playing with them for those 8 years.

Nowadays people like to think of the Bulls as Jordan and Pippen but Horace Grant was also a key member of that first 3-peat squad and almost just as important as Pippen for his tough low-post D(he was 4x All-Defense) and as the #3 scorer he was really considered to be part of the Bulls "big 3". After the 93-94 season he signed with Orlando as a free-agent and they missed having him down-low big time in 94-95 and that forced them to trade for Rodman which was seen as somewhat of a desperation move at the time but it worked out and Rodman was a major part of that 2nd three-peat.

So that plus taking into consideration the possibility of injuries and other issues dealing with contracts and egos and whatnot it's hard to say realistically.

With a "dynasty" type team like that in a modern media environment it's like a 24-hour circus around the team and that wears on guys after a while. The stars can usually handle it but not the role players and that's where things usually start to come apart. Outside of Jordan and Pippen the 2nd 3-peat team was completely different from the first and those seasons in between were sort of "reboot" years, it would've been tough to do that only the fly while still winning titles every year.