What has happened historically has to be taken into account. But even within that historical context, each situation is different.
Had the org been willing to extend some players...Brantley, Santana, and VMart come to mind...they probably would have stayed.
But Brantley had severe health questions at age 32. Santana was 34, coming off an awful season, and Covid hit. Victor would have been 32 when he hit free agency, and the team was in full rebuild.
Joses situation is far different. He will be 30 when his options run out, is among the truly elite players in the game, and the team is not rebuilding.
Also, as has been mentioned, he has chosen an agent who prefers extensions to free agency. Not only did Jose choose him, he chose to stay with him when he began his own agency. On the surface, Jose does not look like somebody looking to move on from Cleveland.
While you can't ignore the history of Cleveland and its better players, you also can't ignore the decisions that Jose has made leading up to this point in time.
You also can't ignore the fact that Jose may be the most anonymous superstar in the game. Unlike Lindor, the anonymity that playing in Cleveland provides seems to fit Jose just fine.