Perhaps ...
Cronin tried to trade the 7th pick for OG but the asking price was crazy town. So he made the correct move not in Lillard's timeline ... and which Lillard more recently liked given that Sharpe is a different piece of work.
Cronin tried to bring in another veteran after Grant and that didn't happen ... or tried to trade the 3 that is Scoot + Ant for a difference maker worth that value but the value in return just wasn't high enough and ... may be the correct move but, again, not in Lillard's timeline.
Was there a plan for the go young timeline? Obviously, yes.
Was there a plan for the Lillard timeline? Obviously, yes. [Their names are Nurkic and Grant.]
Which plan was more likely to happen? The one that did. It's not what I wanted, but I understand (given what's been reported and talked about) how it worked out this way. And the non-lottery picks last year and this year are players I like.
Cronin may have wanted the Lillard path, but he pivoted and picked the Scoot/Sharpe path. What's left is trading Nurkic for a more athletic, healthier center and Lillard for maximum return of size that has skills, youth ... plus picks (and filler contracts of 2 years or less).
Cronin didn't pivot, Joe "was retooling" this team from day 1 after Olshey got the boot. Picks and picks and oh hey, look at all these picks over there.
Lillard freaked out last tank, he was told picks were gonna do all kinds of picky pick things to get win now players, not win later players.
Cronin & Billups knew Nurk, Grant & Simons would take the vacation so Blazers could tank the hell out the team. All 3 of those starters have a history of resting for the lottery improvement agenda.
Lillard got mad about tanking, Mark Spears reported Dame told him where the line got crossed. The Blazers were in the playoff hunt. Damian's squad had already battled it out for 4 months of grueling NBA action. Portland was 28-30, more or less .500.
Maybe the Blazers would have been a 1st round exit? A team stuck in mediocrity ... We'll never know. I was rooting for these guys. So were other fans. It's called happy and sad when your team wins and loses.
People want to see Ant in the playoffs, Grant in the playoffs, these guys are really good at basketball.
..am i right?
We know Lillard can go Supernova in post season.
Nurkic had been getting lots of rest, I figured he could do some playoff damage.
Trading Josh Hart cratered the Blazers. With Winslow out and Nassir in la-la land, Josh was the only swiss army knife left on the team.
The win later trade was once again advertised as the predecessor for the big move to get a "superstar"...
... which in mind was always going to be awesome new rookie #1-2-
3-4-5-6-7