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Imagine if Shaq gets drafted to the Bulls in '92. That would have been the ultimate GOAT duo in the Phil triangle. It would never be touched

There is no scenario where the Bulls would have gotten #1 pick Shaq, but in this dream yea, they win alot, probably every year they stay together, which probably would've been like his stint in Orlando, Shaq leaves, likely for Lakers, due to his ego being #2 to Jordan.

This seems like a hypothetical where the number of titles won wouldn’t really be different from what happened in reality. After all, Jordan won the titles in 1992, 1993, 1996, 1997, and 1998, and he was retired in 1994 and retired after winning in 1998. So isn’t the only potential added title the two could win together just a title in 1995 after Jordan had just come back? Unless we think playing with Shaq would have changed things such that Jordan’s retirements would’ve been different and he’d have played more years, but I’m not sure there’s a basis for that since the retirements were never really about the roster.

If we don’t assume that Jordan plays more years in this hypothetical, then I’m actually inclined to think that this has a chance of being no better or possibly worse. Not because Shaq isn’t a great player or wouldn’t fit well with Jordan, but because the potential to do better than what Jordan did in reality would require winning every single possible title. So the margin for error here for MJ/Shaq to do better than what MJ did is basically non-existent. If Shaq clashes interpersonally with the team, that could mess with team chemistry and stop them from winning the title at least one time. Or maybe needing to pay Shaq would mean the rest of the roster would not be as good as it was in reality, and Shaq gets injured or something in the playoffs and the Bulls are left worse off for a playoff run than they were in reality and aren’t able to win (after all, Shaq wasn’t all that durable in that era, and he’d be playing a whole lot of games if they were winning the title every year). I think it’s probably a coin flip whether they run the table and win every year together, or whether they win the same number of titles (or fewer) than MJ did in reality. They’d very likely win even more regular season games though.

The one thing I’d note here is that I’m interpreting this question as being how many titles MJ and Shaq would win *together*. If you put Shaq on the 1994 Bulls and assume they can otherwise keep the same roster, then I think there’s a pretty good chance they win the title that year, even without Jordan. There wasn’t any buzzsaw team that year, and Shaq was already one of the league’s top few players at that point, so they’d definitely have been a top-tier contender. I don’t think Shaq wins titles with the Bulls after 1998, though, unless Shaq being there results in the guys on that team sticking around longer.