Do you have a retail license to sell wine? If not, you’ll have to strike one word from the quote above.
Back in 1999, when the American Bar Association held a joint convention in Toronto with the Canadian Law Society, US Customs was on the lookout for lawyers returning from Canada with Cuban cigars and nabbed a whole bunch of folks.
I have a better version. My wife could buy the wine from me for $1/bottle. Pay the taxes on that when importing and then let me drink it all! Genius!
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Yes, last week. I brought back 20 bottles from Germany. Opened my wine suitcase and showed all the bottles. He didn’t want to hassle with checking each bottle for alcohol content so asked for the lowest one. I found one at 7.5% and he put that into his computer and came back saying I owed $7 and change and waived me through. I was told if it was over $20 I would have had to pay.
When in doubt, declare and they aren’t going to hassle with you. Many times though the declaration area at certain airports isn’t even open so you just walk through.
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There are other issues with his scheme related to fraudulent customs entry.
Does my version fall foul of that too?
Yes
Aha, I think I’ve fixed it with two strikes.
How about "He could then legally
buy
*drink
it all back
from
*with
me in the US"
@David_Bu3ker have I defeated customs yet?
Only if you pay tariffs on a legitimate value of the wine upon import.
The whole rigging a scheme between relatives, friends, etc. runs afoul of a provision in the customs valuation rules on “related parties” transactions.
If the value is not legitimate the goods can be seized/destroyed, and there are potential penalties for the parties involved in the scheme.
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I’ll stick to stateside Acker Auctions, then! 
get a cheap coach ticket to Europe and lug your wine back. You just need good luggage allowance so you aren’t overpaying for the bags. I was allowed 3 suitcases up to 70 lbs. Airline status certainly helps.
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I was in Europe twice this fall and no problem bringing wine I declared. If they are convinced that you are bringing it home for personal consumption they wave it through. On the other hand I know to bring back wine through Canada because the LCBO has trained their customs people to charge appropriate duties. I will stick with my duty free allowance coming through Canada.
Quick reminder to check the maximum amount allowable in your first port of entry into the US. For example, Virginia has a max of 3 Gallons per person.
Also, agents don’t seem to know how to add/multiply at Dulles. I claimed my 13 bottles, all of which were 750ml or less, a total of 9.5L. I got sent to secondary where after an hour…. Thankfully that agent had a calculator and sent me on my way.
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