In this casino story they already had a 6-person SWAT team flying high enough not to be detected, above the helicopter doing the planned cash drop. While the solo helicopter pilot was a special agent armed with an MP5 and night vision, and a bag with fake $3 million of bills and every intention to catch or shoot the guy picking up. All of this was organized while the timer of the bomb was ticking down.
Given the low odds, it's boils down to an over-complicated suicide mission, with high risk of it not working out. Nor any point even if does. With the financial system also under a ton of surveillance and the involvement of his family and even one of their girlfriends.
It's no wonder that this sort of thing has become a rarity even for the clever ones like this guy.
It is very much a hypothesis, but it certainly could be true.