Annotated Transcript

These Shoots are Made For Joaquin

Special thanks to Meg Birns for transcribing the meeting scene and to Suz Voy's site "The Urge" for the bar scene.

Weekly plot:
Detectives Sorenson and Sipowicz investigate the murder of a loan shark. His brother says he shot at the killer. Circumstantial evidence leads to a drunk, who is not the killer, but through him they do find the real killer, who says the brother hired him to do it. Then the brother admits he did it because he was in love with his sister-in-law.

POSSIBLE ANALOGY: The drunk represents Denby, who at first seems to be threatening Jill's job with an investigation (no matter what he says, it sounds like Jill is in trouble to start with). However, later at the bar, he gives Diane good information when he says Jill shouldn't say anything - and in fact points the finger at the prosecutor.

Denby is waiting inside for them and he singles Diane out to talk to as Jill goes upstairs with the widow.

Denby: Detective Russell?

Diane: Yeah

Denby: Detective Denby. You got a minute for me?

Diane: (not very friendly) What's it about?

She’s hostile immediately, which is strangely interesting. After all, she doesn’t know a thing about him except his name, that he’s another detective, and what he looks like. So what’s to dislike? Two possibilities: She’s gearing up for a “turf war” – he’s a detective from another precinct, come to invade her turf (?) or she feels threatened because of his attractiveness. If she’s really attracted to him, she might be hostile just to counter her own reaction if she’s not ready in her own mind to release Bobby just yet.
Interesting on his part that he specifically asks for Diane and not Jill.

Denby: (indicating Jill) Is this young lady on the job?

Diane: (confused) What?

Well, whatever she thought he was there for, she didn’t think it had anything to do with Jill. He completely blindsided her. Denby also seems to dismiss Jill with this statement by saying she has to go back to work. Well, obviously one of them has to handle the woman they brought in, but here, Denby firmly establishes that it’s Diane he’s seeking and definitely not Jill at all.

Denby: Can we talk outside?

Diane: We're not talking anywhere until I know what this is about.

She didn’t like being blindsided and she doesn’t like not knowing what’s going on.

Denby: I'm with the Narcotic Task Force. I'm investigating the information that Detective Kirkendall's husband has provided to secure his plea agreement.

(They go outside)

Well, that got her attention. And it got her to go outside.

Denby: None of this is out of school.

Diane: (sarcastically) Yeah, I like being outside when it's a little nippy.

Denby: What I'm saying is, if you want to tell your partner we talked it would be okay.

I don’t blame her for being sarcastic. He implied to her that they were going outside so as not to be overheard by anyone in the station - but now he’s saying everything’s on the record and anyone can know about it. So why bring her outside if that was so?

Diane: (irritated) See, that was my partner I just walked in with, so she's gonna know that we talked.

Denby: Yeah I know that was your partner. Her ex-husband beats jail for a full and total flip which he's nowhere close to doing yet but I'm presuming for the sake of her kids even if she thinks he's a hard-on she don't want this guy doing twenty.

Diane: So are we getting close to why I'm out here freezing?

He knew who Jill was in advance, and he knew Diane too. How much else does he know about them already? The rest of his statement says that Don is getting his sentence suspended in a plea bargain agreement because he’s agreed to testify against the cartel – but that as of yet he hasn’t given them any information worth anything. And, that he (Denby) doesn’t think Jill will want her kids’ dad to spend twenty years in jail no matter what kind of jerk he is.

Denby: (placatingly) I'm not looking to hurt her. If she's got something, she can help us to put pressure on this guy. Even if this information puts her in an awkward light, she shouldn't be afraid to give it up.

Diane: (firmly) She has nothing to do with what her ex-husband was into.

Diane is loyal to her partner.

Denby: If she needs to give it up through someone else, that would be okay too.

Diane: (more irritated) Did you hear what I just said? Jill had nothing to do with this.

Very loyal! But he’s letting her know that they’ll accept secondhand information from a reliable source if need be.

Denby: (not reacting to her anger) Her ex-husband indicates otherwise.

Diane: What?

Denby: He indicates that she had some kind of peripheral connection but he's not gonna say anything else. I want her to know I could care less about her peripheral connection. I know what women do to protect their families. My sole interest is what she can tell me about him that I can use to get her asshole ex up in the air. (pauses) You should go in and get warm. (he turns and walks away.)

In other words, Don implicated her but gave no details because he was afraid the truth might be too trivial to keep him out of jail and he wasn’t imaginative enough to invent anything more interesting that would be plausible.

end of scene

After they finish dealing with the widow of the loan shark, Jill begins to get curious about Denby.

