I think it would be safe to assume people in this high-flying financial orbit would have access to the sorts of people that could get them out of the country without a passport.
I suppose you could always try to pay a coyote, but, uh, that's a bit of a high-risk play.
Or you could drive into Mexico, but without actually having fuck-you money and connections (These two don't), you're not likely going to stay outside of the arms of law enforcement for very long.
And if all this works out, and you end up on the run, you now have to full-sever every connection you have to anyone you know. Not a lot of fun.
Manning up and just doing the 11 or 13 years in Club Fed seems pretty attractive, compared to all that.
Just look at the recent Carlos Ghosn[1] situation. Former USASF operators working as Private Security Contractors smuggled him out of the country. The plot involved what appears to be close to a dozen people too, and included falsifying passenger records on multiple international flights and more.
It would not be surprising if these sorts of folks squirrelled away vast sums for a "rainy day" in places that make it difficult for governments to get. Seems pretty standard operating procedure for people who are legit - not just fraudsters.
It's probably 2 orders of magnitude harder, in the long-term, to arrange for a high-profile American fugitive to use American mercenaries to abscond to another country.
I'm pretty sure there's thousands a day that walk into Mexico everyday without a passport. Hell half the people in line returning to the US claim they "forgot" theirs.
Leaving is easy without a passport. And don't forgot if Sunny can get to the shores of Pakistan, he is a citizen and they must let him in, after which he can easily hide in the tribal areas. All he would need is a yacht somewhere on the multi-thousands of miles on the coastline and some friendly boats in int'l waters to refuel him.
Someone like Sunny can't realistically just drive to and walk across the border.
There is a lot more to the DHS apparatus than simply scanning passports. Most of it is unseen by the public.
Now I know the government must surely have these systems but I think it may be doubtful how effective they've set it up to be to stop people leaving the country if by foot. The flow of people leaving the border in general is just way lower scrutiny, in my experience living in a border state. I would be shocked if the average say non-violent felon fugitive has much trouble leaving if they're not on a flight manifest.
How does the USA treat that in general? Do the people accept it, or praise it? Do they try to trick you into admitting legal problems with it? You can get back into the USA so I assume you must be a citizen?
What's your opinion on the general legality of fighting in a foreign war by choice?
Did you accomplish enough that you'd do it again?
Fwiw, you have scheduled flight plans and if a pilot did this deliberately they'd be reprimanded hard. You also have to land international flights in designated airports that have immigration. This wouldn't be easy to do if you're both wanted and bankrupt!