Over the years, I have messed around with various ways to evaluate controversial trades as objectively as possible. The best way that I have settled on is the idea of "surplus value." The CliffNotes version of the idea behind Surplus Value is that you compare the theoretical dollar value of all the assets involved with what those assets are actually worth. A "win-win" trade would be one where both teams are receiving more theoretical value than they are giving up...but that doesn't always happen.
For a more detailed description of how these values are calculated, click here.
For an in depth look at the proposed trade between Santa Fe and Washington DC from Season 53, click here.