If you know you have a gambling problem, I would not start the status match at all. You will get some free play money, so you might as well play with that since it is free. In fact, you don’t have to gamble a single penny to make any of this work. I will put down a little money on a roulette table every once in while or try my hand at a card game, but I tend to be risk averse when it comes to losing my money. You might think a casino status match must mean I gamble a lot. How did I get here? Through the casino status match merry go round. If you had told me last year that one $95 annual fee business card could end up getting me 50+ free nights of travel including several free cruises, I never would have believed you.īut now here I am with two free cruises so far, several free nights in Atlantic City and Las Vegas, a free stay in the Bahamas, and more.