Bearer bonds are a real thing, but the US government no longer issues them.
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- Become Immortal.
- Demand the ransom be converted to gold and gems and buried in a desert tomb.
- Wait 1,000 years to collect. By that time the heat should be off.
A Twilight Zone episode covered this. When the robbers woke up from cold sleep the gold they’d stolen became worthless.
Dare I suggest … BitCoins?
Step 1: Demand that the ransom payment be sent to one of your BC addresses.
Step 2: Use the Silk Road to convert your BitCoin into illicit goods, and, ultimately, into hard currency.
This has the advantage that you are not linked to any particular physical location.
As a bonus, make sure you invest heavily in BC before you make your demand. The press coverage from the ransom should make BC shoot up again in value. SELL SELL SELL! Ultimate pump and dump. Hell, you could even return the ransom and still make money.
Choose a commodity that is compact, untraceable, and durable. Easily transportable by one person in no more than a duffle bag. Uncut diamonds for example.
Have the package dropped from a helicopter into the bed of a truck parked on the roof of a multistory parking garage for a large hotel or shopping mall. I have previously arranged to have any security cameras in the garage be either defective or looped.
Drive down one floor to be under cover and dump the payoff into a Faraday bag to foil any active or passive tracking devices.
There are multiple exit strategies from here.
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Immediately transfer loot to another vehicle and join the regular traffic exiting the structure.
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Stash the loot in a prepared hidey hole to pick up later and just leave.
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Take the payoff and go into the mall/hotel and leave by another exit.
That’s clever 
but the only problem is that I presume it would be traceable for any significant ‘ransom’ by tracking who short-sold GM in significant amounts and is not a well-known trader.
And, of course, it’s not really a ‘drop’ as per the OP.
Do what D. B. Cooper did…
I thought the best criminals e.g. drug lords are those who live in plain sight, but are untouchable? Prove that you can make bad things happen, but they can’t be connected to you.
I could tell you the perfect system, but then I would never be able to use it [del]again[/del].
Ah, but if I am immortal, I am not sleeping the entire time. I am alive and aware of what is going on in the world. I can pick up the treasure any time it is conveniently unguarded and/or forgotten.
This isn’t bad so long as the authorities don’t have time to prepare. It adds a layer of complexity, but if you arrange the drop to be somewhere else and
collect it with a UAV, then do the drop, you should be able to lose yourself in the traffic.
I had thought it was understood that minimizing the time they have to prepare was parts of everyone’s plan.
The first part of their instruction is to have them have the payoff in a helicopter at a specific time. At that time, call them and have them fly to a point that’s not the dropoff. They’ll start their ground units to that point as well.
When the courier gets near or to the first point, call them with a second dummy drop. Lather/rinse/repeat 4 or 5 times. Then send them to the real drop and with the last call, tell them to drop the bag in the back of the red pickup on the top level and leave.
The post drop details from the first post can be accomplished in 2 minutes. Barring extraordinary bad luck there’s no way any pursuers can be there in time to catch anyone.
And even if they do, I’m not going to be the one making the pickup. If they do manage to grab the minion my next call will be to give them a choice. The ransom just doubled. Or the ransom remains the same and I detonate one device to express my annoyance.
I like it, but there are potential problems.
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Disabling the cameras in the garage is probably not going to be as easy as it looks in the movies. You might be able to defeat surveillance some other way though; use a garage with automated payment, wear a disguise, and put fake plates on the getaway car.
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If you’re going to ditch the red pickup at the scene, you have to make sure it can’t be traced back to you.
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Garages like this are typically in urban areas; that means police nearby who can be called in on short notice and bystanders who might take an interest in a helicopter flying low over a parking structure.
Could we keep the basic idea, but move it to someplace more isolated; a wilderness area with a tunnel nearby, or just lots of tree cover, perhaps? You lose the advantages of having multiple exits and lots of traffic to blend into, though.
Ideally, you’d want to make it look like you died in the getaway attempt and the loot was unrecoverable. But that introduces a whole lot of complications.
