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.
After about a month into the competition, the Oceanbacks and Sunbrights were tasked with their final pre-merge challenge. 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 3/4th tokens. Chalkboard knew the only way to prevent this fate was to quit, thus cancelling the elimination and letting his 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 is the first merge boot.