I understand that winner may have started with a small amount and got very lucky and gambled a lot of money. But we are talking about a long standing amount of gambling, not like he gambled once and got lucky, we are talking about him gambling thousands every month, that is a lot of money.

This is why it is a shock to many people and most of us have hard time believing this dude started with a few bitcoins at best and managed to reach to 4000+ bitcoins wagered, that is still in the possibility of what could happen, but we are still talking about something that would require a few miracles in a row. Obviously you know what you are talking about and we do not, you can see what he deposited and we do not, which is why we can't say this happened or that happened because we all would be guessing it. However you should also realize how hard it is for us to understand something like a few bitcoins turning into few thousand bitcoin wagering.
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I think I would not be able to make a bet of 400Bitcoin, it is that only with a fraction of 4 Bitcoin is already too much, a person who makes this type of bets must be a whale that has a lot of bitcoin, you must have a lot of security to risk losing So much money, that type of player that I admire, just thinking about betting that huge amount already scares me. Although Freebitco.in gambling is so easy and makes you play and play, I think the player just got carried away by adrenaline.