Jill: Was it about me? Harry Denby?

Jill's knowing Harry's first name in this scene has been referenced to indicate that she was in league with Don and Harry even before Diane had ever met him. But it seems more likely that she asked 'who was that guy?' as soon as Diane got back from talking to him and Diane just quickly gave her a name so as not to take time away from their case. Jill's whole attitude being so needy for information seems to preclude that she knows what's going on with Don already as well.

Diane: It was about you.

Jill: And you haven't told me why?

Diane: And I haven't told you because I didn't know what I should do. He wants me to give you a message and I don't know if he can be trusted. He's a task force guy that's workin' with Don, checkin' out his story.

Jill: And what's the message he wants you to give me?

Diane: Jill, looking back, could you ever maybe have done something for Don, completely without knowing?

Jill: Sure I could have. I coulda dropped off boxes of pastry his mother made for private parties. Helping to tail. (finally admitting it straight out) I did.

Diane: (surprised, but trying not to show it) Oh. Whatever you gave, even if any of it implicated you, this task force guy says he'd write it up, investigate it and unfound it. So long as what you did was unintentional, he'd say it never happened.

Diane was really taken aback that Jill had done this - she'd honestly believed everything she'd said to Denby earlier. But she covers it well, maybe reasoning that she has no right to judge Jill on her weakness when Jill didn't judge her on hers.

Jill: Can we believe the task force guy?

Diane: He says he just wants Don to realize he's got no leverage.

Jill: Can we believe him?

Diane: I don't know if I believe him.

Jill: If he'd really write it, investigate it and unfound it, whatever Don starts sprayin', I'd be protected.

Diane:Yeah.

Jill: If I can trust the guy.

Diane: Yeah.

Jill: Do we give it to him?

Diane: Not yet. Let me get into him a little.

Jill wants desperately to trust Denby, but even in the state she's in can see he might not be on the level. Diane is the suspicious one, but she seems to be giving him an even chance. All in all, their reactions make it even more curious that he chose to approach Diane - if he'd talked to Jill alone, he'd have easily gotten her to tell him everything - she's not thinking. And, he'd probably know that.

Later, Diane phones Denby to set up a meeting time with him so she can 'get into him a little.'

Diane: (into phone) I told her what you said. Right now she's leaving it up to me. (pause) Well, it wouldn't hurt me getting to know you a little better. (Danny walks in) Do you have some time now? (pause) Sure. That's great. See you in a little while. (hangs up)

Danny was very interested in hearing Diane apparently set up a date. And Diane seems somewhat excited about the prospect - what reserve she does exhibit can be explained by her not knowing whether Denby's on the level about Jill.

Mary Franco, who Danny has been seeing, walks in to get some photos from a file. Danny helps her while Jill and Diane continue to talk. Diane seems very upbeat.

Jill: What'd he say?

Diane: I'm gonna meet him at Smitty's.

Jill: I mean did this task force guy say anything?

Diane: "Meet you there"?

Diane is almost rolling her eyes at Jill's anxiousness over the phone call.

Mary leaves and Danny gets nervous. Then Jill leaves. Diane goes back to work.

Danny: (to Diane) What do you got, a date of some sort?

Diane: Yeah. Sort of.

end of scene

Inside Smitty's, Diane quickly finds out that Denby has a major problem of his own.

Denby: I was on a foot post in the Bronx; two years a cop. A couple of geniuses in ski masks come out the front door of a bank - I got lucky in the shoot out. Job gives me my gold shield, make some lucky collars in narcotics...

Probably quite true. It's likely he was originally a wonder boy of whom great things were expected.

Diane: You're a lucky guy.

Denby: They upped me to this task force. So now I work regular hours - except when I'm babysitting jerks like your friend Don - I get a new car every year that I get to drive home...who's got it better than me?

The facts here are probably also true. I suspect a "task force" is on the nature of a special unit of elite officers/detectives. Interesting that one of their functions is to "babysit" witnesses in the protection program. Seems like this would be the least popular portion of their job description, meaning that it's delegated to either the newest member or the lowest on the rung ... or someone obviously on a downhill slide. The way Harry puts it, it sounds like it's not his first time babysitting.
His "who's got it better than me?" gives the impression that he knows he should be happy – that he has everything most people want materially – recognition in his career, apparently a good income (company car at least), etc. But he isn't happy or he wouldn't bother with the sentence at all.

