Lyric discussion by shwagga 

Cover art for Deal lyrics by Grateful Dead

I feel this to be about making careful decisions that don't result in a win or a loss for anyone, because a win for you is another man's loss. Such is the nature of gambling, you have to value yourself more than someone else in order to feel good about taking their money. I doubt this is an anti-gambling tune, but the first line "it costs a lot to win and even more to lose" speaks a lot to this negative view of gambling, but the tip to "watch each card you play" certainly doesn't discourage gambling.