Two Bad Drafts: 2016 and 2019

[Roy H.]

I think that when people criticize Danny Ainge's latter years here, a lot of the criticism stems from the team's decisions in the 2016 and 2019 drafts.  Yes, the biggest "what if" is passing on Giannis after scouting him, but that was one missed pick on a superstar that caught the league by surprise.  The 2016 and 2019 drafts were different, in that the selections were shaped by financial / roster decisions.

As a refresher, here were our picks:

2016:

#3 - Jaylen Brown (obviously a home run)
#16 - Guerschon Yabusele
#23 - Ante Zizic
#31 and #35 - traded to Memphis for 2019 LAC #1
#45 - Demetrius Jackson
#51 - Ben Bentil

2019:

#14 - Romeo Langford
#20 - traded to Philly for #24 (traded to dump Baynes' salary) and #33 (Carsen Edwards)
#22 - Grant Williams
#51 - Tremont Waters

Now, even acknowledging that mid- to late first rounders are a crap shoot, that's a pretty significant lack of success.  So, what was the problem?  And was it inevitable?

In 2016, our draft decisions were informed by roster slots.  We went into the draft with the philosophy of either stashing picks, or trading them for value.  We went into the draft with six picks, and only ended up utilizing two 2017 roster spots on them:  Jaylen Brown and Demetrius Jackson.

Our 2017 roster ended up being:

Bradley
Brown
Crowder
Green
Horford
Jackson
Jerebko
A. Johnson
Mickey
Olynyk
Rozier
Smart
Thomas
Young
Zeller

As most of us probably remember, Jackson, Young and Mickey were complete dead weight.  It seems completely counter-productive to pass on draft picks because of roster spots, and then utilize 20% of the roster on guys who couldn't produce at the NBA level. 

Perhaps most difficult to understand is, what were we thinking giving a roster spot to Jackson?  Full disclosure:  I like the guy a lot.  I thought he'd be an NBA player.  But, if anybody is going to be stashed overseas or in the G-League, why not him?  That would have allowed us to use the #16 on a better pick.  And who was out there at the time?  Malik Beasley, Caris Lavert, Pascal Siakim, Malcolm Brogdon and the guy that I think many of us wanted Ainge to draft:  Dejounte Murray.  Murray was forecast as a borderline lottery pick, and somehow almost fell out of the first round.  We could have taken him at #16 or #23, but were hyper-focused on not using a roster spot.  Instead, we gave that spot to a vastly inferior player in Jackson.  That's just bad decision making, several times over.

2019 was another situation where we didn't take the best player available when it was our turn, but there was another seeming mistake:  not trading up to secure our guy.  This was the draft where Danny pounded the table when Tyler Herro was taken one spot ahead of us.  You have to wonder:  did Danny pick up the phone and offer the #20 and/or the #22 to move up to #13?  Yes, #14 + #20 for #13 isn't necessarily a good trade value-wise, but was it on the table?  Sometimes, when you really like a guy, you need to pay the price to get him.

One has to wonder:  did we not trade up because our focus was on clearing max cap space?  As we all know, we traded out of the #20 spot, essentially for a salary dump of Baynes and Carsen Edwards.  Available at #20:  Matisse Tybulle and our purported target, Brandon Clarke.  Did Ainge get greedy here?  Wouldn't it have made sense to take the player we wanted at #20, and then figured out another way to clear cap space?  We already knew that Horford and Kyrie were gone at that point (despite it being during the tampering period).  Could we have tried to do a sign and trade, either keeping Baynes or sending him elsewhere?  If not, shouldn't we have taken our target at #20, and moved the #22 in the salary dump?  Yes, we picked up the #33 pick, but the second round that year was very weak.

