Gentry is like Wade Phillips. Great Assistant Coach, Bad Head CoachIn my opinion, he was a three time loser when we hired him. You don't give a guy that failed the driver's test 3 times, the keys to a Ferrari (AD). I like the man personally. I think he's genuinely a nice guy. He just isn't an NBA head coach. Sorry, it is what it is.
One way to judge a coach is to see how he takes the talent he is given, and then see what he does to get the most out of that talent. Gentry runs his system. If the players don't fit the system, he is ineffective. Unlike other coaches who adapt to their talent, he has a preconceived notion as to what they should be able to do as opposed to what they are actually capable of doing.
Contrast this to Brad Stevens. Give Stevens 15 decent guys, regardless of whether they fit his system, and 8 times out of 10 he will get at least a 500 record out of them, and 2 or 3 times, he probably gets at least the 8 seed and makes the playoffs. Stevens will adapt to the talent. I would argue the same for Doc Rivers. Gentry just isn't that guy.
He also isn't a Phil Jackson or Greg Popovich type that can make a player believe in what he's running so the player adapts. Heck, he couldn't even talk AD into playing center even though it was his arguably his best position. I was by no means a Monty fan, but to my eyes, he is a clear downgrade. At least you got the sense that players wanted to play for Monty. Not the case with Gentry, take Jrue for example, he stayed because of money and the fact that he wanted to play with AD. Not the same.