Having first competed in Brains V Brawn, Simon had a lot of unfinished business with the world of Australian Survivor. Blindsided the day before merge, Simon became the first in Australian Survivor history to be voted out while possessing two hidden immunity idols. This time around, the chippy returned to prove he had what it takes to go all the way.
But the Survivor gods had other plans, and Simon's game was marred with blunders, blow-ups and an "idol" that changed the direction of his entire game.
With George flanked by multiple alliances, the vote came down to a tie between Simon and Nina, and upon a re-vote, Simon's time in the game came to a quiet end.
"I am just exhausted," Simon told 10 Play, laughing, "it has just been everything I could have ever imagined and more. To be part of one of the most amazing seasons like this, but it was a lot."
Coming back into the game Simon's main goal, aside from winning, was to make it through to merge. "I just wanted to make it far enough in the game to get that merge buff, and then the chance to be there at the final tribal council -- whether I was sitting and pitching to the jury or deciding the vote.
"I just really needed to fulfil that dream as a fanboy, and I'm so grateful I got that chance," he added.
Landing in the Villains tribe, almost immediately Simon set his sights on getting George out of the game. "He loves the game as much as I do and has the potential to be one of the greatest players ever," Simon explained. "I think I saw that as soon as he stepped on the beach, how big of a presence he was."
He knew he had a choice to make, either get behind George and work with him or carve his own way through the game, gunning for the title of Kingslayer. "I very quickly said you know what? This big threat needs to go. Once I made that decision I had to live with the consequences of my actions and it really dictated a lot of my game."
Simon's attempts to get George out were first unravelled by the other returning players who saw George as the perfect shield to go deep in the game hiding behind. Post swap and merge, George had surrounded himself with allies who refused to make a move against him, to many of their own detriments.
"He's such an amazing operator, so to warn everyone about it and see it happen in front of my eyes was extremely frustrating. So many people fell under the rule of King George... I did everything I could to warn everyone," Simon added.
His rivalry with George came to an incredible head during the now-infamous tribal council that saw Simon win his first individual immunity, unaware that the tribe were planning to blindside him. Everything had aligned perfectly for George to be voted out, and then Simon's game exploded in front of him. George managed to out Jordie as a double agent, convince Stevie that Simon wasn't ready to make big sacrifices for him, and blindside Fraser all at once.
"To win myself the individual immunity necklace, and to do it when I needed it the most was so cool. And then that whole thing is overshadowed by the chaos to come," Simon said.
"At the time I felt like I was having a bit of an out-of-body experience. Is this actually happening? It was really tough to see it all happen then, to re-live it definitely brought back some really raw memories," Simon admitted, adding, "But geez it was entertaining. It was incredible to be a part of."
At the same time, Simon was holding onto what the thought was a hidden immunity idol. It would be days later that the truth would finally be revealed to be a hint for the location of an idol, but Simon's whole game was shaped around what lovingly became known as the Cookie Idol.
"It was the defining point of my game, it gave me the confidence to poke the bear and have a shot at the King in the first place," Simon explained. "It was the reason I burned trust with every single person in the entire game. That thing defined my whole season in the game of Survivor."
Admittedly, Simon said he had his suspicions when he found the token without any paperwork that usually accompanies idols. "I found this official-looking disc in a reward that feels like it should be something... it just kind of ate away at me," he said.
"I didn't have much time between finding it and potentially having the opportunity to blindside George that I had to jump on it and see if it worked. I had made that assumption there, it ran away from me and I had to deal with the consequences."
Playing under the assumption that he had an idol, to the point where he was attempting to do cross-tribe deals to prove his loyalty, Simon's game was defined, and changed, simply because he believed what he was holding was an idol.
"It's actually terrifying watching it back and seeing the little X through the idol like, wow I would have made so many different decisions if I didn't have that, and the repercussions of it all.
"It literally set my game up for failure from there, and it was kind of heartbreaking to see," he said. "At the same time, that was the narrative of my storyline. I managed to push through and it aided me to get so far. It put me in a position I didn't expect to be in and that set me up for the endgame."
That position is what Simon would later call "severe bottomness", having made it to merge with no visible allies and only his ability to win individual immunity on his side.
