Errrm, not sure about that. There might be a problem with the fact that your HDD is formatted for your Amiga, and your USB controller won't have a clue what's its looking at!
The best way for transferring files is to link the two machines together with a network, keep an eye out for a 3Com 3C589D PCMCIA network card - There's Amiga drivers for them and they work great!
Other possibilities are CrossDOS (I assume your already aware of this...), parallel or serial link with one of those USB adaptors (From what I've heard the adaptors aren’t all that reliable...); and then there’s a Subway to allow you to use USB on your Amiga.
Merry Christmas,
Hodgkinson.