Player wins: 5 of 17 times (29.4%)
2012: Cincinnati Bengals trade Carson Palmer to Oakland Raiders for picks (Dre Kirkpatrick, Giovanni Bernard)
2015: New Orleans Saints trade Jimmy Graham to Seattle Seahawks for pick (Stephone Anthony)
2018: Oakland Raiders trade Amari Cooper to Dallas Cowboys for pick (Johnathan Abram)
2018: Oakland Raiders trade Khalil Mack to Chicago Bears for picks (Josh Jacobs and Damon Arnette)
2019: Seattle Seahawks trade Frank Clark to Kansas City Chiefs for picks (L.J. Collier and Damien Lewis)
Tied for the most likely outcome on this list is that the person getting the play actually “wins” the trade.
Now, I should also say that usually, this involves paying the player in question, but in an era where the salary cap has risen every year (that there wasn’t a pandemic), I think it is more important to look at how much those deals have affected the teams that made them.
I don’t think money has been a problem in most of these cases and in the case that it might be (Frank Clark) the rewards outweigh those problems.