Yep, he would. He's buried behind a deep, much better, and well establiahed front court than Boston's. Mickey can't hold his jock... shouldn't use the two names in the same sentence. Rozier was a horrible pick. Expect a re- redo on Smart this year with BKN pick... Kris Dunn. That's all DA is comfortable with.
You can talk all you want about their units being better, etc., etc. but deeper they're not.
Portis wouldn't be getting playing time ahead of Sullinger-Olynyk-Johnson-Zeller add to that Lee and that's 5 players ahead of him depth wise, to say nothing of all the players Stevens uses when going small (Crowder/Jerebko) who'd be getting playing time ahead of Portis.
The reality in all of this, you can think what you want of Portis or how much of a stud he is, but he wouldn't be leap frogging any of these guys unless injuries occurred.
The Celtics bigs are much deeper than Chicago's and even then it took injuries for him to get playing time.
In fact, with all the NBA caliber bigs we have, there wouldn't be room for Portis to dress in the first place to get playing time.
What??? Gasol, Gibson, Noah, and Mirotic are not chopped liver. You could argue that we have more "depth" in terms of C to B-level players (C being a mediocre/average rotation guy) but that would be a pretty flawed definition of the term. In the NBA you don't win just because your 7-8-9 guys are a little better than the other team's.
Anyway I never go overboard with the pick-and-choose draft criticism because the truth is a lot of teams miss on these late-round gems. However, I will say that these are the kind of picks that a team has to make to accelerate the rebuild, especially if you're not out-and-out tanking.
Every time you miss out on getting a hidden gem in the draft it can delay your team's rebuild process. Olynyk is a fine player and will have a nice career. However, if we had drafted Giannis we'd have a huge asset on the team right now that teams would actually be willing to deal for as the centerpiece. Olynyk isn't going to be the centerpiece of any deal for a star, let's be honest.
In conclusion, it's not fair to kill Ainge for missing this or that player but they represent missed opportunities nonetheless. No team drafts perfectly but the ones that do hit it big late in the draft reap a huge reward. Golden State getting Draymond in the 2nd round, Chicago getting Butler at the end of the first, Milwaukee/Giannis at 15, Utah/Rudy Gobert at 27, these types of draft steals are like getting a top 5 pick in the draft for free.
When Ainge hit it big with Jefferson at 15, it was a huge chip that made the Garnett deal possible. When he hit it big with Rondo at 21, it gave us the depth to win a title after most of the remaining players had been dealt away. If Ainge is unwilling to play the tank card, at some point he needs to actually draft someone of that caliber to keep on the roster or use as a trade chip.
Anti-tankers say all the time "the draft is a crapshoot" and "there's talent all throughout the draft - look at Paul George." OK, so then the onus is on Ainge to actually draft one of those players with these late picks. Recently, he hasn't.