Why doesn't Fagin just report to the police that there's a madman threatening him for money?
Well, because he would probably have to confess that he made deals with a loan shark, which is not exactly legal. That and the fact that Fagin is a thief (albeit a harmless one) must have been what kept him from seeking the police. It´s also possible that Sykes could have killed the policeman sent after him and for Fagin, it would only make things worse if Sykes found out he was the one who tried to get him arrested.
Sykes is heavily implied to be high up in the Mafia. That's not the kind of person you snitch on without repercussions.
But Fagin could have anonymously reported Sykes to the cops/FBI
Who says he DIDN'T try that? The authorities probably wouldn't take the word that seriously unless they knew details that Fagin would be reluctant to mention.
Fagin also doesn't know how much influence Sykes wields or what connections he has, meaning he wouldn't know whether reporting Sykes would fix all of his problems or make them worse. Additionally, he has to understand that as a homeless bum, he has no insurance that someone won't come after him eventually if he's even speculated to be a liability — it's not as if anyone is going to miss him.
IIRC, Fagin a petty criminal, so, odds are, he prolly had a warrants and couldn't go to the police, otherwise, he'd be arrested and, if he got arrested, who's going to take care of his dogs? On top of this, Sykes is a patient man and so will get after Fagin after he's out.
Dodger's Bandana
How'd Dodger get his bandanna back after the climax?
Fagin probably got him a new one. What I wanna know, is where the heck did his bandanna go during the "Why Should I Worry?" sequence?
The "Why should I worry sequence" was just a simple Animation error (Movie goofs; they happen. They're all over IMDb)
Syke's loaning practices
Why would Sykes even bother loaning cash to a bum like Fagin in the first place? Assuming he was always homeless, did Sykes really expect Fagin to pay him back?
Sykes doesn't care that Fagin's poor. He knows the old bum has got to pay him somehow.
The trouble with borrowing money from Loan Sharks is that you tend to end up even poorer than when you started, with fun things like 500% interest per week. Fagin may not even have been homeless until he started borrowing money from Sykes.
Apparently in an earlier version of the script, Fagin borrowed money from Sykes to bet in an illegal poker tournament, possibly to help cover living costs, before losing all of it. If we were to assume this was the same case in the movie, Fagin may have been able to convince Sykes that he would get his money back once he got his winnings.
Another thing to note, IRL, loansharks deliberately target people who can't pay them back (there's a reason they're called "loansharks" ofc), so Sykes' practices make sense to a degree, as Fagin is a desperate man and will do anything to stay alive. It's about control.
Jealous Georgette
Why is Georgette getting jealous of Oliver? Does she want the same kind of love Jenny is providing? Or does she just not like the fact that competition for pet attention is at hand?
The latter. Also, Georgette is a purebred showdog and Oliver is a mangy stray cat. Of course she's gonna disapprove.
Jenny, you should have called the adults!
Why did Jenny go ALONE (Georgette not withstanding) to get Oliver back? Didn't her parents ever tell her that there are some districts in New York that upper class children should avoid at all costs?
She's a kid, and wants her cat back, so it's not surprising that she'd risk it. Kids are less sensible than adults. And her caretaker, the only adult who could go with her, would most likely not let her go there at all, let alone let her use any of her father's money to pay the ransom for a cat that she didn't have parental permission to take care of in the first place.
Ransoming Oliver
Other than the fact that Fagin would have looked more cynical, why couldn't he just leave Oliver in Sykes hands and have HIM ransom Oliver back to his family? Fagin was rather worried that the "Cat owner person" was tough and strong, and was paranoid about the cops showing up too. So why not just leave Oliver with a REAL badass who'll show no mercy if he doesn't get the ransom money?
I really doubt that Sykes would’ve taken such an offer from Fagin that seriously. What evidence did he have that Oliver could be ransomed, a collar with his name on it? He could've stolen that off of someone else's pet and stuck it on Oliver easily. Sykes might've even suspected that Fagin was trying to get him in trouble with the law.
Also, even if Sykes and Fagin knew for a fact that they'd get a handsome ransom for the cat, Fagin can't just hand over Oliver and say "Hey, Sykes, why don't you take care of this ransom business for me? And then give me all the money?" Not even when Sykes knows Fagin will give him the money back to pay his debts. It's much easier, and safer, to have Fagin blackmail the cat's owner. Also, a good rule for a loan shark is never to accept valuable objects instead of money. If the objects are worth as much as the person in debt claims, you tell them to sell it for that amount and pay you the money. If they do, you get your cash. If they can't, then you were wise not to accept their offer.
It's also not that practical of a scheme to expect anyone to fork over a substantial amount of money for a cat that came from the gutter and was in their life for a very short time. Had Jenny's parents been home when the ransom note came, they probably would've just bought her another cat.
Both of these explain why Sykes would insist that Fagin play out the ransom idea. But then why did Sykes kidnap Jenny to ransom her back to her parents? There wasn't that much evidence that she had rich parents who would have the money to paid off every penny that Fagin owed Sykes. Jenny's own allowance only amounts to a piggy bank, like my middle-class childhood finances did at her age. Granted ANY parents would pay through the nose to get their children out of a life and death situation, but my point still kind of stands that Sykes technically shouldn't have expected the Foxworths to have such money either.
