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If you would make the deal as the GM of the other team, then make the deal. That's always been my rule of thumb.
That said, I think you'd have to eat somebody else's crappy contract in return before it would pass that test... I wouldn't likely take on 7 years and $80m in salary for a player having the worst year of their career... at least not without unloading a similar amount of bad money of my own.
But historically speaking, the Jays managed to unload over $80m worth of Vernon Wells... so anything is possible.
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