A contestant who didn't take himself too seriously, Chalkboard played an interesting game which ultimately ended at the first elimination of the merge. Chalkboard was a strong challenge player, and was definitely the best of the Red Raiders. Because of this, he was never targeted. In the first elimination, he decided to vote out Peanut over Green Ornament, because he saw him as a strategic threat. However, this negatively affected his team, and they lost again after the swap. Chalkboard and TV Dinner voted Green Ornament, while Shield Juice voted alongside Green Ornament to vote TV Dinner. Ultimately, Shield Juice switched to Green Ornament and they went home.
When the teams switched up, Chalkboard immediately lost the next challenge, which was not the result he wanted from the swap. Because of this, he and the rest of his team decided to keep the team strong and eliminated Shield Juice. This was the right decision, as Chalkboard was not put up for elimination until the second team swap, where Shades was unanimously voted out. When the merge hit, Chalkboard was in the worst position out of anyone, since he had no original team members left in the game. He tried to gather as many people to eliminate Chips as he could, however this proved to be too difficult and he was voted out.
Chalkboard almost rejoined, however he was narrowly beaten out by Bouldery's entry.
Chalkboard tried to keep her threat status low-key during the beginning of the game as she was a returner. The only notable thing she did before the team swap was create an alliance titled the "Winners Alliance". This alliance consisted of herself, Slush, Pineapple Pizza, Apple Bite, Dart, Chandelier, and Snack Basket.
Once the teams swapped, Chalkboard was placed on the Oceanbacks again. The Winners Alliance thought they had the majority on this team, however one of their members, Apple Bite, decided to flip to the other alliance, and Slush was eliminated. After this, Chalkboard found herself in the minority, and tried to win as many challenges as possible. Luckily for the alliance, there was a rejoin where Slush and Brushy came back into the game, where both of them decided to ally with Chalkboard.
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After the Oceanbacks lost, Chalkboard proved his nobility to his alliance by quitting. Chalkboard knew that if the elimination were to happen, the only way to outlast the rivaling alliance was to waste one of Pineapple Pizza's 3/4 Tokens. Chalkboard knew the only way to prevent this fate was to quit, thus cancelling the elimination and letting the rest of the alliance live another day.
- Being drawn-on, Chalkboard is currently the only contestant with a unique face design.
- Chalkboard is the only original Red Raiders member to make the merge.
- This also means that Chalkboard has the highest placement out of any Red Raider.
- Chalkboard was the first merge boot.
- Chalkboard is the first returning player to quit the game, and the second person to quit overall, following Lyre.
- Even though Chalkboard placed fourteenth, he had the best challenge average of the season (excluding Crowbar, who debuted.)