Win-win is everywhere. What's rare is win-win for everyone
Economists split it in two:
Pareto improvement: someone gains, nobody loses. Truly rare at big scale.
Kaldor-Hicks efficiency: winners gain more than losers lose, so winners could compensate them. Most trade deals, new tech and reforms live here
The catch is the word could π
Compensation rarely happens. The US Trade Adjustment Assistance program, built exactly for workers hurt by trade, stayed small and underused. So the deal was positive sum, the payout wasn't shared.
But at the two-party level, win-win is the default. Every voluntary purchase is one: you value the thing more than the money, the seller values the money more than the thing.
Losers usually appear outside the deal, as third parties (pollution, the closed factory town).