Obviously, any team's draft can be nitpicked, particularly in hindsight.  But, to me, these two drafts are good examples of what not to do on draft night.  You can't go into it with the plan of using your picks to "stash" players, or to make salary dumps.  (Danny arguably combined both of these issues in the 2021 draft, getting poor value for the #30 pick to save money and because we didn't want to add another rookie).  If one of these picks had gone the right way -- particularly in that 2016 draft -- we might already be talking about having the coveted "third star" on the roster.  Instead, we keep using picks to buy our way out of past mistakes, which long-term can be crippling to a franchise.

[Walker Wiggle]

I think that when people criticize Danny Ainge's latter years here, a lot of the criticism stems from the team's decisions in the 2016 and 2019 drafts.  Yes, the biggest "what if" is passing on Giannis after scouting him, but that was one missed pick on a superstar that caught the league by surprise.  The 2016 and 2019 drafts were different, in that the selections were shaped by financial / roster decisions.

As a refresher, here were our picks:

2016:

#3 - Jaylen Brown (obviously a home run)
#16 - Guerschon Yabusele
#23 - Ante Zizic
#31 and #35 - traded to Memphis for 2019 LAC #1
#45 - Demetrius Jackson
#51 - Ben Bentil

2019:

#14 - Romeo Langford
#20 - traded to Philly for #24 (traded to dump Baynes' salary) and #33 (Carsen Edwards)
#22 - Grant Williams
#51 - Tremont Waters

Now, even acknowledging that mid- to late first rounders are a crap shoot, that's a pretty significant lack of success.  So, what was the problem?  And was it inevitable?

In 2016, our draft decisions were informed by roster slots.  We went into the draft with the philosophy of either stashing picks, or trading them for value.  We went into the draft with six picks, and only ended up utilizing two 2017 roster spots on them:  Jaylen Brown and Demetrius Jackson.

Our 2017 roster ended up being:

Bradley
Brown
Crowder
Green
Horford
Jackson
Jerebko
A. Johnson
Mickey
Olynyk
Rozier
Smart
Thomas
Young
Zeller

As most of us probably remember, Jackson, Young and Mickey were complete dead weight.  It seems completely counter-productive to pass on draft picks because of roster spots, and then utilize 20% of the roster on guys who couldn't produce at the NBA level. 

Perhaps most difficult to understand is, what were we thinking giving a roster spot to Jackson?  Full disclosure:  I like the guy a lot.  I thought he'd be an NBA player.  But, if anybody is going to be stashed overseas or in the G-League, why not him?  That would have allowed us to use the #16 on a better pick.  And who was out there at the time?  Malik Beasley, Caris Lavert, Pascal Siakim, Malcolm Brogdon and the guy that I think many of us wanted Ainge to draft:  Dejounte Murray.  Murray was forecast as a borderline lottery pick, and somehow almost fell out of the first round.  We could have taken him at #16 or #23, but were hyper-focused on not using a roster spot.  Instead, we gave that spot to a vastly inferior player in Jackson.  That's just bad decision making, several times over.

2019 was another situation where we didn't take the best player available when it was our turn, but there was another seeming mistake:  not trading up to secure our guy.  This was the draft where Danny pounded the table when Tyler Herro was taken one spot ahead of us.  You have to wonder:  did Danny pick up the phone and offer the #20 and/or the #22 to move up to #13?  Yes, #14 + #20 for #13 isn't necessarily a good trade value-wise, but was it on the table?  Sometimes, when you really like a guy, you need to pay the price to get him.

One has to wonder:  did we not trade up because our focus was on clearing max cap space?  As we all know, we traded out of the #20 spot, essentially for a salary dump of Baynes and Carsen Edwards.  Available at #20:  Matisse Tybulle and our purported target, Brandon Clarke.  Did Ainge get greedy here?  Wouldn't it have made sense to take the player we wanted at #20, and then figured out another way to clear cap space?  We already knew that Horford and Kyrie were gone at that point (despite it being during the tampering period).  Could we have tried to do a sign and trade, either keeping Baynes or sending him elsewhere?  If not, shouldn't we have taken our target at #20, and moved the #22 in the salary dump?  Yes, we picked up the #33 pick, but the second round that year was very weak.

