De la Rosa's first big win came against undefeated Abel Perry by 2ndround K.O. as the headliner of a TeleFutura card. On 3 October 2008, James gave the much fearedTim Coleman the first loss of his career. In 2010, he filed for bankruptcy, which canceled out his contracts with Duva Boxing and Cavazos Boxing. De la Rosa subsequently signed a deal with Don King's promotional company.