Although I don’t think he meant it quite the way it sounded, I wasn’t crazy about Bush either. I think with Bush it was more like him trying to put Putin on the spot (to behave in a trustworthy way). ie, “you’re a nice guy, you wouldn’t do anything to harm us, would you”? Why he thought he could do that with a guy like Putin, I have no idea.
Bush said that in 2001. Putin had just been installed and hadn’t secured his power yet. Oil was cheap, had been for over a decade, so Russia didn’t have money yet. Putin was surely behaving differently at that time.