Darry-He at first was the richest but somehow lost like most of his money.
Johnny- He bought tons of property and became the second richest
Twobit- Honestly didn't know how to play the game so he just kept losing all of his money from Johnny.
Ponyboy- Multitasking as he plays he also handles the money.
Steve- Acts like a game host.
Soda- Somehow Sodas winning for a particular reason and no one knows why.
Dallas- keeps getting go to jail card and finds it an insult and just knocks the whole board off the table making a huge mess.