I have to disagree here. He was a scumbag capable of caring and sympathy, but it didn't make him any less dangerous or slimy. He wanted his girl off of the drugs, but keep in mind that he considered her his lucky charm. He wanted her clean the same way most people don't want mud to get all over their lucky rabbit's foot. If she's always messed up, then she'll always cause trouble for him, be an embarrassment to him, and she'll likely end up dead sooner than he wants. Then he'll have lost his lucky charm and won't be able to get it back. Let's also keep in mind that if she dies young on his watch his "business associates", like Ben, won't likely be to pleased with him. There were motives, much stronger than "love" and "sympathy" involved in his insistence against the drugs, like business and pride. Honestly, who wants to have everyone know they're going with some dopey girl that can't even stand up straight and is constantly asking people if they're holding?
As for tossing people out on account of Tommy, that might have been more genuine, but perhaps not as well. His other associates obviously relied on Tommy as well, and he probably found Tommy's loyalty and effectiveness so important to his business that he could afford to throw the occasional jerk out of the club.
In any case, I'm sure that the character was aware of what people perceived in regards to his sympathy, and used it to his advantage, or at least tried to. Some people saw through it, like Jesse and Terry. Some people were just as corrupt as he and assumed it made him soft and stupid.
In any case, when he did get Jesse off the smack, she saw her folly and got out.
His plot against Terry was an example of his guile. He knew that people saw his sympathetic side and knew what a weapon that could be. He offered Terry a way out, hoping that Terry would see it as a friendly gesture and take the bait. He didn't, and that's evidence that Terry saw through Jake at every turn and simply knew what kind of guy he was.
A last example of that sympathetic personality is his offering of friendship. He was ready to be Terry's "friend for life", he said, but he was only friends with people that made him money, were of use to him, and once they stopped being useful, or let him down in any way, they were no longer friends with him.
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