibes from. Maybe it’s Ponderosa talking, but like Aubry and Charlie. I like Christian [Hubicki]; I’d like him to be on my team. He’s an interesting character. I love interesting characters. He’s funny. It looks like he’s doing calculations in his brain all the time.

Men's Journal: If you end up casting a vote for a million dollars, is there someone you’d like to write down?

Jonathan Young: I’d probably want to do an old school player. I would like to write Christian’s name down. I just like him. I’ve never even met him before, but I just like the guy. I’d like to write Christian’s name down, Colby, Miss Stephanie. I like the old school mindset. And if Ozzy makes it, it’d be good to write his name down.

The interview has been edited and condensed for clarity.

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