Obviously, any team's draft can be nitpicked, particularly in hindsight.  But, to me, these two drafts are good examples of what not to do on draft night.  You can't go into it with the plan of using your picks to "stash" players, or to make salary dumps.  (Danny arguably combined both of these issues in the 2021 draft, getting poor value for the #30 pick to save money and because we didn't want to add another rookie).  If one of these picks had gone the right way -- particularly in that 2016 draft -- we might already be talking about having the coveted "third star" on the roster.  Instead, we keep using picks to buy our way out of past mistakes, which long-term can be crippling to a franchise.

I appreciate this post and don’t necessarily disagree with the OP here, but in general I think we spend way too much time nitpicking who was chosen in the draft in the area of 20-60. You’re not supposed to hit on players in this range; when you do, it’s gravy. Ainge has had plenty of misses beyond those two drafts in that range. He’s also had some real gems. (A guy named Rondo comes to mind, for instance.)

The OP himself acknowledges the “home run” of Jaylen at #3. Most of us on wanted Kris Dunn, but Ainge went with the raw kid with the shaky jump shot. A couple years later he’s scoring 25 ppg and looks like a multi time al star. Those are the picks that make or break a franchise, not the ones at the back end of the draft, and Ainge’s track record with those picks is solid.

[bdm860]

Weren't the actions going into the 2016 draft based on having room for 2 max free agents (Durant and Horford)?  If so, I think that's a risk worth taking (not taking on salary, and keeping roster spots open).  Demetrius Jackson was only signed well into free agency, and for less money than the #16 pick, but not sure if that influenced things or not.  Also if we get Durant/Horford, maybe the C's need the roster spots to sign ring chasing vets?  I dunno, just spitballing.

[nebist]

Great, fair analysis of some breakdowns in the process of decision-making in those two drafts. Those drafts are indicative of a critique of Danny in his later years on the job. It seemed like he got too cute at times, and he was always trying to wait for deadlines or sweetheart deals to extract the utmost value of his assets. That can work, but it can also blow up in your face as it did in these instances. Other teams called our bluff; we were stuck with too many picks and not enough roster spots, and we made bad decisions. Even though it wasn't a home-run move, Brad's "early" Kemba/Horford trade provided clarity leading into the rest of the offseason. I like that Brad has been willing to make moves that advance a logical step forward in roster building even if the "value" isn't perfect. There can be a downside to waiting just as real as the potential upside.

[Moranis]

The big what if in 2016 for me was what if Ainge would have made the trade with the Sixers.

It was widely reported that the Sixers offered Covington, Noel, 24, and 26 for 3.  The Sixers were going to take Dunn at 3. 

So that would have left Boston with 16, 23, 24, and 26.  Would that have been enough to move back up to 8?  Remember Sacramento traded 8 for 13, 28, a future 2nd (ended up being #35 Tillman in 2020), and Bogdan Bogdanovic.  They took Papagiannis at 13 and Labissere at 28.  I suspect Sacramento would have still been able to get Papagiannis at 16 and certainly could have still landed Labissere with one of the other picks in the 20's, so would the extra 1st rounder (or maybe 2) made up for Bogdanovic.  Quite possibly.

And why would Boston want to get that 8th pick, because there would have been a pretty decent chance that Jaylen Brown would still be there at 8 (Denver at 7 is really the only other logical landing point).  Now maybe if that is the case, Sacramento doesn't make the trade (because they want Brown) and or maybe Brown isn't there (going to Denver at 7), but it would be possible and even if not, maybe Boston takes whomever in the top 8 fell or takes someone like Poeltl or Sabonis. 

The other side of that trade is that the more established players in Covington and Noel could have also convinced Durant that Boston was a real contender (along with Horford) and maybe he comes to Boston rather than taking the easy path in Golden State.  So the team would have basically started IT, Bradley, Durant, Horford, and Noel with Rozier, Smart, Crowder, Covington, Olynyk, Johnson, and Jerekbo in the rotation without accounting for any of the draft picks.  That is a real title threat, and I don't think that is necessarily the case with the unknown Brown as opposed to Noel/Covington

[td450]

I can live with 2016.

