Forever a high-roller, Diddy recently made headlines by placing $250,000 on the line in support of Floyd Mayweather, against Mark Wahlberg who matched the price in support of Manny Pacquiao. That wasn’t the first instance of Diddy repping TMT (and thank God, because you’d hate to see someone potentially lose 250k betting on a stranger). In fact, Diddy performed with Meek Mil at the afterparty of Floyd “Money” Mayweather’s 2013 victory over Canelo Alvarez. The afterparty was also attended by rappers 2 Chainz, Lil Kim, Bow Wow, Rick Ross, among others. Hopefully Mayweather isn’t upset with Diddy, who sold his mansion to his opponent Pacquiao for $12.5 million and two pairs of tickets to the big fight.