I don’t equate grey market with bootleg. The difference in copyright laws allow grey market to happen which means the rights owners aren’t being compensated the way we would expect.
Bootleg means it’s unauthorized and the rights owners were never compensated.
I wish rights owners wasn’t the way I have to phrase it. I could give two shits about Blue note
Making more money off of every album, but if the artists were getting proper compensation, I would be happy.
In practice, the difference is not very relevant.
Grey market means you have a recording that has lapsed into public domain. Neither the artist nor label, or music publisher, gets a dime.
It should be noted that a recording may be public domain, but the master is owned by the label/rights holder and always will be.
Also, a 'remaster' renews copyright, as it is not the same work that was originally issued.
To make it easy, there was a legal case a few years back over Beatles CDs that were being sold in Walmart which were 'grey market', the contention being that they were public domain. In fact, the company that pressed those CDs won the case, because they used needle drops of the original vinyl - which are public domain. The later CD reissues are not, and had they used those, they would have lost. They did have to pay the publishing company, though, and song copyright is different and longer that recording copyright.
Either way, neither the artist nor the record label have authorized it.
Bootleg is generally the publishing of a performance that has been obtained or recorded without permission, or an unauthorized publishing of a work that is still under copyright. Again, the artist, label and publisher get nothing.
Most bootlegs are illegal pressings taken from a CD still under copyright protection. Labels like Waxtime operate in countries where prosecution is lax.
I also don't give a rat's ass about BN making more money. Bear in mind that the artists on BN were paid session fees and get no royalties from the recordings. Never did. That is why songwriting credit was so important back in the day, that was the only long term revenue stream.