This assumes perfect opsec: the guy is unphishable, has a quick-response switch to wipe their computers when their house is raided, etc. They get a lot of people through simple gaps: bust the door down when the target is in the bathroom, grab the unlocked computer in a public setting, etc.

The other big assumption is that the only copy of the key belonged to someone in the gang who is a high-value target. If it’s an exchange, they need to make an official request. Someone offering laundering services or a lower-value person in the gang, the offer is likely going to be offered a plea bargain for cooperating to get bigger fish versus a much longer sentence.

Even if it is the most culpable member of the gang, the prospect of a very long prison sentence versus something shorter is going to weigh heavily — especially if you know that they’re just going to leave you in jail until you give them the key anyway.