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An excerpt from Java for Dummies, 6th Edition:

Hello, again. You're listening to radio station WWW, and I’m your host, Sam Burd. It's the start again of the big baseball season, and today station WWW brought you live coverage of the Hankees versus Socks game. At this moment, I’m awaiting news of the game’s final score.

If you remember from earlier this afternoon, the Socks looked like they were going to take those Hankees to the cleaners. Then, the Hankees were belting ball after ball, giving the Socks a run for their money. Those Socks! I’m glad I wasn’t in their shoes.

Anyway, as the game went on, the Socks pulled themselves up. Now the Socks are nose to nose with the Hankees. We’ll get the final score in a minute, but first, a few reminders. Stay tuned after this broadcast for the big Jersey’s game. And don’t forget to tune in next week when the Cleveland Gowns play the Bermuda Shorts.

Okay, here’s the final score. Which team has the upper hand? Which team will come out a head? And the winner is... oh, no! It’s a tie!

What do you think come out a head means? Well, to tell you the truth, I think I have an idea of what it means. It probably means that one of the teams is going to win the match, but apart from that what can you say about the expression and its usage itself? How do you think the author came up with this expression?

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    The expression is actually come out ahead, with no space between a and head. And your idea of what it means is correct: come out ahead means to end a game with a better score (or time/position, in the case of a race); in other words, it means "to win." – pyobum Apr 6 '15 at 8:34
  • Another meaning of "to come out ahead" (though it's not the meaning here) is to emerge from a situation in a better position than one was in upon entering it. You can't go wrong with this investment because commercial property values are appreciating so rapidly in this section of town that you're bound to come out ahead, even if the business tanks. You will be able to sell the property for a handsome profit. – Tᴚoɯɐuo Apr 6 '15 at 10:58
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If that is a direct quote, then the book contains a typo. The correct phrase is "come out ahead" - because "ahead" is one word. As written it sounds as if the team will exit the situation transformed into a literal head.

This word is formed from the prefix "a-" meaning "in or at" and "head". Thus "ahead" literally means "at the head" or in this case "in the lead".

As you correctly surmised, the phrase is asking which team will win. When you "come out ahead" you come away from some event in a better situation than you started, or than some other person. You may be coming out ahead of another person or team, or of your past self.

As for how the author came up with it - he didn't. This is an extremely common phrase, though in this case it would appear that the author mistyped it.

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