Ainge had two super critical drafts in a row where he had the team well positioned, but he just couldn't accept that he had to start to aggressively overpay, because of the stage the team was at.

The 2019 draft was the biggest fail. I know Tyler Herro had his moment against us in the playoffs, but over the long term the better guy to get was PJ Washington one pick earlier at 12, who would have been a very nice starting PF for a very long time. Brandon Clarke would have been a much more valuable rotation player than Grant Williams, and still may become a starting grade player.

The 2020 draft was notable for failing to get Ty Halliburton.

[Roy H.]

The 2020 draft was notable for failing to get Ty Halliburton.

Can we blame Ainge for that one?

[nebist]

The 2020 draft was notable for failing to get Ty Halliburton.

Can we blame Ainge for that one?

Unclear. Depends on how hard Ainge was banging the phones to move up. In a vacuum, one would think 14+26 could get you to 11, but you need two to tango. If I remember correctly, there wasn't a trade down made in that range, so it's possible Ainge offered a move up deal and was turned down. But, he certainly should have been looking to package 14+26 at least as soon as Haliburton fell past say 8.

[KG Living Legend]

I think that when people criticize Danny Ainge's latter years here, a lot of the criticism stems from the team's decisions in the 2016 and 2019 drafts.  Yes, the biggest "what if" is passing on Giannis after scouting him, but that was one missed pick on a superstar that caught the league by surprise.  The 2016 and 2019 drafts were different, in that the selections were shaped by financial / roster decisions.

As a refresher, here were our picks:

2016:

#3 - Jaylen Brown (obviously a home run)
#16 - Guerschon Yabusele
#23 - Ante Zizic
#31 and #35 - traded to Memphis for 2019 LAC #1
#45 - Demetrius Jackson
#51 - Ben Bentil

2019:

#14 - Romeo Langford
#20 - traded to Philly for #24 (traded to dump Baynes' salary) and #33 (Carsen Edwards)
#22 - Grant Williams
#51 - Tremont Waters

Now, even acknowledging that mid- to late first rounders are a crap shoot, that's a pretty significant lack of success.  So, what was the problem?  And was it inevitable?

In 2016, our draft decisions were informed by roster slots.  We went into the draft with the philosophy of either stashing picks, or trading them for value.  We went into the draft with six picks, and only ended up utilizing two 2017 roster spots on them:  Jaylen Brown and Demetrius Jackson.

Our 2017 roster ended up being:

Bradley
Brown
Crowder
Green
Horford
Jackson
Jerebko
A. Johnson
Mickey
Olynyk
Rozier
Smart
Thomas
Young
Zeller

As most of us probably remember, Jackson, Young and Mickey were complete dead weight.  It seems completely counter-productive to pass on draft picks because of roster spots, and then utilize 20% of the roster on guys who couldn't produce at the NBA level. 

Perhaps most difficult to understand is, what were we thinking giving a roster spot to Jackson?  Full disclosure:  I like the guy a lot.  I thought he'd be an NBA player.  But, if anybody is going to be stashed overseas or in the G-League, why not him?  That would have allowed us to use the #16 on a better pick.  And who was out there at the time?  Malik Beasley, Caris Lavert, Pascal Siakim, Malcolm Brogdon and the guy that I think many of us wanted Ainge to draft:  Dejounte Murray.  Murray was forecast as a borderline lottery pick, and somehow almost fell out of the first round.  We could have taken him at #16 or #23, but were hyper-focused on not using a roster spot.  Instead, we gave that spot to a vastly inferior player in Jackson.  That's just bad decision making, several times over.

