If one were to win significant money offshore...

What would be a practical way to get that money into their US Bank?

Option 1 would be to simply take a big check and deposit it, and of course claim it as gambling income

What would be option 2?  That is if one were of a more libertarian mindset, and wanted to circumvent Uncle Sam?  What is the practical way to do so and not raise any flags with the banks?

Please only reply if you have some real knowledge of the matter.  I'm curious to see what some practical opinions would be

What do you classify "significant money" as?

Assuming over 5 digits?

Depends on the book.....

Depends on the book?  I play currently with 5dimes, and I have an account with Bookmaker.  I'd play elsewhere it it where an A+ book that can help me to get cash to us banking account.

Significant money as in 5 to 6 figures...

Since you have "six figures" purchase a small property in costa rica and collect "rent money". From your costa rican bank account send that to your. Us bank account and pay the applicable tax. But that's called money laundering so you may want to ask your defense attorney about it.

Another way is to open up a corporation on U.S soil take advantage of tax breaks afforded by corporations open up a small business unit under the corporate name (i.e. Mt Dew is part of Pepsi co) set base of operations is in a foreign country corporation claims the money and the tax hit will be less but not zero , you'll never be able to move 6 figures to a bank account with zero tax implications besides getting it in a big bag on a plane have the plane fly over your house before landing and drop it and let it parachute down take bag of cash and incrementally deposit at bank.