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CHCNYY⇄CHCEach player is valued on what he was expected to produce at the time of the trade, versus what he actually produced for his new team.
Expected WAR blends a player's pedigree (composite top-100 rank / draft slot, or a baseline) with his recent track record, projected over the years of team control acquired. The ± figure is a historically calibrated predictive standard deviation, measuring how widely comparable forecasts have missed around their expected value. Surplus values that production at the FA market price of a win (~$8M/WAR) minus salary — so cost-controlled players carry large surplus and expensive ones little, even at the same WAR. Who won is descriptive, not a skill claim: ~99% of a trade's outcome is unforeseeable at the time.