Chief Chilly

Chief Chilly is a large Big Bully made of ice and apparently the leader of all Bullies. He first appeared in Super Mario 64 DS, the Nintendo DS remake of Super Mario 64. Like the other bosses of Super Mario 64 DS, Chief Chilly takes great pride in his moustache. Bowser hired him to trap the heroes of the game along with his other minions.

Presumably at the beginning of the game he ambushed Mario, Luigi, and Wario, along with Bowser, Goomboss, and King Boo, and was put under the control of Wario or he chose to take Wario as he made fun of his moustache of which both look like each other. Then Luigi came to Wario's rescue and was forced to battle the monstrocity. Despite being the weakest of the four he managed to beat him and push him off the iceburg and the key was given to Luigi. He went home to restyle his mustache and to get a rematch someday.

In Mario Kart DS, Luigi must battle Chief Chilly in Level 6 of Mission Mode. Like the battle with Big Bully, Luigi must push Chief Chilly off his platform and into the water. However, Chief Chilly must be pushed off three times instead of one, and becomes stronger and trickier after each time he is pushed off. In fact, after the second time he falls in the water, Chief Chilly will be able to Jump over Luigi's boost attacks. To defeat him, Luigi had to attack Chief Chilly from the side, where the boss couldn't see him. Its possible that this could've been his rematch but it is not known if the Mario Kart games are in continuity or at least the mission mode.

It is possible that he is Chill Bullys father or at least was a Chill Bully at some point. That would make Chill Bully a sub species of regular bullies. He might even be Chill Bully since they both have same name, Chief is just called Chilly. Although Chill Bully appears in the game and since Chief Chilly was around before the game that theory is wronged.