Buy-Win

When a professional equity options trader is forced to buy back a short stock position (called a Buy-In) that hedges a long delta options position and the stock opens higher the next day.

You go out short 10000 shares of EET against a long 10000 delta options position. Overnight you are forced to buy back your shares at $40. The next day the stock opens at $42. You have just made $20000, hence the term Buy-Win.

Buy The Win

A rally bet against your team, to ensure the win by playing your luck.
Your soul may be crushed by a 3 game comeback, from having a 3 game lead, in a 7 game series. So in game 7 you place a bet against your team.

A. Your team wins. YAY
B. You win money. (use this money to drown your sorrows)

I'm gonna be sweating the Canucks vs Blackhawks so hard tonight, I'm gonna Buy the win.

Buy-winning

The act of spending money at a great loss to the consumer, but still a tremendous win for both the seller and the buyer.

Interviewer- "Charlie i heard you were wasting a lot of your money at a clothes store this weekend. Is it true you bought a bowling shirt for 800 dollars?"
Charlie- "Yes, but i like my shirt so i would say i wasn't wasting my money but i was buy-winning."