I think there's always going to be a tension between players and the front office, like like in any workplace environment where you have talent and you have people who need to manage that talent. I don't see a problem with it because generally the push-and-pull maintains a balance and equilibrium within the guardrails set by tools like the CBA (or workplace contracts/agreements, etc).
The issue is when the balance gets disrupted from one reason of another. When you have a powerful team that unjustly treats its employees, or when you have players that have enough power to dictate terms to their teams. Sometimes they do it within the legal framework of the CBA, such as LeBum where he would sign single year contracts to make sure he had leverage over his teams to sign players he wanted or pick the coach he wanted. Sometimes it's testing those boundaries, like Simmons where he either faked illness or just decided to be such a pain by not playing that the team just wanted to be rid of him.
What really drives it all is self interest and how much pressure the team feels to make a deal and if they think they have a deal that's good enough. The player may have specific places he wants to go. I don't think the team necessarily has to accommodate that. But if a player expresses an interest, and he is good enough, it can create leverage for the current team to try to put pressure on the other team to make a deal. E.g. with AD where he decided he wanted to go to the Fakers. He was under contract for a year and a half, but they made it clear that if he was traded anywhere else (e.g. Boston) it would be a rental and he would leave. Now the Fakers could have waited and just tried to create cap space to sign him outright a year and a half later, but they wanted to make AD (and LeBum) happy so they shelled out a pretty decent package for him but it still took months from the time AD said he wanted a trade. AD kept playing, like a professional, until it happened. NO is happy, the Fakers are happy, AD and LeBum are happy, it's a win all round.
Same thing with Harden. He decided he wanted out, the Nets didn't want to have a malcontent, Morey wanted to reunite with him, Nets figure that Simmons would be a good fit for KD and Cryrie, Morey manages to get rid of Simmons and gets Harden and the Nets get a decent package back. Could they have waited? Maybe, but pressure to make a deal vs Harden leaving for nothing.
Now the Simmons one is one where he didn't get to go where he wanted. He wanted a Cali team but they shipped him to Brooklyn instead. He wasn't seen as a compelling enough addition that the Cali teams were willing to sacrifice the type of player that Morey wanted in return. So he waited most of the season before he found a deal good enough. Simmons decided to call in the world's longest sickie because he just didn't want to play for Philly anymore but he paid for it financially. But it's a big hit to Simmons' reputation for professionalism, which probably affected his market.
So now with KD, there's no obligation on the Nets to trade him immediately. And they shouldn't. He's under control for four years. They can wait for the best deal. But they know it's ultimately not a good idea to force him to keep playing for them because those things never end well. They know his market will be robust, whether it's immediately or a year from now. They can sit and wait for the best deal to happen.
For me, the issue for teams with player empowerment is less to do with player movement, which is a natural part of the workplace, whether it's the NBA or your average office job. People move jobs all the time. To me it's more when players get so powerful that they start to exert an undue influence on your off-the-court operations, front office decisions. This is where player empowerment has hurt the Nets, as it has hurt the Fakers and the Cavs before them. To get KD and Cryrie Marks and Tsai basically let the players dictate terms to them: 1) they signed DAJ to a 4 year $40m deal because he was KD and Cryrie's friend; 2) allowing the players to put pressure on Kenny Atkinson to play DAJ instead of Jarrett Allen, and then firing Atkinson when it became a "it's us or him" situation; 3) trading all their depth, young players and draft picks for Harden because KD and Cryrie wanted a Big Three; and 4) allowing Cryrie to first take multiple "personal days" in 2019 when KD was sitting out and then letting him hijack their season with this vaccine demand and looking weak when they decided to let him play after first taking a stand which led Harden to leave.
It's that type of things that come with the territory when you have stars that are also prima donnas. Stars these days exert a lot of power and they can wreck your team. That's why culture and character are so important. And that's ultimately the purview of team management. They led their players hijack their team. Joe Tsai has realized that he needs to be the guy in charge, it's his team. Even if he has to lose those players. Now it's to KD's credit that of the three superstars they signed he's the only one that really showed up to work and carried them. But he doesn't want to do it anymore. If they can't find a trade partner to take him before the season starts I'm sure he will show up like the professional he is. But he will figure a way off the team eventually.