It may seem a bit presumptuous to question how Edward Snowden has conducted his affairs so far. After all, he is still alive and not in the tender care of the so-called American justice system, despite having crossed the surveillance arm of the world’s only superpower and fomenting multiple diplomatic uproars. Of course, the irony is the scandal ought to be about the conduct, but America’s putative allies are and probably remain fully on board with the “all spying all the time” program. It’s the nasty bit that their citizens were kept in the dark about the extent and intensity of the snooping and many of these countries pretend to be functioning democracies. And the spectacle of tech companies too often happily selling out their customers for a little DoD intelligence isn’t too pretty either.

So the political part of Snowden’s project seems to be going as well as he could have hoped. He’s made clear that if something were to happen to him, the revelations would continue, which suggests he’s either handed copies over to the Guardian or arranged some sort of fail-safe. And if the Guardian does have a full set of what Snowden took with him, he’s effectively ceded control (as in were Snowden were to have a change of heart, he couldn’t prevent the Guardian from continuing to publish). Snowden has even managed to stir Le Monde to publish its investigation of the French intelligence services, which has created more consternation.

But it isn’t clear Snowden has been as adept in his personal affairs of late. Admittedly, anyone commenting on Snowden’s movements has only a very limited vantage. But his first gambit, going to Hong Kong, was brilliant, for the reasons recounted by MsExPat, including: he’d be safer there than just about anywhere (the US wouldn’t dare try rendering him and even assassination would be difficult); the legal system is very slow, careful, and deliberate; and he’d have tons of superb lawyers falling all over each other to represent him for free. The one risk was that Beijing might relent and decide to tell the Hong Kong authorities to extradite him, but most commentators thought that would make a mockery of the special standing that Beijing was keen to maintain for Hong Kong, and would also look like Beijing bowing to US wishes.

So why did he leave? One school of thought is that Snowden was given word quietly that Beijing was increasingly uncomfortable with his presence and he’d better get out while the getting was good. But I’m persuaded by MsExPat’s theory, that Snowden fell prey to a massive cultural misunderstanding. Remember, as smart as he is, he was only 29 and has almost certainly not had much experience hiring or managing lawyers, particularly on something high stakes and cutting edge (dealing with lawyers on novel legal matters can be particularly trying). Her assessment:

It’s looking like Snowden’s decision to flee Hong Kong was a hasty, and bad one. Based on my experience with Hong Kong lawyers, I suspect he panicked–the legal style there is to sit down with a client and then lay out in excruciating detail all the worst things that could happen to you during the progress of your case. This can be quite scary. But the actual reality usually turns out to not be quite as bad. At least one Hong Kong human rights lawyer thinks Snowden might have emerged okay from Hong Kong’s legal process: “He obviously chose to go to Moscow, though I don’t know why. I wouldn’t have,” said Patricia Ho of Hong Kong law firm Daly & Associates, who isn’t involved in the case. She said Mr. Snowden had had a range of options still open to him before he left Hong Kong, including filing for asylum or contesting the U.S.’s request in the city’s robust judicial system.

Remember, this is almost the polar opposite of the style of most US professionals, which is to sound super reassuring and if they have bad news, to dribble it out interspersed with what if anything might be done.

Now I am getting more speculative, in the spirit of encourage knowledgeable readers to pipe up. Snowden had other ways to exit Hong Kong, whatever his reasons. Lambert’s favorite is to Macau and then to Hanoi via ship and then to fly from there; he apparently considered leaving to get to Ecuador via Singapore. He also appears to have relied on Wikileaks for advice. This does not appear to have been wise. Readers are welcome to correct me, but to my knowledge Wikileaks does not have a lot of experience in dealing with litigation or asylum cases (one case, Assange, does not make you seasoned, and even then, what you had learned would to a significant degree country specific). And some of its litigation calls look awfully questionable.

The other valuable service from an attorney would being able to make contacts with the diplomatic community. Wikileaks was able to effect that with Ecuador but then alienated them with the row over the unsigned safe conduct pass. It is also not clear how good Wikileaks contacts are outside Ecuador. Remember that Wikileaks released a large trove of diplomatic cables. Yes, they were US cables, but the revelations often embarrassed foreign diplomats. So it’s not hard to imagine that they don’t have a lot of friends in that world.

The fact that Snowden flew to Moscow and was apparently planning to continue to go on to Cuba but didn’t (recall the empty plane seat and the Wikileaks representative going without him) suggests some element of their plan was found to be awry after they took off (did they not anticipate that his passport would be cancelled? Or were they worried about having their flight route changed and being forced to land in a country that would be willing to detain and extradite him?).

There are two important things to remember about Snowden’s position in the transit area in Russia. First, Putin has taken the position that it isn’t Russian territory. That means he can’t eject Snowden. Second, Putin has also said, loudly, that Russia does not have an extradition treaty in the US and does not extradite people (this is why continuing US demands that Russia extradite Snowden are either deranged or playing to the American public).

That should mean that Snowden can stay in the transit zone as long as he wants to (or at least as long as he can fund staying there). True, Putin has cleared his throat recently and said it really would behoove Snowden to get his act together and get out. But Putin also seems to be very big on his manhood. Having made such definitive pronouncements about the status of the transit zone it would be a big reversal to act otherwise.

