HungryLion
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I don't know when the first offer was mad, in terms of this contract negotiation but I do remember back in 2018, the team did try to get him more money. they wanted to extend him. That is what lead to the firing of Guerriero and the hiring of Todd France and CAA.
Dak wasn’t eligible for an extension until after the 2018-2019 season. So the soonest he could sign one was in the spring of 2019.
I would imagine it was possible to negotiate before then. But not to actually come to an agreement.