Given that, it should come as no surprise that Bryant, now 41, desperately wanted to match Jordan’s biggest NBA accomplishment. By the time Bryant’s career was over, he wanted to win six NBA championships. Bryant never got there. And while Bryant won five rings and cemented his legacy as one of the greatest players of all time, not winning a sixth ring really “pissed” Bryant off. Bryant revealed that on the “All the Smoke” podcast with Stephen Jackson and Matt Barnes. The Jordan conversation begins around the 27:50 mark.