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I wouldn't do 5/$90mil. At least not until the offseason and most likely not even then. You can trade him and pay him that much in the offseason if you wanted to.
The fact that Bedard has had multiple arm problems make him a guy I'm not willing to pay full value for. He WILL NOT be durable like Randy has been in his career. Hes also 4 months away from FA. Does he want to risk injury again to wait out for his big pay day?
I think $13-14mil over 5 years does it. $14mil over 7 years was his agents OPENING offer for crying out loud and the market has crashed since then.
We have to have to keep perspective too. Bedard is an excellent starter when healthy. But he is definetly NOT Pedro/Randy in their primes.