Drake would have been huge 10 years ago. He's better rapper than Nelly and Ja Rule and he makes better songs than Nelly and Ja Rule.
Even when the game became
less saturated with talent as you say, Jay-Z still played second fiddle to DMX (98,99) Eminem (98-02), Ja Rule/Nelly (00-01) and 50 Cent (03-05). Then Kanye took over (04-07). Then Lil Wayne (07-10). Then Drake came in (present)

Jay-Z's skill is adapting to new eras and re-branding himself over and over again + his business decisions outside of music. Jay doesn't know what it feels like to be LeBron...because it was always nikkas better than him. Drake does though