I know Trout is worth far more than his contract, but no player of this caliber, at this age, has ever been moved with this much money owed to them either. Obviously he's worth every penny, but teams still need to find a way to shoehorn in a $33 million a year contract for three years. In taking on Trout, some teams would maybe have to facilitate a secondary trade or a salary dump, which I'm sure they'd be happy to do, but Trout's contract can still be a boon for some teams and I imagine would be a bargaining point in negotiations to not give up as much talent in return. And I think if we look at any trade to compare this to, I'd suspect the Johan Santana deal is the closest. It was trade that had the contingency of him getting a contract extension, and he was arguably the best pitcher in the majors at the time. Trout's contract is 6 years $144 million. Presently he is owed $134 million over 5 years. The contract extension Santana signed was 6 years $137 million. He was entering his age 29 season at the time so the ages don't match up, but he was arguably the #1 pitcher in baseball who had just come off a 5 year run of ownership over the American League. The return for Johan Santana was a then slap hitting Juan Pierre clone in Carlos Gomez, Deolis Guerra, Philip Humber and Kevin Mulvey. That's... not great.