Industry Insider Reveals "Secret War" Between LL Cool J and Jay-Z
“[Dame and Clark] figured if Jay was known as the dude that kilt LL in battle, record labels would take note and give him that much sought after deal,” wrote Ossé. “Dame and Clark had the plan laid out, whenever LL was spotted by either of them, they would page each other and Jay and get him to meet at whatever location LL was. This went on a couple of times. Once contacted, Jay would roll up to the club, bar or whatever venue and lay in the cut, waiting for his opportunity to attack LL in battle. Dame would polly with, then taunt LL about how Jay was nicer than him, was ready to take his spot even. LL's ego would result in him agreeing to go head to head against the young and then unknown challenger.”
At the time (circa 1992) LL had found success with his Grammy-winning album Mama Said Knock You Out, and was known as the king of battle Rap. However, as Ossé tells it, LL had lost those secret battles with Jay-Z.
“Dame and Clark would end up in my office the following day, laughing about how Jay lit that ass up. Every time too. They was a bit sour too, cause after each battle, LL would kill the vibe, crush Jay's high by flinging the ‘Yo, my next record is dropping next month, uhm, when's yours coming out again, scrap?’ line at him. Jay, Dame and Clark didn't like that shit. Not one bit. I'm betting those battles are the reason LL is still kinda aggie towards Jay.”
Between 2006 and 2008, Jay-Z's presidency at Def Jam Records resulted in a public disapproval from veteran artist LL Cool J, who felt that his career and projects were mishandled, despite deing an artist since 1985 for the label.