So what is Snowden’s immediate problem? It seems to be 1. Flying over countries friendly enough to the US that might do to him what they did to Evo Morales, force a plane landing and 2. Having to enter a country in the course of his travels when he has no passport or travel documents. But the latter can be waved; I know people personally who managed (I am not making this up) to get to an international destination with no passport and eventually get in (admittedly a few hours of discussion, very elaborate examination of all luggage, but ultimately, an influential local vouching for them was sufficient). A long Reuters story did find some options: flying on a commercial plane (they have the right of overflight without permission; by contrast, government planes like Morales’s need consent), flying to Tehran (but where do you go from there?) or going over land for part of the trip (but Russia’s fingerprints would be on that). Maybe Snowden needs an official Venezuelan litter to take him to a Venezuelan car and then to the embassy in Moscow to at least get him out of Putin’s hair for now.

MsExPat also suggested that Snowden could reboot from Hong Kong (and one would therefore think transit through it):

Snowden could go back to HK: Mr. Snowden could return to Hong Kong, Ms. Ho of Daly & Associates said, attempting to apply for asylum after he arrived from the Hong Kong government or the UNHCR. The Hong Kong government has asked airlines to bar him from flying there, but he could get around that restriction because Russia would be “returning” him to Hong Kong, which would be different than “allowing” him to fly to Hong Kong like a normal passenger, she said.

He might hitch his commercial flight from there…and there are some routes that even passenger planes take that might work (HK-Johannesburg-Sao Paulo-Panama City-Caracas).

But the point here is not to try to solve Snowden”s problem, simply to suggest there may be ways to delicately tiptoe though his current boundary conditions.

What he has instead tried to do, however, is relax a big constraint, that of not formally entering Russia. But here’s where I start to have big doubts.

By having a press conference, Snowden gone about seeking aid in the most public manner possible. He’s basically thrown himself on the kindness of strangers, and we know how well that worked out for Blanche DuBois.

Russia has taken the official posture of being not happy that Snowden is stuck in the transit zone (whether it is really not happy is an open question). If Snowden could have found an intermediary (I would have gone back to Hong Kong contacts and tried daisy-chaining through the UN mafia; there would be decent odds of people in those circles being seen as being fair brokers), they could have tried to work something out quietly and maintained as much deniability for the Russians as possible. It would be important to take the position that Snowden was prepared to remain in the transit zone indefinitely; i.e., his departure entails risk to Snowden (true) and is thus doing Russia a favor (true), therefore they should want to help (at least up to a point). But the best way to explore options for both sides would have been quietly (and remember, even then there may be no mutually satisfactory solution).

Now it’s possible Snowden tried that and was rebuffed, but I rather doubt it (he’s not been there all that long, and his negotiating position would be considerably weakened by seeming keen to get out. He’d need to act like this is better than being in a US prison, so he’s prepared to hang out until he’s sure he can get out safely).

Instead, Snowden rounded up a bunch of people, most of whom are not on good terms with the government and asked for asylum (when all he might need is something that sounds like a less big ask, like safe conduct to the Venezuelan embassy, so he’s at least not rattling around the airport and technically not Putin’s problem). I find it hard to think of a clumsier way to have gone about this. From the Financial Times:

Edward Snowden, the fugitive US whistleblower, told Russian human rights activists, lawyers and politicians assembled at Moscow’s Sheremetyevo airport on Friday that he would seek asylum in Russia… In addition to human rights figures, there was one parliamentary deputy from President Vladimir Putin’s ruling United Russia party in attendance….. Most of the human rights groups invited to attend have been subject to searches and raids by law enforcement agencies in recent months, and told to comply with a new law requiring them to register as “foreign agents” or face punishment.

Snowden apparently e-mailed them all the night before, and it appears there were no official intermediaries or introducers; many recipients though the message was a spoof. Even though some Russian parliamentarians made supportive noises, the FT noted:

Mr Snowden’s request will put Mr Putin in a difficult position, in which he cannot appear to be caving into US pressure, but is anxious not to allow relations with the US to slide further towards confrontation.

Snowden may also not understand Putin’s conditions. Putin was clear that if Snowden were to come to Russia, he’d need to stop “damaging the United States”. That at a minimum means no more leaks. But if my earlier assumption is correct, Snowden may not be able to guarantee that, at least for very long. And the US clearly has a different view of what “damaging” is than Snowden does. The US thinks that anything embarrassing to the government is damaging. Snowden criticized the US not only for denying his right to seek asylum under the Universal Declaration of Human Rights but also for forcing the diversion of Evo Morales’ plane. Um, when you are a supplicant and you are already too controversial, best to keep the noise level down.

It isn’t clear whether Putin’s notion of what “damaging the US” constitutes is closer to the Snowden or the US position. The Russian deputy who participated in the meeting, Vyachelsav Nikonov, took a very Snowden-like view of the matter, but that does not mean this interpretation will prevail:

Any harm he did to the US was all in the past. What journalists are blowing up now is not his fault. Second, [Snowden said] that he has no intention of hurting the US as he is a loyal citizen.

In other words, it looks like Snowden is proceeding with no or minimal advice. He’s already cornered, but not having good guidance will make it even harder to find a path out than it would be otherwise. It would be better if I were wrong, and we probably won’t find out what transpired any time soon, if ever. I hope the “temporary asylum” gambit works, but doing it in such a high-visibility manner is unlikely to improve Snowden’s odds of success.