In that case... it's been a while since I've seen the film, but Oliver's collar had an address on it, didn't it? Sykes might've known that the address was from a well-off neighborhood, and was simply waiting to verify that Fagin's story checked out. If this was the case, once Jenny came along, he could've reasoned she belonged to a wealthy family who would pay through the nose to get her back.
the address on Oliver's collar says that the Foxworthy (Jenny's surname)live on 5th Avenue. It's one of the most expensive streets in the world. Foxworth Residence, #1125, 5th Avenue,
They don't need to be wealthy, they just don't need to be poor. Almost all families can get a small fortune if it's the only way to pay for their child's life. And those who can't pony up the requested money can often get you at least an amount worth the trouble. At any rate, they'll pay more for their child than they would for their cat. Most likely, Sykes figured that the cat wouldn't get them much more than what Fagin owed him. But a child? That's lots of cash. The kind Sykes would want to keep all for himself.
That idea prolly wouldn't have worked because 1) we don't know how Jenny's parents are in regards to pets, that is, whether or not they see pets as replaceable, 2), wealthy or naw, a kitten might not fetch that big of a ransom but a kid definitely will, and 3) considering how children fare in the hands of ransomers, Oliver definitely wouldn't have fared much better. On top of all of this, Fagin is a really nice dude, who'd likely not be able to bring himself to do it.
Syke's influence
Sykes was pretty heavily involved with the criminal underworld, and its implied that he was even associated if not a part of the mafia. So, wouldn't other unseemly individuals react badly to him being gone? Doesn't his death just place Fagin and the gang in even greater danger than before, or am I wrong?
Sykes was going to kill Fagin, and you can't be in even greater danger than that, right? So Fagin went from Sykes wanting to murder him to random mafia dudes maybe wanting to murder him. That's a small improvement. Not to mention that somebody else might take Sykes's place now, and not be too eager to off the man who made such a promotion possible. But yeah, people might get mad, but they've got no way to track it to Fagin in particular, let alone Fagin's dogs. Finally, Sykes died in a car accident, so the most logical conclusion is that he was driving drunk, or using the kind of substances you don't see in Disney movies.
The Reporters were asleep
Shouldn't the collision between Sykes' car and the subway train have made the news? Surely an explosion like that can't go unnoticed in the Big Apple. Even if nobody had smartphones in the late 80s to record it, the surveillance cameras for street traffic and businesses should have got a glimpse of it. And if anyone noticed the electric scooter driving down the bridge rails right after the explosion, they'd put the pieces together and somehow Fagin and the Foxworths might get into some legal trouble with the city for all those traffic violations, among other things.
I'm not going to pretend that I know how that would work in New York, but I'm pretty sure you won't get in trouble for traffic violations if you testify that you were being chased by a madman on a Cadillac who had previously kidnapped you/your companion.
The Third Day
Sykes gave Fagin three days (and specifically mentions three sunrises and three sunsets) to come up with the money he owes him. This happens during the evening, but let's break these three days down for a moment:
Day 1: Fagin drives the gang into town, and now mentions that they only have two days to "do or die". Jenny finds Oliver and takes him home. The whole "Good Company" montage happens and Oliver receives his collar.
Day 2: Jenny goes to school. The gang "rescues" Oliver from Jenny's house and bring him back to their boat. Fagin finds and attempts to ransom Oliver. This is clearly the deadline as Sykes sics Roscoe and DeSoto on Fagin when he fails to produce the money, and only gives him a twelve hour extension when Fagin explains his plan.
So, what happened to this third day? It seems to be immediately forgotten the moment Fagin gives his "do or die" comment. Even if Sykes considered "Day 1" to be the day of their first meeting, it's still bullshit because Fagin never got "three sunrises" to come up with the money. Granted, Sykes is hardly an honest person, and Fagin likely wouldn't have come up with the money even if he did get three full days, but how did Sykes' three day policy suddenly regress into two?
Either Sykes was just being dramatic with the "3 sunrises and 3 sunsets" statement, or since it was nightfall when he confronted Fagin at that point, he might have considered the first sunset that very minute. And the 12 hours was until the third sunrise. He only had his dogs attack Fagin because he visited empty handed. With that in mind Day 1 started with the sunset at the time of his first visit to Fagin, the other two days already have already been established, and the deadline was the sunrise at the 12 hour mark. Three sunrises and three sunsets CAN (And in the summer time DO) occur over a timeframe of LESS than 72 hours.
Now What?
What happens to Fagin and his crew in the end, now that they no longer have to worry about Sykes? Despite saving Jenny's life and stopping a ruthless criminal, do they return to living on the streets and barely getting by?
They are now on very good terms with the Foxworths, so I'm pretty sure they'll lend them a hand if they need one.
Do people just not like Orange Cats?
Why wasn't Oliver adopted in the beginning of the film like all the other kittens? Just bad luck? It'd have some basis in reality if he had a missing eye, if he were older, scruffy, mischievous, or even if he was a black cat, but as far as my knowledge goes, he just got unlucky.
I can't think of any in-universe explanation, but Disney would want Oliver to have a vivid orange color scheme since he's the main character and would be more marketable that way.
