Small history here for me. I've become fan of the Celtics in I believe november 2014.
And the first time I looked into college prospects for the draft was in 2016.
I'm not going to adress the very late first rounders, because mostly it's indifferent.
Hated the pick, and I was right
2016(16) Guerschon Yabusele
Honestly, I had no idea who this guy was when we drafted him. Seemed like a big reach, where a draft-and-stash-strategy was prioritized over taking BPA. Yabusele was a wasted pick and with his dead salary he's still hurting us a bit.
2016(45) Demetrius Jackson
When I saw Jackson play in summer league I thought he had a future with the Celtics. However this pick is kind of important, because based on my mock draft we'd have picked Fred VanVleet here instead.
2019(14) Romeo Langford
This is a pick I hated last year. In fact I disliked what we did in that draft all together. I have to admit that the players I wanted at the respective spots (Nassir Little, Dylan Windler, Bruno Fernando) haven't panned out either. While concerns about his shooting are very real I do have some faith in him now. However in a re-draft he'd go lower than 14 and not that NBA2K-ratings are without debate, but there noone of our draftees from the 2019 draft class make it into the first round.
Hated the pick, and I was wrong
2016(3) Jaylen Brown
Had no experience in looking into college prospects, therefore I mainly relied on statistics and Brown wasn't near a lottery pick based on that, so I really didn't understand this pick. Boy was I wrong. I fell for the Dragan Bender hype. Unfortunately Bender was a total bust. They might have removed me from that executive position immediately
2017(3) Jayson Tatum
Well hate is a big word here. I was baffled that we traded the nr 1 pick for nr 3, because I believed Markelle Fultz was deservedly seen as the best talent available. In hindsight it was a great pick, but the trade itself only delivered 2019(14)=Langford, so ultimately it wasn't a big heist. For that 3rd pick I had Jonathan Isaac just ahead of D'Aaron Fox.
2019(22) Grant Williams
Not really sure in which category to put Grant Williams. I had Grant at 23 on my board so I didn't think it was a bad pick, nonetheless I had other guys (Little, Windler, Fernando, Bazley and Gafford) ahead of him who where still available. Also I think Celtics fans are much higher on Grant than other NBA fans. Jury is still out on Grant Williams.
Loved the pick, and I was right
2017(37) Semi Ojeleye
I liked Semi Ojeyele and considering that there wasn't much talent available at that point I think it was still a good pick. We have to move on from Ojeleye, but you can't expect much from a second round pick anyway.
2018(27) Robert Williams
This draft was a dream scenario. The Celtics needed a center and all the teams kept on drafting guards and wings, while two lottery talent bigs were left on the board. I preferred Mitchell Robinson, but I was happy with Robert Williams as well. I'm still convinced that Williams should be developed into our future starting center.
Loved the pick, and I was wrong
2016(23) Ante Zizic
Again, this was the first time I made a mock draft for myself. I had Zizic as 4th on my board, so based on that we would have drafted him with the 16th pick in that draft. Anyway, though he's still in the league there were some good players drafted just after him (27 Siakam, 29 Dejounte Murray, 32 Zubac - who was also high on my board), so it was a bad pick in the end.
2019(34) Carsen Edwards
As I said previously I didn't like our draft last summer, but I was hopeful that Edwards could be the exception to that.
After an impressive campaign in the summer league and pre-season he has played awful and unfortunately I don't see a future for him in the NBA.Comparison overall
To make a comparison between whom have been drafted and what I would have done I assume we'd made the same trades as happened in reality (like Zizic to Cavs, 2016 - 31 and 35 for future pick, 2017 - Philly trade, 2019 - draft trades).
From all the drafted players since 2016: Jaylen Brown, Jayson Tatum, Semi Ojeleye, Robert Williams, Romeo Langford, Grant Williams, Carsen Edwards and Tremont Waters are still on the roster/under control by the Celtics.
Danny Ainge made some genius trades, which I wouldn't have made, but just based on the same made draft picks I would have assembled a very different roster anyway. Assuming the same developments as in real life the following group would be under contract: Fred VanVleet, Jonathan Isaac, Mitchell Robinson, Nassir Little, Dylan Windler, Bruno Fernando (and Tremont Waters?).
I doubt anybody would switch Tatum + Brown + R.Williams + G.Williams + Langford + Edwards => Isaac + VanVleet + Robinson + Little + Fernando + Windler