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I use to play a lot up in Vancouver so I am familiar with this question. I use to be very worried customs officials would steal my cash after hearing civil forfeiture stories. Especially when I first started playing. So, just like you, I really never wanted to declare. But it's important to know that customs officials rarely seize cash from people who follow the rules. In fact, I've never even heard customs officials (US and Canadian) seizing cash as long as you were honest with them. They have no reason to take your money unless you lie to them, or it's obvious it's proceeds of crime.
I've transported large amounts of cash ($50,000USD+) before in numerous currencies to and from Canada. It's not a problem if you are honest with them. Someone mentioned customs takes their job very seriously. That is very true, especially in Canada. Canadian Customers Officers, and the CBSA (Canada Border Services Agency) are some of the strictest, meanest, customs officials I have ever come in contact with on my worldwide travels. I have been almost everywhere, and do not know why the crazy canucks are the worst by far. I was taken to secondary screening last time after I declared all my cash and did everything they asked of me. They are very strict, I would not recommend playing any games with these guys, or trying to structure how much cash you have so you don't have to declare. Also keep in mind when you're going INTO Canada you have to declare anything over 10,000CAD not USD. So your example of $9000 would actually have to be declared as it's over 10,000CAD. In fact $8100USD is over 10,000CAD so you'd even have to declare that!
Border agents are not known to seize cash the way Cops in America do. You really only have to be nervous and worried in places like Oklahoma, Illinois, or other highways used to ferry drug money that you happen to be driving on with a lot of cash.
I would recommend bringing over the border however much you want to bring, and declaring should you need to. Save bank receipts, casino receipts, and any other receipts you can gather that you can present to the border officers should they ask how you got the money. But be completely honest and straightforward with them. Don't be afraid to tell them you're a professional gambler. Even if they give you odd looks, and repeat what you just said in a surprised tone. They will do that no matter what your answer is to see what your reaction is. Be honest! Do not make up any stories. Also, just a tip I learned, the money is 10,000CAD/USD PER PERSON, not per vehicle. It's very hard to find the answer to this question, but I finally did when I just asked them. So if you're traveling with several people, it depends on how much EACH person has on them.
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