This old guy claims to be a master at golfing, and every time he tells an outlandish claim, it happened a longer and longer amount of years ago. He resembles the Master Fisherman and Sled Jump Master, it's unclear if it's the same person.
He would keep exaggerating his experience:
40 years - Master Pokémon Golf caddie, which makes him a legend.
50 years - Caddie for 50 years and only foolish would go through the course without him.
60 years - Apparently the first golfer to come up with the idea of using Tailwind on that golf course.
70 years - Master Caddie that had seen all kinds of miracles many times.
80 years - Master Caddie that insists that relaxing through deep breathing should be done daily.
90 years - Master Caddie that can show easier putt lines.
99 years 3 months - Showcase the extent of his true power on the Tenth Hole of Doom.
99 years 6 months - Master Caddie acknowledges that one mistake can ruin everything.
99 years 9 months - Master Caddie realizes there is nothing for him to teach at the secluded hole.