When I saw the title of this post, I thought it was referring to something I've been thinking about the past week or so. The Spurs and Celtics are in similar situations, but not roster-wise. They are similar in that they are consistently winning organizations that are not as strongly defined by their stars. They both have well-known coaches and consistent management, though Ainge is more well-known for trading his way to success than the Spurs, who value continuity and aren't constantly making deals.
The reason I started thinking about the similarity is all the free agency movement dominating the news. The Spurs thought they had the "perfect Spur" in Kawhi Leonard, who was quiet and seemingly focused on basketball only, until suddenly he wasn't. The Celtics had Irving, who bristled at Stevens' system (among other things), and Horford, who jumped ship for more money but more importantly, a better shot at winning a title.
Both organizations will not change their coach based on a superstar's request. Both organizations will not make hasty, win-now deals that are too costly in the long-term. Both organizations sell their culture of winning more so than anything their home city might offer in terms of pizazz.
Recognizing all this, in hindsight Kyrie was never going to be a fit here. He is similar to some of the other superstars out there right now that value a lot of other things other than basketball. Things like entertainment, business opportunities, market location, entrepreneurship, branding, etc. I realize I'm painting with a broad brush here, but you get the point - New York and LA, and to a lesser extent the Bay Area, are always going to provide those things which Boston cannot.
If those things are important to a player, they're not going to stay in Boston or San Antonio long term. Especially the top top superstars, they can win in a lot of places. Kawhi and Kyrie and Durant already have championships, so they're not necessarily desperate that their next team is the PERFECT situation for winning. They are confident enough that they themselves will be the source of the wins, an idea that is not necessarily wrong.
The last title teams for the Spurs and Celtics were stocked with players who don't really care about all those outside things: Pierce, Garnett, Allen, Rondo, Duncan, Ginobili, Parker. If both franchises want to get back into the title picture, they need superstars who only care about basketball and winning.