The arguable winner of the Tupac Shakur and Notorious B.I.G. feud was Jay-Z. He entered the game when the feud was at its peak. His association with Tupac Shakur made him among the many targets. It has been said that on Tupac's "Hit 'Em Up" that the muted part of the outro was some choice words for Jay-Z. While that diss was left out, there were many shots that Tupac sent at Jay-Z. Before he could respond, though, Tupac was dead.
In the time since Tupac died, Jay-Z avoided a feud with one of the best rappers of all-time. On his next album, Hov would shout out Tupac and his friend, The Notorious B.I.G. Following his sophomore album, Jay-Z would catapult into superstardom. Each of his following albums would go platinum and Jay-Z would soon become the biggest rap star on the planet. He expanded his brand through his clothing line, his record label, and his retirement, which led to him becoming the CEO of Def Jam.
But, had Tupac Shakur never died and the planned diss record from Jay-Z had been released, things could have been entirely different. The way that Tupac was feeling in 1996, he would have sent his entire squad after the entire Roc-A-Fella crew. Not too many people realize that Bad Boy was on its last leg because of the feud with Tupac. Because he died and Biggie expressed his condolences and then released "Hypnotize," the people continued to listen to their music. But, with Jay-Z being the right hand man of B.I.G. and ready to take Tupac on, their feud may have continued. What is likely, however, is that Tupac and Biggie would have met in a public place and their feud would have died.
Just like how Jay-Z and Nas ended their feud, they went on to make appearances on each other's albums and on albums with other artists. With Tupac never really wanting to feud with Biggie the way that he did and with Biggie wanting peace, their feud did not have legs. They would have probably ended things by 1997 and Jay-Z may have been invited to work with them. With Tupac and Biggie still alive, they are still on top of the rap game. Throughout the career of Jay-Z, he has been noted for "sampling" lyrics of Biggie and he has even used some of the rhymes of Tupac. But, with them still alive, that is nothing more than biting, so Jay would have been more original. His style, compared to their styles, would have never caught on. Right now, instead of being considered one of the top rappers in history, he would be on the popularity level of Keith Murray.
While his feud with Nas may have still happened, neither rapper would have been as high-profile and with no attention, the feud would have died shortly thereafter.