- If Wizpig brainwashed the bosses of the island, why do they congratulate the player for beating them, then giving them a piece of the Wizpig amulet for beating them a second time?
- Well in the manual it states that the first time they're beaten the spell is broken on them for just long enough to activate the silver coin challenge, so it's because they're temporarily freed from Wizpig's spell and completely the second time which is why they give you the amulet pieces, if you want to ask why they still race you after beating them a second time, you may as well ask why Wizpig's head is still carved into the mountain after beating the game rather than Taj as we see in the ending and it's pretty clear Future Fun Land's trophy race happens after Wizpig's defeat.
- Maybe they were never brainwashed to begin with but only pretended to be, and want to make sure you're up to the task of taking on Wizpig in a race, which is why they're supportive of you regardless of the outcome. They WANT you to win, but they're not going to just hand victory to you, they want you to be better than them. Remember, they're the island guardians. They throw everything they have at you in the races against them because they know beating Wizpig will require you to be good enough to beat them at their best.
- I remember the manual explaining that the bosses didn't want to race against Diddy and friends, but were being forced by Wizpig somehow. I also recall reading in the manual that the dinosaur boss had family members who Wizpig was keeping hostage. Maybe when Diddy and pals said they'd take out Wizpig, the bosses actively joined the good guys.
Headscratchers / Diddy Kong Racing