The rolling the ball thing reminds me of another thing that has always bothered me in NBA basketball. When there's 20 seconds left in a game or quarter even, why does the defense let the offense dribble the ball at the top of the key with no pressure and allow them to dictate when they make their move for the final shot? If I were the coach, I'd have them pressure them the whole time so they can't get comfortable before making their final play for the last shot.
I think that has more to do with fear of fouling. You don't double in that situation because someone will be left open, we see that happen to the Suns quite a bit. They'll double the ball handler and give up a great look by a wide open teammate, the Wizards vs Suns game comes to mind when Booker was guarding Beal and Bender doubled which allowed Thomas Bryant to get open. I don't think you want the player to pass though.
If you pressure the ball handler too much then there is a chance they can slip past their defender. By being a few feet away you can have your arms extended and take away more space. If the ball handler puts the ball on the floor and tries to make a move it only takes a small shift to get in front of them, the ball handler basically walks right into coverage. The defender doesn't know which way they'll go so they need to guard both and having a few feet between them allows for them to lean into either side to try and stop them. You want the ball handler to take a shot themselves, if anyone does, and the further from the basket they are the lower their percentage generally is. So as they closer you close the gap more and more but that also has to do with having less room behind you, as the defender, and having help on the sides because your teammates are there.
I think that's really the only way you can guard it. I may be misunderstanding what you're describing, I'm not sure. I looked at the Lillard 3 over George because I think that applies to what you're saying. If the ball handler shoots form that far out then you're grateful you didn't get them a closer look. It's not often players drain 40 footers like that. I know there was debate about that shot in particular, it wasn't a great look for Lillard. Some say it was but I still take PG-13's side in that he didn't give him space to get a better or closer look and a player taking a 40 footer is a bad shot, regardless of his percentage from out there. His percentage from out there isn't as good as it is right on the 3pt line.
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