(the drinks arrive)

Diane: Thanks.

Denby: Thank you my child. I mean now I'm safely in the lead and you're still not gonna drink with me?

Well, she did agree to meet him in the bar, so his confusion is understandable.

Diane: No.(hesitates a split second) No.

She hesitated, which means she considered it, no matter for how microscopic a time period. This is the first time she's been one-on-one in a bar with another man since Bobby died in anything remotely resembling a social outing, and even though it really isn't a date, she set it up to appear that way. So it's essentially her first time on a "date" with a guy who doesn't know about her problem when she's not allowing herself to drink. No matter that it's about to go sour - it hasn't yet.

Denby: And is this tactical? You abstain, find out what Denby knows as he yields to what is - admittedly - a small problem with alcohol? Or am I in the presence of conviction?

He's obviously suspicious, and seems to know why she's there – to squeeze him for information. He also thinks he might say too much if he's drunk and that she might have come already knowing that. But then he backs up, remembering there could be another reason she might not drink ...

Diane: You're in the presence of someone who doesn't wanna drink.

Denby: No, I sense we're drilling in bedrock here. Is it the old story - one's too many, fifty aren't enough?

He senses it because if she was there to pump him and she wasn't an alcoholic, she'd at least have one or two drinks otherwise to throw him off and she won't even take a sip of one. Alternatively, since he knew who she and Jill were to start with, he could be pre-informed about her and already know she's an alcoholic.

Diane: It's got a ring to it.

Denby: And have you now seen the light?

He's too curious for his own good. Is she for real? he wonders. He could also be deliberately testing her to see how deeply her convictions go - or how deeply she thinks they go, anyway.

Diane: This seems like a good place to take a turn in the conversation.

Denby: Gets mean behind his cocktails, this Denby. I apologize.

Denby's statement would seem to indicate that he knows the kind of person booze turns him into. Which, conversely, would indicate that when sober, he's really not like that at all (as Diane mentions later).

Diane: It's okay.

Denby: So...do you come bearing a message from Detective Kirkendall?

He is giving her the benefit of the doubt now that she must have a message from Jill, who may not have wanted to come in person. "Giving it up through someone else."

Diane: I come in peace is as far as I'm ready to go at the moment.

Denby: You come in peace, huh. Look what believing that from a stranger got the Indians. If you're prepared to have a drink with me, I could shed some valuable light on your partner's situation.

But there is no message from Jill or she'd have delivered it. And she isn't just interested in him, so ... she wants information; nothing left. VERY interesting that he doesn't trust her anymore than she trusts him. But he lets her know that he does have such information, as well as letting her know that he knows she wants it. But why make drinking with him a condition? Is he still deliberately testing her convictions, or is he just really a slimeball?

Diane: How 'bout doing that anyway, just 'cause you're a good guy?

Denby: Too intangible. We need what the devil would call 'an exchange of consideration'.

Obviously a "no, sorry, I just don't trust you" line. Unless you buy into the slimeball theory.

Diane: I'm not drinking with you.

Denby: Will you give me a small peck on the cheek?

He's already planning on the whole kiss, but he knows he'll have to break it into small steps. Why he decided having her kiss him would be good enough is debatable. It fits with the slimeball persona, but could there be another reason? Possibly he knows this should repulse her and he's still testing to see if she'd rather take a drink than so debase herself (and yeah, I think this is very far-fetched). But there's a better interpretation: From the point of view of someone else in the bar who isn't close enough to hear their conversation, if he is sitting there drinking and she sits at the table a few moments without drinking herself, then gets up and leaves, it'll appear she was just there for some information. But if she sits there drinking with him for the evening, it'll appear to be a real date. Ditto if she kisses him, even if she doesn't drink. So if someone is watching him, it's not so much Diane that he wants the "exchange of consideration" for, but this someone else. The only real problem with this theory is that if she refuses both the drink and the kiss, no matter if he informs her or not, it'll still look as if he had - although there wasn't a whole lot he could do about the situation. He had to meet her in case she had information to give him. And if he didn't know in advance that she was a committed recovering alcoholic (as opposed, perhaps, to his own experiences with trying to quit), he made a very understandable mistake with where he set up the meeting. So presumably if she'd balked at the kiss, he'd have thought up something else. This could in fact be why he asked for a peck on the cheek first - he'd be more likely to get that out of her.

Diane: (disgusted but determined) Yeah, yeah, I'll give you a small peck on the cheek.

Denby: Well this kiss would have to be a priori. You know what that means? Are you the victim of a Jesuit education too?

