I think there is a strong argument for Brad as executive of the year.
1. He hired the right coach and stuck by him.
2. He took a team that appeared to some to have missed its window of contention and revitalized it with some trades that did not look like obvious winners (eg, reacquiring Horford).
3. Where latter-years Danny Ainge seemed laser focused on talent acquisition and damage control, Brad has managed to incorporate fit into the equation, without abandoning talent acquisition. Where Danny seemed gunshy about surrendering value in trades, Brad is happy to do so for the player he wants. But Brad's mid-level talent acquisition (Josh Richardson, Dennis Schroder) laid part of the foundation Brad needed to make some of his more fit-based deals (White, Theis).
He'll have revisionist history working against him, as the people who vote on these things will probaly have some collective amnesia around all of the "Boston needs to move Tatum or Brown" talk from 3 months ago. And once that is forgotten, all Brad did was oversee the core that Danny had built: in Smart, Brown, Tatum, Rob, Grant, Pritchard, 6 of the 8 core rotation players were drafted by Danny, including the 2 stars.