2019 was another situation where we didn't take the best player available when it was our turn, but there was another seeming mistake:  not trading up to secure our guy.  This was the draft where Danny pounded the table when Tyler Herro was taken one spot ahead of us.  You have to wonder:  did Danny pick up the phone and offer the #20 and/or the #22 to move up to #13?  Yes, #14 + #20 for #13 isn't necessarily a good trade value-wise, but was it on the table?  Sometimes, when you really like a guy, you need to pay the price to get him.

One has to wonder:  did we not trade up because our focus was on clearing max cap space?  As we all know, we traded out of the #20 spot, essentially for a salary dump of Baynes and Carsen Edwards.  Available at #20:  Matisse Tybulle and our purported target, Brandon Clarke.  Did Ainge get greedy here?  Wouldn't it have made sense to take the player we wanted at #20, and then figured out another way to clear cap space?  We already knew that Horford and Kyrie were gone at that point (despite it being during the tampering period).  Could we have tried to do a sign and trade, either keeping Baynes or sending him elsewhere?  If not, shouldn't we have taken our target at #20, and moved the #22 in the salary dump?  Yes, we picked up the #33 pick, but the second round that year was very weak.

Obviously, any team's draft can be nitpicked, particularly in hindsight.  But, to me, these two drafts are good examples of what not to do on draft night.  You can't go into it with the plan of using your picks to "stash" players, or to make salary dumps.  (Danny arguably combined both of these issues in the 2021 draft, getting poor value for the #30 pick to save money and because we didn't want to add another rookie).  If one of these picks had gone the right way -- particularly in that 2016 draft -- we might already be talking about having the coveted "third star" on the roster.  Instead, we keep using picks to buy our way out of past mistakes, which long-term can be crippling to a franchise.

I appreciate this post and don’t necessarily disagree with the OP here, but in general I think we spend way too much time nitpicking who was chosen in the draft in the area of 20-60. You’re not supposed to hit on players in this range; when you do, it’s gravy. Ainge has had plenty of misses beyond those two drafts in that range. He’s also had some real gems. (A guy named Rondo comes to mind, for instance.)

The OP himself acknowledges the “home run” of Jaylen at #3. Most of us on wanted Kris Dunn, but Ainge went with the raw kid with the shaky jump shot. A couple years later he’s scoring 25 ppg and looks like a multi time al star. Those are the picks that make or break a franchise, not the ones at the back end of the draft, and Ainge’s track record with those picks is solid.

 "Your not supposed to hit on those picks"

Ahhh. Yes you are. That's why my philosophy is you swing for the absolute fences no matter where you draft.

 ESPECIALLY in the middle of the first round when players like Giannis, Kawhi, Michael porter Jr, Siakim, even guys like Murray and  Levert are taken.

[mobilija]

The big what if in 2016 for me was what if Ainge would have made the trade with the Sixers.

It was widely reported that the Sixers offered Covington, Noel, 24, and 26 for 3.  The Sixers were going to take Dunn at 3. 

So that would have left Boston with 16, 23, 24, and 26.  Would that have been enough to move back up to 8?  Remember Sacramento traded 8 for 13, 28, a future 2nd (ended up being #35 Tillman in 2020), and Bogdan Bogdanovic.  They took Papagiannis at 13 and Labissere at 28.  I suspect Sacramento would have still been able to get Papagiannis at 16 and certainly could have still landed Labissere with one of the other picks in the 20's, so would the extra 1st rounder (or maybe 2) made up for Bogdanovic.  Quite possibly.

And why would Boston want to get that 8th pick, because there would have been a pretty decent chance that Jaylen Brown would still be there at 8 (Denver at 7 is really the only other logical landing point).  Now maybe if that is the case, Sacramento doesn't make the trade (because they want Brown) and or maybe Brown isn't there (going to Denver at 7), but it would be possible and even if not, maybe Boston takes whomever in the top 8 fell or takes someone like Poeltl or Sabonis. 