He's starting to get drunk – and he's a pedantic drunk. Several interpretations for the "victim of a Jesuit education" line come to mind: A) He may ask her about the parochial education to see what else they have in common besides being drunks; B) He may suspect her of being a plant to get information from him or to get him drunk, and think she's been specially instructed to have things in common with him (or appear to) - yes, far-fetched, but he is drunk, and this is just what he might think, not what is; C) The statement may be a veiled way of saying that he was abused as a child. If so, it would be almost like Milch deliberately set out to make Denby a (warped) mirror of Diane.

Diane: Come on Denby.

Denby: A priori means you go first. You peck...I shed light.

Diane: (giving him a peck on the cheek) Now, don't you feel like an asshole?

Denby: No, actually I feel rather good about the world, I feel rather set up.

The comment he makes really seems to support the "being watched" theory more than it does the "slimeball" theory, I think. If he is being watched, the peck on the cheek would, literally, make him feel set up and good about the world -- he's achieved some safe ground for claiming he's "softening Diane up" to whoever is watching, and for using this an excuse for their meeting, from which he's going to come up emptyhanded so far as information she might have given him is concerned. But if he's just a slimeball, yes, he would feel like an asshole - he'd just enjoy the feeling. And in being an asshole/slimeball, he probably wouldn't mind sharing that fact.

Diane: Your turn.

Denby: God did this, right? When there was darkness on the waters? (Starts playing with her hand) I would say this, Detective; as it applies to a Federal prosecutor, are you familiar with the legal term 'wuss'?

Not Latin this time, but a Biblical reference; he's shedding light, like God – that peck on the cheek really pumped him. More fuel for the "being watched" theory - since he seems almost happier about this than he does about the real kiss later on - which would be the opposite from what a slimeball would no doubt feel. He also adds to the date appearance himself by playing with her hand, no doubt correctly surmising that if she didn't mind giving the peck on the cheek (and she didn't put up any fight over it), she'd endure his touch to get the information.

Diane: Talking about the prosecutor that would be going to bat against my partner's ex-husband?

Denby: I'm talking about a prosecutor who's supposed to be going to bat against six Dominican and three Peruvian bad guys, against who without your partner's ex-husband's testimony, we have got evidence up the ass.

This is real information she did not previously have. It's also doubtful he's making it up – he sounds too bitter about it. So the mystery of Denby's role starts here – why is the prosecutor giving Don protection? Is Don supposed to be doing something else for the prosecutor? If so, is it something within the law or not? Does Denby know what it is? Actually, by using the term 'wuss' (and Harry is a careful user of words), he is implying that the prosecutor is weak; that someone may in fact be controlling the prosecutor and ordering protection given to Don.

Diane: So giving a deal to Don is what makes the prosecutor a wuss?

Denby: Real kiss, you get the rest. And I find myself out of scotch.

He's got Diane curious. Truthfully, she could have figured out that Jill should keep her mouth shut simply on the "peck" information alone. But he tempts her with that dangling carrot. His comment about the scotch is just his dependency on it.

Diane: (to waitress) Could he get another drink?

Denby: (to waitress, referring to Diane) And her, too.

This is probably an automatic response on his part, not something calculated, though he is probably still hoping she'll break down and drink. Just something he says as he's getting drunk.

Diane: Screw you, Denby.

Denby: Screw me? Nah, I'm a realist. My price isn't that high.

More of him being pedantic. He uses the correction to remind her of the kiss he wants.

Diane: I'm not drinking with you.

Denby: I need a wet one then.

Ditto from above. More reminder about the kiss, and that it's not just a peck.

Diane: You were a decent guy this morning.

Denby: It's not morning anymore on this part of the globe. It's good. The rest of the story is good.

He feels no obligation to be decent, he's saying. He's incredibly bitter about this, as if he feels it's even useless to try. But he does reassure her that she won't be kissing him for nothing; he's not that indecent.

Diane: All right. You first this time.

Denby: I can't rationalize that, Diane. The whole sorry history of the red man's trust is staring me in the face.

She is obviously responding to his assertion that the rest of the information is worthwhile, and agreeing to kiss him only if she thinks it is after she hears it. Since he wants the kiss regardless, he won't agree -- saying he doesn't trust her to think the information good enough, in essence. Which she probably wouldn't.

Diane: You must hate yourself in the mornings.

Denby: Only sometimes. Often I don't remember anything at all. I mean how much do you care about your partner?

