Things going for Jay:
He's gone platinum more consistently than any other rapper
No rapper's ever been able to bridge the gap between street and mainstream as easily as he can
Things against him:
Skill-wise he really isn't the best at anything, Rakim, Nas, Biggie can do everything better than he can.
Mainstream-wise, yeah, he probably is the GOAT, but in terms of an actual body of work, no dice