The Dread Pirate's curse is that he'll never be able really spend much of this pile of currency that he's accumulated, at least not without drawing attention to himself and getting busted.
History has shown that these guys eventually get busted but rarely for drug dealing; it's usually the IRS that busts them for tax evasion. If you're buying fancy cars, big houses, yachts, or businesses, eventually someone is going to catch on and follow the money trail.
I imagine in a year or three he'll settle down and live like a king in Patagonia :)
Regarding the money exfiltration, from what I recall, there are several money laundering "consultants" active on SR, there was a relatively recent interview[1] with someone who goes by StExo there. As with any illegal market, there are parties of varying levels of sophistication, from the guy who sells $100/week of weed to large organised groups with tens of members, drop houses, front companies, etc.
The (comparatively simple) problem faced by SR is converting BTC to hard currency. The harder part that both large SR vendors and physical drug traffickers have to contend with is obscuring the source and getting it onto the books as legitimate income they can pay tax on and pay themselves wages/dividends/whatever with.
But that isn't a new problem, and organised crime has clearly been doing it at scale for a while, and I can quite imagine professionals in the financial and business sectors who specialise in getting away with it.
It's worse. BTC transactions are eternal and only one really expensive bit of big data shuffling away from being fully mappable as they touch named real people. So as this guy spends BTC, he's leaving footprints, narrowing the search space by connecting himself to things and to people. That metadata is very likely to be what outs him.
From all the online busts I've seen since Shadowcrew busts and countless other illegal forums and markets after it the #1 downfall was letting federal agents become co-administrators and worm their way into the fold. From there they can engage suspects in supposedly confidential/trusted chatter and find out everything there is to know about them. Criminals love to brag and talk their way into jail.
This is easy to do. As a federal agent, sabotage the market with spam, ddos or security breaches, then be johnny on the spot with the solution offering your helpful services. Gain trust, engage in talk, bust everybody.
Depends on the country you live in, and whether you're willing to relocate to spend your money. A lot of countries will look the other way if you invest a reasonable amount of money into developing their economy or people.
There are also many, many ways of laundering your money.
Well if there asking him questions chances are already following transactions, and its very easy to tell if coins have been mined and maybe shuffled around a few times vs coins with long blockchain history.
Sure, but only up to a point. How are you going to explain how you mined a billion dollars worth of Bitcoins? What equipment did you use for that? Do you have receipts? How did you pay for /that/ equipment?
I agree with the previous reply that he might find a nation to shelter him but the US government is going to do anything they can to get at him there. Look at the success we've had in shutting down al Qaeda's financial arms and seizing their assets worldwide. If the US government can't get at his money directly, it will assert tremendous pressure on someone who can.
History has shown that these guys eventually get busted but rarely for drug dealing; it's usually the IRS that busts them for tax evasion. If you're buying fancy cars, big houses, yachts, or businesses, eventually someone is going to catch on and follow the money trail.