Ultimately I'm trying to figure out how to piece together your hypothetical that Kobe would have ended up with at least 8 rings if he had Pippen during his prime.
So 8 years with the MDE yielded only 3 rings. Then you give him Pippen for the next 6 years after that and you claim he's going to win in 5 of those 6 years?

Doesn't add up.
Face it, Kobe has 5 rings because he already had the most help of any star player in this era by a large margin. 8 years with an MVP caliber Shaq, 3 off years, then 4 years with a front line that was probably the best in the league during that time, then he got Dwight and Nash.