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.