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... but I would think that you could extend Jackson, at (say) 2 x $12 or 3 x $12 for the no-arb years and that would be okay with Boras.
I suspect that Dombrowski is not allowing the contact, because afraid that Boras will blow the deal. My guess is, he's hoping to deal Jackson without the hassle of depending on Boras to be reasonable.
And if that's the case, I'd expect Dombrowski to relent shortly.