The other side of that trade is that the more established players in Covington and Noel could have also convinced Durant that Boston was a real contender (along with Horford) and maybe he comes to Boston rather than taking the easy path in Golden State.  So the team would have basically started IT, Bradley, Durant, Horford, and Noel with Rozier, Smart, Crowder, Covington, Olynyk, Johnson, and Jerekbo in the rotation without accounting for any of the draft picks.  That is a real title threat, and I don't think that is necessarily the case with the unknown Brown as opposed to Noel/Covington

You are clearly a very knowledgeable basketball mind and I enjoy your knowledge of history but it's posts like these that drive me away from your opinion...

Often it's an argument but this time just a critique, but your post is filled with so many ifs and maybes that it's hard to take seriously. This critique of Ainge you present is just a mazy rabbit hole... all one can do is shrug their shoulders and say "maybe?"

[ETNCeltics]

IMO, hard to criticize Ainge for 2016. He got JB, which makes it one of the most productive drafts in franchise history. Ainge was building and saving space for that team towards signing a big time FA, and by 2018, he put one of the NBA's deepest and most talented teams on the floor. It fell apart opening night when Hayward's leg broke, but it's hard to fault what he did up to that point. I believe I read a few months ago that the Celtics' rotation from that year, has signed almost a billion $$ in contracts since, unfortunately, only 3 of those guys signing with us.

Re: 2019, Herro's a long way from being a star, and Brandon Clarke is an end of the rotation player. He couldn't get on the floor in the playoffs. Either way, we may have a 3rd star on the roster already. It was undeniably a bad draft for us, but looking at what was there and what has transpired since, there was never that much there to begin with.

I believe we're very close to being a contender now, may very well be one before the season is over. What we're missing as much as talent is chemistry. Hopefully we see that developing in the coming months.

[Roy H.]

IMO, hard to criticize Ainge for 2016. He got JB, which makes it one of the most productive drafts in franchise history. Ainge was building and saving space for that team towards signing a big time FA, and by 2018, he put one of the NBA's deepest and most talented teams on the floor. It fell apart opening night when Hayward's leg broke, but it's hard to fault what he did up to that point. I believe I read a few months ago that the Celtics' rotation from that year, has signed almost a billion $$ in contracts since, unfortunately, only 3 of those guys signing with us.

I think you can criticize.  We had four picks between #16 and #35.  Hitting on high lottery picks is quite important, but so is filling in the roster with deeper picks.  Taken in that range there were several good players that really could have helped:  Brogdon, Siakim, LeVert, Beasley, Zubac, Murray.  This isn't a case of saying "there was one diamond, and you missed".  We had four bites at the apple, and ended up with nothing to show for it (except for Jackson's and Yabu's salary, each of which are still eating up cap space for us).

[td450]

Regardless of how you feel about a particular guy, to me Ainge failed post Kyrie to be aggressive enough to get the last couple of pieces he needed.

I would have been OK if he had taken a shot in 2019 or 2020 and the player he got didn't pan out as worth overpaying for. But he seemed to not understand where he was. He had to overpay, and he didn't do it.

As a strategy, the draft is a better place to take your risks, even if you only hit it every 2nd or 3rd guy.

[nickagneta]

To me, the book is still out on 2019 and we need to let it play out some more after the Covid nuttiness that has been the 1st couple years of those players' careers.

Regarding 2016, can any draft be considered bad if you land a soon to be multi time All-Star and All-NBA player, because that is what Brown will be?

[Roy H.]

To me, the book is still out on 2019 and we need to let it play out some more after the Covid nuttiness that has been the 1st couple years of those players' careers.

Regarding 2016, can any draft be considered bad if you land a soon to be multi time All-Star and All-NBA player, because that is what Brown will be?

Regarding 2019, we’re talking Romeo, Williams and Edwards.  Edwards is already gone, and I’ll be surprised if Williams gets his option picked up.  Romeo, at best, has shown nothing due to injuries, which were a knock on him when he was drafted.  Even if Romeo pans out, trading down and missing on good players while doing so is an issue.

And, I think when a team has five picks in the top 35, they’re open to criticism, even if one pick pans out.  Danny squandered assets.