This appears to be the first instance where she sees him as a fellow alcoholic, and even seems to feel pity for him. Interesting that he actually responds to her statement before returning the conversation to what he wants to talk about. His usual habit is to ignore such digressions entirely as if they'd never been spoken. This indicates that a) Harry apparently drinks to forget, b) Harry does hate himself when he doesn't forget, and that c) Harry, at least subconsciously, wants Diane to know this information. But then he breaks the "confession" mood by saying something nasty, and it works.

Diane: You prick.

Denby: (scolding with finger) Now, now. (She kisses him; it lasts for several seconds, longer than she has to allow it. He uses his tongue. As they separate, the drinks arrive, and he hesitates a moment before speaking.) I believe this is called hitting the daily double.

Fascinating here – he has two lines framing the kiss and they both have multiple meanings. "Now, now," is both a mild scold and an order ("not later"). The daily double can be the two drinks, the drinks and the kiss, the reaction(s) the kiss produced, or the two pieces of information he's giving to her. But regardless, what's most interesting about this scene is that it sets up their relationship: The kiss takes much longer than it should – he isn't holding Diane in place by brute strength, he's holding her in place by the strength of the kiss, which he shouldn't be able to do – and which he didn't expect to be able to do either (though neither is the kiss so long as to seem unbelievable). When it finally breaks, she is both embarrassed, knowing it was too long, and still affected enough (or surprised enough) by it that she can't immediately speak; she looks down, the first time she hasn't looked him squarely in the eye. He looks down too, for much the same reasons, although he finds his voice first (naturally, since he's a man of words).
There is, however, another way to interpret her reaction, based on something she says later to Jill about the kiss – she says it was nothing a gallon of Lavoris couldn't cure. Obviously, since he'd been drinking, he would have tasted like scotch, something she was trying desperately to avoid. It's possible the kiss lasted so long because she was so tempted by the booze and that Harry was nothing more than (essentially) a glass she was licking. It's also possible that this was Harry's whole motivation in asking for the kiss – he knew it was a way he could get the scotch into her mouth – and if he did, she might start drinking, especially as a glass of it was set in front of her right afterwards. If this is what was intended, it indicates an almost sexual desire for the alcohol - and this is rather supported by (as has been remarked repeatedly) the erotic way Harry fondles his glass throughout the entire scene. But Blue is so full of double meanings that I suspect the whole thing was meant as a complete picture: that there was sexual desire for the alcohol as well as sexual desire for each other; the problem with it was that at the time the two could not be separated, at least in Diane's mind, possibly in Harry's as well.

Diane: (her attitude unchanged after she spends a moment recovering as the drinks are set down) You better tell me.

Denby: The prosecutor's new boss is an anti-wuss.

He is still a bit giddy here - this quip is similar in tone to the one he made before about the daily double. Still, the notch up in his satisfaction isn't as large as the notch up he went after the simple peck - and again, if he were a simple slimeball, it would be much larger; i.e., he'd be gloating here over his triumph and he really doesn't.

Diane: I don't wanna hear any clever crap. You tell me what's going on.

Denby: The prosecutor's new boss is gonna make the prosecutor go to bat against the dealers, with or without your partner's ex-husband on the team.

He recovered a bit – now he's back in the tone he set before with the last revelation. Interesting info – Don is immaterial to the case and Denby is still babysitting him – what is apparently a useless, boring, dead-end job. This "new boss" is either not going along with or not privy to whatever it was Don was supposed to be doing for the prosecutor; which means either the "new boss" or the prosecutor is up to something illegal. Because of the previous statement Denby made, it seems the illegal operation is the prosecutor's activity. But it could equally well be the "new boss" (he doesn't say how high up this boss is, leaving it wide open – it could conceivably even be an elected official) who doesn't want Don helping with something on the side. Again, he's very bitter about it (in a sarcastic way).

Diane: Tell me what I should tell her.

Denby: You should tell your partner sit tight. Tell her...not to give me anything. (She goes to leave. He nods towards her drink) Can I have that if you don't want it? (She pushes the drink towards him and leaves) Goodnight. (The camera focuses on the glass he is holding as he raises it and sets it down still full, with Diane walking out the door in the background).

