[micwawa]

Is the tax something that a hedge fund with offshore shell companies and other active investments could work around?

[irixusr]

I seem to recal that Canada doesn't tax winnings.

And there's a better strategy then playing every number; play only the numbers that are not likely to cause a collision. You might not an every time, but you'll increase EV

[tempestn]

Canada doesn't tax winnings in games of chance. If you're seen to be operating a business though - a professional poker player for instance - the winnings will be taxed. Buying all the numbers to a lottery with an expected profit could definitely fall under that umbrella.

[bryanlarsen]

Under that scenario, you'd be able to deduct the cost of the tickets as a business expense.

[tempestn]

True. Would still reduce your net profit though. (And if your plan fails and you don't make a profit, I can just about guarantee they won't allow it to be classified as a business with deductible losses.)