For one, there aren’t too many places where loot becomes unrecoverable. One though, is the Mariana Trench.
What if you made the drop off point somewhere on the sea above the Mariana Trench and the courier has to meet you there. You have a floating buoy there that carries a big metal box, into which the ransom is to be delivered. The buoy emits a signal so it’s easy for the courier to find. You also have a motorboat a few hundred meters away from the buoy, which the courier is told not to approach. The box on the buoy is attached to a tow-line that is connected to your motorboat. You are on the motorboat giving instructions to the courier.
You instruct the courier to put the ransom in the box. Once it’s done, your boat takes off dragging the submersing box behind it on the tether. But before your boat completely leaves view of the courier, it catches fire and explodes (via your remote-controlled detonation). Oh, did I mention that you are not on the motorboat? No, you are somewhere else. There is a corpse on the boat though, which you stole from a graveyard or mortuary several days earlier. Also, the box was not directly connected to your motorboat, but was actually connected to a long-range torpedo that was attached to the bottom of the boat. When the motorboat explodes, the torpedo detaches and dives, towing the box behind it and on to it’s new pre-programed heading - which is away from the Mariana Trech - somewhere where you can pick it up later.
CONS:
- Expensive and complicated.
- A lot could go wrong with the technical elements.
- You can’t inspect or verify the loot before you take it (so it may be bugged).
Predicated on your OP assertion and my real world experience:
Assertion: “Also assume that you have significant, but not unlimited, resources of your own to travel and collect the ransom.”
Experience: Video security systems.
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Parking security is the last to be upgraded and maintained. While the rest of the facility will have been upgraded to high definition networked cameras, the parking garage will still be on coax lo-light. High value targets like casinos are the exception. Even if the cameras have been upgraded to digital the wiring is usually exposed and subject to compromise.
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Hotwire a vehicle that’s already on location. I’ve already scoped out the site and know which truck belongs to an employee that won’t be missed until they go off shift.
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What? Parking garages are associated with locations that have large customer bases and have the capacity for hundreds, if not thousands, of vehicles. Hotels, casinos, hospitals, malls, business buildings. Most of which are in business or industrial districts.
Go ahead and shift to an isolated area, but you lose the advantage of overloading the resources of whomever is monitoring you. Thermal imaging renders most foilage invisible. Tunnels have one entrance and one exit. Setting up a roadblock to search every vehicle is going to piss a lot of people off, but you’ve trapped yourself in a hole in the ground. Pretty sure the authorities are going to have any access tunnels covered as well.
Why doesn’t Kim keep the whole thing when his guys board the boat?
For comparison, at today’s market prices, a million dollars of gold weighs between thirty-five and forty pounds, and takes up 846 cubic centimeters, or 28 fluid ounces, or enough to fill just over two beer bottles. (Wow! I knew gold was dense, but that’s a dramatic way to put it.) A million bucks in gold, therefore, is easily carried in a small backpack, or in a visibly heavy but carry-able briefcase. Two million in gold is about the limit of what a single man could carry quickly, and that would probably have to be strapped to his back somehow.
I think your method is reasonably sound, but vulnerable to random chance with the bystanders. There will be people in a position to observe (and record with phone cameras) the attacks on the cameras, the helicopter drop and the transfer. We also have at least one known crime scene (the initial vehicle) that you’ve got no opportunity to sanitise.
Overall a good chance of success, with small but not insignificant chance of being traced afterwards.
The idea of the tunnel was to use it to change cars. You’re probably right that wouldn’t work. Too much traffic and someone will see you make the switch, too little and it will be easy to tell which vehicle you’ve switched to. And for safety reasons tunnels are probably more heavily monitored with cameras than garages are.
I have always wanted to write a story about destroying a big insurance company by using terrorist extortion to force them to invest their reserves in worthless instruments, like Zimbabwean government bonds. Since the goal is not personal enrichment, but achieving a socio-political goal, there is no direct contact between the perpetrator and the ransom; the money simply vanishes into an economic vacuum, and the victim suffers the consequences.
Maybe you hid one of the bombs under his palace.