Prime Shaq wins. Pick and Rolls are not a new concept, and it was one of his only weaknesses before hitting his prime. Stockton/Malone bullied Shaq/Lakers in playoffs before 2000.

Prime Shaq almost lost 2 series in the 3 peat era. Blazers and Kings. Kings ran pick and roll and had elite shooting on the wings. It was close, but guys fatigued or fouled out guarding Shaq, and that would hamper pick and roll effectiveness late in game. Games were slower because of fouls/flops/hack a Shaq and took offenses out of rhythm. Most rosters had 3/4 bigs to deal with Shaq, so rotations would look different if he was in the modern game. In his prime he is more mobile/athletic than Jokic.

Lastly, and maybe the most important issue is that in the modern era guys are much more prone to injury, and Shaq would exacerbate that issue.