Did Deep Blue beat Kasparov? That’s a way harder trick than picking between Kevin Knox and Shai Gilgeous-Alexander.

You can’t measure heart yes but heart’s not a thing really.

Does someone who has spent years studying and analyzing the game of chess BUT NEVER ACTUALLY PLAYING IT know as much about chess as a real grandmaster?

GMs study and analyze the game of chess, too. That’s in part how they become grandmasters.

The bigger problem with your analogy is that chess is a game wherein there is no environment-based luck. There are objectively good moves and there are objectively bad moves, and they are rather easily quantified to near-perfection by chess engines, and improved upon by the finest AI known to the public. There are discrete turns wherein an opponent is fully unimpeded from making any legal move. When one player makes a mistake, his opponent has full authority to punish the error. There are no interaction effects in chess. There is no physical fatigue beyond the mental; a gravely-ill, deliriously-sleepy, quadriplegic chess player is fully capable of playing the best possible move, should it present itself. Not a good comparison at all.

Maybe 3 first rounders… per year… for the duration of his contract.

Does someone who has spent years studying and analyzing the game of chess BUT NEVER ACTUALLY PLAYING IT know as much about chess as a real grandmaster?

This is a sloppy comparison, IMO. In organizational sports there is a division of labor and knowledge within franchises that you don’t see in individual sport/game competitions like chess. Yes, it is true that a Morey or a Hinkie do not have anywhere near the same intimate level of knowledge regarding on the court basketball play as an NBA veteran like Jalen Rose does. But they are executive level personnel, not basketball labor, so “playing the game” at an NBA level isn’t necessary requisite for them to manage their organizations. If this were so, Magic Johnson and Michael Jordan would be the two greatest executives of all time. And then there is the Jerry West type exception, but fuck it, he’s white, played at a HOF level, and was a great basketball executive before analytics took hold.

If it were up to me the entire NBA organizational structure would be restructured top-down so that the league would “de-corporatized.” I would create a situation where the players own half of the league, union veterans have major managerial say, there would be no private ownership of franchises, and they would be managed under a public trust that kicks back to the municipal communities who subsidize their arenas.

Way more than they’d ever give.