Winner: T-Rex
Year: 2012

When Diddy's in the building, the stakes are guaranteed to be high. So it's no surprise that T-Rex and Ayeverb came out swinging in their first round during last year's Summer Madness 2 event. T-Rex played to the Bad Boy CEO by saying he'd go through Ayeverb's hood, take out a number of associates, and claim a body 10 years down the line, like G.Dep. Ayeverb returned the favor, taking down Rex's hometown of Harlem piece by piece, finishing with: "Harlem can't control A$AP; he made Texas music and sip sizzy/Harlem can't control they hoes, Jim Jones can't even control Chrissy." The cameras cut to Diddy wildin' in VIP over that.

Right after that, the stakes literally went up, as Diddy sent down $10,000 to go to the winner of the second round. And how does Rex respond? "Mook wanted 25k to kill a n***a that's ill/For this 10k Diddy got, I'll kill this n***a for real!"