What does, “play stupid games, win stupid prizes” mean?

Play stupid games, win stupid prizes' basically means if you are going to willfully and knowingly do something stupid, illegal, or out of regulations, you need to be prepared to accept the consequences. It's usually used when someone suffers due to a situation entirely of their own making.

I heard this phrase a lot throughout my career as a soldier. ‘Play stupid games, win stupid prizes’ basically means if you are going to willfully and knowingly do something stupid, illegal, or out of regulations, you need to be prepared to accept the consequences. To help clarify, I will include a story about a former soldier of mine.

A junior soldier of mine wanted to purchase a vehicle. It was his first one ever, and he was very eager to get it during the weekend. Myself and my Fire Support Officer briefed him that he should buy from a reputable dealership, and that a license, registration, and insurance were necessary to operate a vehicle… Lawfully anyway. We both told him that we would like to accompany him to the dealership so we could help him make a sensible purchase. The young man listened and stated he would comply with all that was briefed to him. No problems right? Haha.

The next weekend I get a call from my First Sergeant that I needed to meet him in his office regarding my soldier. I comply. When I had got there, I found out that he gotten pulled over on post for speeding and doing an illegal U-Turn away from a Military Police checkpoint. When he was pulled over, he had no license, registration, or insurance. Le sigh. We told him what he needed right?

My First Sergeant got him out of some serious trouble, but I had to counsel the soldier on paper about having the proper documentation to operate a vehicle, as well as have him do corrective training for two weeks. Slap on the wrist, we let him know how potentially bad this could be. Dis Kid get the message right? More to follow.

So a couple of weeks go by, no issues from any of my soldiers. The young man was told he is not to operate his vehicle until he has a proof license, insurance, and registration. That's all he had to do, just show us that he was in the process of securing said documents.

I get a call at night from first Sergeant informing me that I need to see him tomorrow regarding my soldier. Again. He caught the soldier driving and waved him down. He asked the young man himself to see all of his documentation. Lo and behold, the soldier had made no effort to do so. Still driving illegally. The first Sergeant lets him go and told him he was at the mercy of the MPs that evening.

The next morning, I take the soldier into the office and read him his counseling for a Field Grade Article 15. What's that, you may wonder? It is the punishment handed down from a field grade officer that reduces a soldier in rank, pay is halved for two months, and 45 days extra duty. I told him he basically wanted to feel what it was like to get a ticket. So now he knew. He got in trouble for some other things that I subsequently found out about that I will not mention. However, this young man was told how to do something, what he needed to have, and who to talk to regarding the situation above. He got in trouble once and was given a warning and instructions on how to not make the same mistake again. The Young man decides to be hard-headed, gets in trouble yet again by the same individual who saved his skin the first time. As he did not heed directions and warnings, he suffered the consequences, big time.

Does the phrase "If you play stupid games, you win stupid prizes" ring true for you in your life?

Sure does.

I love that phrase, actually! A cut above “Ask a stupid question, get a stupid answer” on the true-use-cliche scale.

Yeah, I don’t mind stupid prizes. I’m always pretty ****ing clear, though: it’s a game when and if both know they’re playing, and same rules apply to each side. I am not the sort of person to say “I don’t play games.” I play many and sometimes well, but I don’t play games where it’s not a game. Or where only one person thinks it’s a game. Long as both are playing, though? Hey! Fun city, next ten exits. Some games you just make up with someone, adding rules as you go, playing along impromptu. Some of those games, it’s pretty clear from the jab and rib and rolling of eyes from both sides, are stupid.

And sometimes it’s not even clear why you started, or why you continue. Except the other one’s caught the spirit (somehow) and is in it to win it, and they must know something you don’t, so you go on. Or you feel you’ve just attained the edge, so you go on. Or maybe both of you are proceeding ’cause you want to see what the stupid prize is.