Very interesting, leaving us to wonder why he was supposed to get Jill to talk in the first place. Did someone (the prosecutor or "new boss") need a scapegoat? Was Don offering her as a sacrifice in order to try and hold onto the protection he saw possibly slipping away? This last seems most likely, but if so, it would have been for the "new boss's" benefit, not the prosecutor's. Denby's bitterness is gone with the advice for Jill, too; he seems sincere, and all in all, this does seem to be the right path for her to take. His request for the drink is genuine. He can't stare at a full glass and not drink it like she can. The hesitation so often remarked on at the end when he picks up the glass and then sets it back down is probably nothing more than him thinking about the whole thing for a moment before he continues drinking. He's just seen her going out the door; maybe he wonders if it's symbolic.

end of scene

General Observations:

Interpreting this scene opened up something brand-new that I hadn't thought of before in terms of Harry's motivation. Someone once mentioned that Harry was presented to us as if we were coming in during the last act in a three-act play about his life. I think this is virtually true. I think that Harry had to have been fairly far gone before we ever met him. In order for the prosecutor (assuming it was him and not his "new boss", just for the sake of argument, though it could have been either one) to involve Harry in his illegal dealings – essentially get Harry to do his bidding, and possibly his dirty work – he had to have known something about Harry that would have ruined his career if it became general knowledge. In other words, as the story starts, we don't know it since it's not from his point of view, but Harry is being blackmailed. The question is: what could he have done?
It can't be simple alcoholism. If Harry had made some major mistake(s) because he was drinking, his superiors would have found out about it sooner or later. So it almost has to be something he can otherwise hide. And, it's most likely something illegal (anything less and he'd probably only be in for a reprimand). He mentions some "lucky collars in narcotics" and he's still on the "narcotics task force". We know by the second set of episodes he's in that he's got a cocaine habit by then, but there's nothing set in stone to say he couldn't have had one before. We'll never know exactly what his crime was (Milch might not even have decided himself except in a general way), but somehow the prosecutor found out about it.

Possible Hypotheses:

There are several popular hypotheses about Harry's motivations going around. Since in real life I'm a scientist, I'll subject them (as far as can be done) to the scientific method and see if they hold up under testing. If anyone disagrees with my reasoning or has anything to add, please email me your logical analysis and if I think it's a valid argument, I'll include it here. The address is at the bottom of the page in the tiny letters below the police tape.

1. Harry is working undercover for either the IAB or Narcotics and is investigating Jill because of what Don said, and Diane because she's Jill's partner. He may be focusing on Diane because he knows in advance she's an alcoholic. This hypothesis gives a reason for his acting like an asshole and trying to lure Diane into drinking, if his motivation was solely to determine how deeply her convictions run. It's possible that he told her to tell Jill to be quiet just to see what would happen afterwards (especially considering what happens in the next episode). The "Harry undercover" theories come with two possibilities: Either Harry is really a drunk, or Harry is faking the whole alcoholic persona strictly for Diane's benefit. The fact that he puts the glass down full when Diane leaves (i.e. she can no longer see him continue drinking) has been used to support the "Harry is faking it" supposition. Considering Milch's writing history (see the interview with him), I find it doubtful that he'd create a "pseudo-alcoholic", but I do acknowledge he may have done so to showcase the convictions on the part of Diane's character.

2. Harry is doing exactly what he originally said he was doing for the Narcotics Task Force, although he's already planning to go into the drug business with Don. He should never have told Diane to tell Jill to keep quiet, since Jill really does need to come forth so Don can be put away, but since Harry's the one she'd be telling, he wouldn't be likely to repeat it to his higher-ups (and ruin his chance for that brass ring). Harry only said she shouldn't tell for reasons of his own (i.e. to make up something good so it sounded like Diane was well paid for her kisses, or was rambling on drunkenly, etc., etc.). This is essentially the "Harry is a total slimeball" theory. And "Total Slimeball Harry" really is an alcoholic.

3. Harry is really working for the Narcotics Task Force, who ordered him to find out if Jill was involved, and they intend to use any information they get against her. It's not the first time the system has screwed someone to let a creep like Don go so far as Harry's concerned and he's very bitter about it, so when he gets drunk, he tells Diane that Jill should keep quiet. Unfortunately, Harry's a total jerk when he's drunk (but only then). He has been teetering on the edge of just throwing it all in for awhile, though, since he really can't see much difference between good guys and bad (so what the hell).

4. As stated above, Harry is being blackmailed into something illegal concerning Don and possibly Jill. It's likely he was also supposed to find out if Jill's partner Diane would become involved in it. Possibly he's supposed to find out incriminating things about as many cops as he can so they can be blackmailed like Harry (this gives a reason for his approach to Diane and also for his ultimately telling her to tell Jill to keep quiet - he doesn't really want to find out this information).

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