I always thought grant liked to claim he had some magic analytic that would predict NBA success and they tried to out presti everyone. But they screwed it up
Chris Grant deserves to be mentioned in the same vein as some of the worst GMs to ever grace Cleveland sports. Sure, he provided us many "assets", but many of those were acquired thanks to Dan Gilbert opening up his check book to take on shitty contracts for picks. Grant lucked into #1 picks in 3 of 4 years. That's simply amazing, especially given that two of those had such a low chance of hitting.
There's really no debating the Kyrie and Wiggins pick, at the time or even now. Although Grant wasn't here to draft Wiggins, I'm going to go out on a limb and give him the benefit of the doubt (although I shouldn't) that he wouldn't have passed on him. Kyrie and Wiggins were slam dunks whether your the GM of an NBA franchise or a casual fan with a hot take. I know someone is going to bring up Jabari Parker, but I wasn't buying the hype of him over Wiggins then, and I'm not buying it now. Wiggins was the superior talent then, now, and liekly forever. Embiid isn't being included due to his injury being discovered pre-draft.
Now, the other picks...
2011: I like TT, and it's hard to be overly critical of the pick especially considering the other possibility would've likely been Jonas V, but man do Klay or Kawhi sound good in hindsight. Or, Brandon Knight even... but Grant just refused to pick BPA, regardless of position, and allow the coaching staff to figure it out. Which was a trend in '12 and '13 drafts also.
2012: Dion Waiters at 4 despite the organization doing zero homework on him. Taking him above Lilliard and Drummond, who I think we can all agree would be amazing to have right now, and would've likely helped us win a ring last year or at least be in a better position to win one this year. He also took Waiters over Barnes, which may not have been completely awful given that Griffin cleaned up Grant's mess by trading Waiters for JR/Shump, but Barnes would have filled a glaring need at that time. Not to mention this team desperately needs a young SF whether it's today with LeBron or 3 years ago without LeBron.
He also traded 3 picks to move up a few spots to draft Tyler Zeller. He's a solid player with a limited ceiling, but the price is silly given the return. Two of those picks, 33 and 34, were one spot ahead of Draymond Green. Pick 34 is where RCF darling Jae Crowder went.
2013: Already mentioned Anthony Bennett... who's best contribution was matching contracts to trade for Kevin Love. He literally could've picked almost anyone in that draft and it would have been a better pick. Sergey Karasev at 19. We were all kind of high on him at the time so won't kill him too much for that pick, but man does Gorgui Deng look good 2 spots later, or Rudy Gobert at the end of round 1. Who are also guys I remember being highly touted on this board, and who would have been very impactful on our current roster.
Other moves Grant made that are hurting us now....
1) Jarrett Jack signing
2) Luol Deng trade
3) Spencer Hawes trade
Jack's contract was so bad the Cavs had to give up a 2016 1st rounder and Zeller just to move him. Which, despite the financial impact, it's too bad because Jack could've helped as a backup PG last year... especially after Kyrie went down and Delly was ran into the ground.
Cavs gave up 1 first rounder and 4 second rounders for Deng and Hawes rentals to chase a 8 seed. A fucking 8 seed... that almost cost us Wiggins (Love). Granted, that 1st has still yet to be conveyed because the Kings are consistently awful, but they are still assets that could've been used to facilitate deals today when the cupboard is now bare.
If anyone has anything else to add to this depressing chain of events, please share. I didn't include Bynum, because it was a low risk signing at the time, and for a team like the 2013 Cavs he was worth swinging for the fences on. We really got bailed out by LeBron coming back, and we're a contender in spite of everything above because of it... but man does it still hurt thinking what this team could be today, or even tomorrow, had Grant not been so incompetent.