I think executive of the year gets clouded by regular season results from that year, which has little to do with how well an executive did that year. I think some of the worst teams' leaders could win this award.
Here are my top 3 for this year and why
1.) Sam Hinkie-76ers- trading jrue holiday for nerlens noel and a lotto pick was a very smart move, and if Carter-Williams pans out, along with a likely top 3 pick and multiple ungaranteed 2nd rounders to trade or use at their discretion. Great year for the sixers rebuild.
2.) Masai Ujiri-Raptors- Trading away Rudy Gay for productive players was a huge win for them, and getting rid of the least productive player in NBA history in Andrea Bargnani for a decent haul is just icing on the cake. If he can resign Lowrey in the offseason and trade Demar Derozan for a more efficent and productive player while his value is high, then they are very much looking good.
3.) Danny Ainge- Celtics- we all know what happened here. Getting so many 1st round picks for Doc, KG and Pierce and also some expiring contracts, allowing Rondo to heal up, playing their way to a top 5 pick. Hopefully we can resign Humphries to a cheaper contract, not match any offers for Bradley and let him walk, force Sullinger to stop taking 3's because it makes him horribly inefficient, and pick a great draft pick (Embiid!). Resign Rondo next year to an extension if possible as that is the cheapest way to go. If we could trade for KLove somehow i would be beyond ecstatic.
I think this award should go to who helped their team the most, not who won the most.