After the first team challenge of the season, Era 3 captains Tony and Averey walked away in the position of power. They should have been able to shake up the game and keep themselves safe, but somehow, they messed it up so royally that they ended up in the Arena.
Tony wanted to keep Kyland and Kaycee safe to build an alliance down the road. Averey wanted to keep Derek and Aviv safe because she has a longstanding friendship with Derek. Neither team captain was willing to budge, but most people understood Averey’s perspective. She doesn’t have a lot of relationships in the game, and she’s known Derek for many years. He’s a true ally, and people expect her to want to protect him.

Meanwhile, Tony had just met Kaycee and Kyland a week before his victory, and they were practically strangers in the Chamber. The Era 4 players hadn’t offered to work with Tony until they needed to persuade him. Their offer for future safety was a hypothetical situation that was fairly unlikely to ever happen, but they needed to benefit from the alliance immediately.
However, it is true that Kaycee and Kyland are more likely to find themselves in positions of power than Derek and Aviv. Not only are they physically stronger players, but you could argue that the Era 4 team is more likely to win in the future than Era 2.
We can’t dismiss the fact that Tony could have earned favor with Darrell by giving him the opponents that he wanted, but if he felt Era 2 was unlikely to be in a position of power in the future, Era 1’s chances are far slimmer.
However, Tony also entered the Chamber stating that he didn’t trust anyone, and Kaycee and Kyland’s offer seemed paper thin. On the other hand, Aviv has few allies in the game (so she’s unlikely to betray the ones she makes), and Derek has a long history of defending his friends. If Tony was going to trust anyone, the better option is fairly clear.
We also saw Bananas try to convince Tony to compromise with Averey, but Tony stood his ground. In Tony’s defense, he probably was upset hearing Bananas cheer for Leroy during the Eras Invitational and he recognizes that Bananas has selfish intentions by trying to keep Derek and Aviv on the Era 2 team. Despite this, the conversation should also be a sign that Tony does have allies in the game. Even if Bananas would have prioritized Leroy, that was a thing of the past and Tony is almost guaranteed more safety with Bananas than Kyland or Kaycee would have offered.

After looking at all of the points, it really does not make sense for Tony to try to keep Kyland and Kaycee safe in spite of Averey. Most likely, Tony was just in a really bad position on his team and was willing to go home.
We also have to consider the fact that Tony let Zach and Amanda go into elimination on Final Reckoning to keep himself safe. On that season, Tony wouldn’t even step up for the sake of his best friend Zach. This time around, he was willing to jeopardize his game for hypothetical allies Kyland and Kaycee. And objectively, Averey was right: Sending Kyland and Kaycee into elimination is more likely to send a strong player home than sending in Derek and Aviv.
It looks like Tony’s heart wasn’t in the game this time around, and it’s a very disappointing showing. A lot of fans had been waiting for Tony’s real return. We all respected his decision to depart from All Stars 4 to address a personal matter, though Averey claims no one (including Nicole) knows why he left that season in an interview with Entertainment Weekly. This raises suspicions about both of Tony’s recent departures.
While Averey believes Tony was willing to leave Season 40, she also noted that he never packed his bags before his elimination, indicating that he may have been relying on her to back down and vote for Derek and Aviv. While this could be the case, Tony also knew that he wouldn’t just leave the show without collecting his belongings (based on similar instances, like Zach and Amanda on Final Reckoning). So, it really feels like he wasn’t invested in Battle of the Eras and just wanted to get his appearance fee and get out.
