This is crazy because I did not get this impression at all. Being rational and clean-cut and descriptive does not an asshole make. I mean seriously, if THIS is your definition of "asshole..."
But I can't help but now wonder if his mere being just triggers vastly different things in people unfortunately (such as instant hatred of "tech elite" by SFPD cops in the San Francisco piece he wrote).
Try spending even a night in a U.S. jail, or worse yet, any considerable amount of time in a US jail while awaiting trail, and ONLY THEN can you appreciate how easy he got off. Before reading the article, my gut told me that he was going to get it much harder in Russia. I was surprised to find out how humanely he was treated compared to the way we treat suspects/inmates in the U.S.
He's actually a really nice and interesting guy around a lot of SF communities. He has definitely traveled a lot and has tons of other great stories too.
The "situations" in the first part of the story, I felt like he was just acting strategically and smart (impressive even, I'm not quite that forward-thinking). Because he did't know yet if these people are helpful or just trying to screw him out of as much $100's as possible and then let him hang.
But after the rest of the story, those guys helping him, drinking with him, showing him a good time (probably because life can be boring there and hanging out with a foreigner was an enervating experience for them too?) and greasing a few wheels for him (the "lenient judge" and possibly some other things he doesn't know about), I felt a bit different.
He was carrying $160 all the time, while Irlan paid for everything (probably not very much in dollars, but still). Some guy needed a spot for $6.5 to carry him to the end of the month, that says something about how far $160 goes in that country. At the end when Irlan said "it's gonna be boring without you", he knew he was free and could have wired himself another $200 later with relative ease (or maybe not? I'm not sure). I think at the very least he could have given Irlan some money/tip for all the effort, lunch, coffee, drinks? I mean, now that you know you're no longer in a complex negotiation / bribing situation with this person (so the cards are more open), he did go the extra mile, spent his own money even (while in the end, the author spent .. $0 ??? or did I miss something, he did say he got the $100 back). Say $50, that he'd otherwise spend on a single night out in SF, would mean a LOT more to this guy, so why not just do it? He'd earned it yes?
Could be some kind of cultural differences though. The author seems to know the culture of the area really well, so maybe it's something obvious. Maybe Irlan would be insulted getting such a large sum for just being hospitable. OTOH maybe Irlan hoped all this extra effort would earn him the $100 deal he couldn't fulfil earlier. Or maybe during all the "bonding" the author had been hinting he was a stranded student with zero money left and therefore they felt pity on him, so he didn't dare to break that character and suddenly producing $50 cash to give away (but Irlan knew he still carried that $100 at least).
Or maybe, the author's bottom-line thinking about this was, I did my best to stick to the (admittedly, draconian) rules, bad shit (aka adventure) still happened, so I really oughtn't face any consequences at all (except the part where he got free lunch, drinks and a tour).
But I can't help but now wonder if his mere being just triggers vastly different things in people unfortunately (such as instant hatred of "tech elite" by SFPD cops in the San Francisco piece he wrote).