I don't really have any internal conflict: a team should always be striving to win a championship. For a team with the resources of the Celtics, one championship in 33 years, and only being a legit contender in two of those years ('08, '10) isn't really acceptable.
I want to win. There are no more "good guys" to root for. You know what's going to happen if Jayson Tatum becomes a top-5 player, as unlikely as that is? He'll turn into a diva, too. You can already see the beginnings of it. So, if it's "winning with jerks" or never winning, I guess I'll have to deal with the jerks.
And, the idea of our team being "fun" doesn't seem all that likely to me, either. Tatum isn't a fun player for me to watch. Too little defense, too many long jumpers, too little passing and making smart plays. The same goes for just about every single player not named Brown, and sometimes Hayward and Smart.
I'm pretty much with you on this, Roy. Since the glory days of the original Big 3 during my childhood, the Celtics haven't had many outstanding seasons.
And like you say, waiting for "our guys" to develop—if they even do end up developing into great players (far from guaranteed)—carries the risk of having them become prima donnas who want out, just as they're coming into their prime, like what AD just did to New Orleans.
And like you, I'm already kinda tired of Tatum's act—throwing up his arms after almost every one of his missed shots, and his insistence on keeping the least efficient shot in basketball as the cornerstone of his game.
Yes, we're likely to hang on to Tatum and Brown longer than we would've been able to hang on to Davis, but in the end, I don't think Tatum/Brown is more likely to lead Boston to a title than Irving/Davis. Furthermore, the much-ballyhooed Eastern Conference Finals run of 2018 came about in part because those guys (especially Tatum and Brown) had no pressure on them—with Hayward and Irving out, no one expected the Celtics to do anything, so the young guys could play free and easy. Now, however, everyone in the world, including those two, knows that Danny picked them over AD, picked them as the main pieces of the next phase of Celtics history, and that's a lot of pressure.
I don't know. I want to cheer for whoever's wearing Green, and give them my full support. But the cynic in me says that Tatum and Brown better be the next Pippen and Drexler, because that's essentially what many Celtics fans are saying they'll be—all-NBA types who are gonna lead Boston to multiple titles in the coming years. But honestly, I'll be surprised if the Celtics are even in the NBA Finals in the next 3 years.