Had he come into merge as a challenge threat surrounded by allies, Simon is aware he would have been one of the first to be booted from the game. "It put me in the complete opposite position to what I expected... and that set me up for the endgame to get myself to merge, get on a bit of an immunity run and actually have no threat and a place at the bottom. It really helped me progress through the game.
"In a way, it helped me manage my own threat level and I pushed myself to the bottom of the tribe to reduce my threat level so much it was like, 'We can get Simon later, he's got no power, there's nothing he can do'."
His lack of agency in the game was so great that he was the last remaining player to not receive a vote against him, lasting 37 days before his name was written down.
"You have to have a lot of resilience to be able to be alone and have no one there for you and keep showing up for yourself," he said. "It really pushed me to my limit but I did it and I'm so proud of what I achieved."
In the final days of his game, Simon desperately tried to wake the remaining players out of their diehard allegiance to George. Ruffling a few feathers, Simon called out Gerry, Liz and Matt for being 'pawns' to the king.
"I meant it only in the sense of the game," he clarified while standing by the comments he made on the beach.
"Never being in their alliance, I never got to see the inner workings of it, but seeing the way George was manipulating the newbie players is just so obvious," he explained. "I knew that he had been in their ear, talking up their game, that Gerry was one of the best strategic players to ever play. When you've got someone in your ear telling you that, you start to believe it.
"The analogy I used was I had been knocking on the door for a long time, I tried bashing on the door, and then I had to fully rattle the cake. I had nothing to lose."
"If I could just get them away from him a little bit and see how warped the reality of the situation was, it might just be enough to change. I almost got through to Matty and that's the frustrating thing about it. He at least understood how it was seen but, unfortunately, didn't think it was the right decision to move forward. We'll find out if that was a $500,000 decision or not."
With his torch finally snuffed, Simon joined the rest of the jury and was shocked to learn that they were all Team Simon.
"Everyone was like, 'We were all so excited for you, you never gave up, you were standing up to this dictatorship and you were the only one doing it'. I was a little bit at the time just like, yeah I'm sure they say this to everyone," he laughed.
"After a few conversations it was really humbling to be like wow, it was really nice to have that support and see my game respected when I had nothing, but I didn't give up and I was still trying to make moves and still trying to keep my torch alight pushing for one more day in the game."
After Hayley's blindside, Simon said he finally started to believe if he could make it to the end of the game he'd have one of the most compelling narratives for the title of Sole Survivor.
"I knew I'd have to pitch my little arse off and pull the biggest final tribal pitch since Kristie in Season 1, but I started to believe I could actually do it. I thought I was one of the only remaining players that could beat George."
The members of the jury weren't the only ones who were won over by Simon's charming series of unfortunate events that saw him fumble through the game. Earlier in the season Simon was routinely the target of negative comments on social media from viewers but in recent weeks, a surge of support has become to outweigh the naysayers.
"I've definitely felt that change," he said, "it was really tough at the start to watch that and, to be honest, even watching myself back I felt like so much of my human side wasn't shown in the early days.
"When I was on the bottom, that all became part of my story. The real Simon really came through where I'm passionate about what I do, so grateful for the opportunity that I had and the support I received," he continued.
"People love an underdog and it was so overwhelming. A nice change from the start of the game through to now. People were behind me and had my back and were appreciative of the game I played."
Similarly, despite the barbs traded and the tribals that seemed to get very personal, Simon forced himself to leave that all behind, immediately after the votes were read he thanked George for "everything" and admitted what a pleasure it had been going toe-to-toe.
"It is really tough, and it can be difficult to separate the game from real life but at the end of the day, it is a game," Simon told 10 Play.
"I love this game so much, I care about it so much and I've put so much of myself into it and it's given me so much back in return," he said. "If I wasn't able to make peace with my game and with the players, it would eat me up inside... some things are more important in life."
"I'm so glad I got so much out of this experience and [to be] part of something so special to me."
As for if he'd return to the game for a third shot at the title of Sole Survivor, Simon laughed. "I need a little break, to be honest. I am broken but, when the time is right, we will see.
"It's definitely not a no, I just need some time to recover, to repair and to focus on some other really exciting things happening in my life. Right now I just need a break."
Australian Survivor: Heroes V Villains airs Sunday - Monday at 7.30 on Network 10 and 10 Play on demand