The event that would surprise me the most is:

Cheeks gives birth to quadruplets, and finds a company that will mass produce and distribute her organic candles, making her an overnight millionaire. 

Prince c lands a recording contract, and his first CD goes multi-platinum. 

Shaka collects a $15 million bounty for apprehending Peter, Maria, and Grant Montgomery. 

Rainy recieves a 6 year scholarship from Princeton University. 

Sarafina becomes a succesfful businesswoman and frequent cover on Forbes magazine. 

Nick buys a riverboat and open his own casino. 

Tuneman7 earns a law degree while in jail. Upon his release, he sucessfully beings a class action lawsuit against The Family. 

Upon his death, Bill Gates pronounces Jules as the new CEO of Microsoft. Jules wastes no time in making Johnnie Walker her Vice President.