The Pokémon Sled Master was the judge at the Pokémon Sled Jump Games near Mount Lanakila on Ula'ula Island. He tended to exaggerate his accomplishments and commentary to make it seem like he was very experienced. He explained that the jumps are judged on the distance, plus the beauty of the moves. He announced that he's spent forty years concentrating on jumps and considers himself an expert at Pokémon Sled Jumping.
For each jump contestant, he kept referring to his accomplishments and after each jump, he embellished how long ago it was when he did it.
Kiawe: He said he could have gone farther forty years ago.
Jessie: He claimed he developed her brilliant jump technique of using using Shadow Ball fifty years ago.
Hala: Sixty years ago, he would have flown farther that Hala did.
Ash Ketchum: Ash apparently broke the Pokémon Sled Masters record for negative jumping distance he set seventy years previous.
Lillie: The old man apparently could have landed better eighty years ago.
Cerah: She jumps like he did ninety years ago.