I think you have four issues:

1. How to do it, with the security. Honestly, I think with Trump it’d be easier than with other presidents, because he’s a fucking moron who doesn’t listen to experts
2. How to get away. I think this may be the most difficult part, since you have to flee the country and make your way somewhere relatively safe
3. How to prove to Iran it was you
4. How to enjoy your gains, with what would be probably the largest manhunt on the planet likely through to your death

DB Cooper proved 2 and 4 are not impossible, although technology, forensics, and surveillance have drastically changed since Cooper, and I subscribe to the theory that he didn’t survive to spend the money - not only surviving the jump into dense forest, but then trekking out of deep wilderness to civilization were both challenging obstacles. Anyone who’s been through a parachuting course knows the last place you want to land is into a bunch of pine trees (Ok, water can be pretty bad too, but still).

I digress. Assuming you can pull off 1 and 2, and assuming Iran’s not just going to ghost you, 3 is sincerely a difficult problem. How do you contact the right people in Iran? How do you prove it was you, without the support of US intelligence? Maybe some GoPro footage, routed through a scope? Would that be enough?

But I’d be most worried about 4. I can’t imagine enjoying life constantly looking over my shoulder, and even then, there’s no defense from a sword missile once they’ve ID’d you. So you’re going to, what, hide in Iran for the rest of your life? Depending on your race, your options could be limited merely by how much you stick out - a rich white guy living like a king in Papua New Guinea. Maybe try to buy a new identity and continue living in the US, hoping the IRS doesn’t take an interest in you?

It might be accomplished by a terrorist group, planned and tracked hand-in-hand with Iran for verification, via a disposable fanatic and with funds going to the group upon completion. But I think if they could pull that off, they would have already. Terrorist groups tend to be a sledgehammer, rather than a scalpel: effective against unprotected soft targets, impotent against hardened ones.

I think of someone gets Trump, it won’t be for a bounty; it’ll be for ideological reasons, and they won’t expect to survive it. Heck, with the Patriot Act, I wouldn’t want to survive it, b/c they may just decide to torture you for the rest of your natural life and Americans signed away their rights to due process after 9/11. It’ll be another Thomas Crooks, only a better sniper, or some novel approach like some tech coming out of the innovations being developed during the invasion of Ukraine. If I were the Secret Service, that’s what I’d be terrified of. There are some intensely smart, innovative people in Ukraine figuring out fantastical ways of eliminating people, and I think we, the general public, are seeing only the most mundane, oldest examples of what they’re using.

McDonald’s could claim the money after his massive coronary due to his Big Mac addiction.

They wouldn’t even break in to get you. They’d just bomb the six areas you might be hanging out in

So they would be rich the rest of their life?

Pretty much my assessment.

I can have 80 million dollars but I have to live my life in constant fear and in Iran.

You probably don’t want to stay in one place. The US would quickly lob a missile to wherever you are. $80m probably wouldn’t make up for being on the run for the rest of your life in a country that will probably be turned into a war zone.

I mean they might pay, but probably not 80 million. And most likely not a lump sum.

Maybe they’d give you a hideout with a decent allowance every X days, and you have to promise to to never criticize or insult their government, and any internet/phone access will probably be monitored (by the Iranians).

And its not gonna be because they care about you, but just to keep you alive as their pet because its kinda like a middle finger to the US. But you are just a pet to them, not some hero.