Insanul: Hard to say, but I’m gonna go with Jay. For one, he’s dealt with a lot more rap beef than Kanye has over the years, so he’s more equipped to handle it. Kanye tends to let his emotions get the best of him, while Jay is just cool in the cut, which might help him from doing something too outlandish that would hurt him more than it helps him.
Either way, Jay has a lot more to gain from this than Kanye does. In the past few years, Jay’s status as the GOAT rapper has taken a backseat to Kanye’s status as the greatest artist rap has ever seen, with his influence going far beyond just rap itself. Some of that has lead to people questioning Jay’s relevance and, amazingly, his cool. Anyone who follows culture closely currently holds Kanye in higher regard than Jay, even through casual observers are likely to side with Jay over Kanye just because Kanye has pissed so many people off over the years with his antics. If Jay could find a way to come out on top, he’d briefly have the upper hand on Kanye, something he hasn’t had for quite a while.
Justin: Kanye is the least reasonable entertainment figure since Mike Tyson. Kanye West isn’t even an entertainer so much as he’s a total spectacle unto himself. He has a blast radius. That blast radius being significantly wider than the dimensions of a Midtown elevator.
I just don’t think Jay can really “win” anything, anyhow, in any sort of spat with Kanye West. Again, Jay could stifle Kanye to a draw. He could diffuse the situation in some typically clever, graceful way to remind us that Hov, post Roc-A-Fella, is a class act. But there’s no scalp for Jay Z to collect here. Kanye’s the little brother with everything to prove. And little brothers can be tenacious as fuck.