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Re:The largest unknown Bitcoin wallet moved nearly $1B for $... by toss1 on Tuesday June 30, 2020 @10:53AM (#23690635)
depends on the nature of the transaction & the parties - 'transfer/transaction taxes aren't the only issue

Sales or gift taxes could apply. So could import /export taxes depending on the endpoints. Could it appear as income/gains to one party or another? etc...

of course it can often be structured to avoid such taxes, but it requires forethought.

I wouldn't even think of making a $multi-million move without first consulting a very high end attorney in the appropriate field.

Re:The largest unknown Bitcoin wallet moved nearly $1B for $... by sukilot on Tuesday June 30, 2020 @12:57PM (#23692110)
$Million is pretty simple. That's an everyday real estate purchase is a major US city. Tens to hundreds of millions is different. But even tens could be handled by any attorney in the field. That's estate planning level.
Re:The largest unknown Bitcoin wallet moved nearly $1B for $... by toss1 on Tuesday June 30, 2020 @11:57PM (#23697614)
As long as you have clean money with an obvious & documented provenance (i.e., how it was earned), and an obvious above-board purpose such as buying a house, sure, transferring a few million is likely to be straightforward.

But that is off-topic - the topic is anonymous transfer for unspecified reasons.

Even transferring between two accounts of different businesses you own can generate SARs (Suspicious Activity Reports) at $5K level. Even multiple deposits of a few $thousand in cash will draw attention & be subject to confiscation if you don't have a solid & documented explanation, such as running a big & legitimate cash business.