Robb: The Celtics should stop playing it safe

Once upon a time, Danny Ainge and the Celtics front office were one of the more active teams in the NBA when it comes to wheeling and dealing. Boston set franchise records for trades as recently as the 2014-15 season, the second year of the team’s ‘rebuild’ following the official end of the Big Three era with the Paul Pierce/Kevin Garnett trade in the summer of 2013.

During that NBA calendar year (2014-15), Boston was in pure draft asset accumulation mode, taking on unwanted contracts for draft capital, selling off their best veterans (Rajon Rondo, Jeff Green) for meaningful returns and buying low on intriguing talent (Isaiah Thomas). All in all, Boston made 11 trades in 12 months, including seven during the regular season itself.

That season was a masterclass for Ainge and Boston’s front office in building a mountain of draft assets and also plucking some valuable young talent (Jae Crowder, Isaiah Thomas) in the midst of their rebuilding, which enabled them to turn back into a playoff team well ahead of schedule under Brad Stevens’ guidance.

Since then, Ainge has done his most important job well: Landing two emerging stars in Jaylen Brown and Jayson Tatum with top 3 picks in the 2016 and 2017 drafts, two moves that have given the franchise a greater margin for error with team building by still putting the team on a bright trajectory compared to others around the league.

However, in the wake of Gordon Hayward agreeing to terms with the Hornets over the weekend, it’s fair to start looking closely at yet another example of the Celtics losing a player for nothing during a period when they should be upgrading their contending chances. Maximizing assets can be the difference between a perennial playoff contender and a champion in the NBA and that has shown in the last few seasons.

Trade freeze

The list of useful players that have walked away from the Celtics in the past five seasons is a long one. Some left (Kelly Olynyk, Evan Turner, Jonas Jerebko) for obvious reasons earlier this decade, clearing the team’s cap room for max free agent signings in Gordon Hayward and Al Horford. However, in the last two years, there has been a lengthy list of stars and role players that have left or been traded by Boston with no meaningful compensation coming back towards the Celtics.

Terry Rozier
Marcus Morris
Aron Baynes (salary dump)
Kyrie Irving
Al Horford
Gordon Hayward
Enes Kanter (salary dump)

The max free agent names on this list will get the most attention, but the role players deserve notice too. Take last summer for example: Once Kyrie Irving and Al Horford elected to sign elsewhere in free agency, the front office opted to let their remaining free agents (Rozier, Morris) walk for nothing (on top of trading Baynes in a salary dump) in order to sign Kemba Walker to a max contract. On the surface, this is a completely defensible stance. However, it also could have been avoided.

Morris and Rozier were playing on expiring contracts and their long-term future with the C’s was in question for much of the 2018-19 season. Ainge had the ability to deal either or both ahead of the 2019 trade deadline to secure some kind of compensation before they walked for nothing in free agency. Instead, that deep ultimately dysfunctional Celtics team was kept together and bowed out in the second round to the Bucks in ugly fashion. Keeping Morris and Rozier (who was unhappy most of that season) ended up being an unwise gamble, resulting in a net loss of assets.

The same principle applies to the Hayward situation to a degree. Just one year earlier, the Celtics were burned when Al Horford got overpaid in free agency by another ‘contender’ in the Sixers, leaving the Celtics with nothing to show for what had been their biggest sign in free agent history. Ultimately, letting Horford walk for bigger money was the right call for the C’s since Horford’s contract is already an albatross, but the saga foreshadowed what was looming with Hayward this summer in free agency.

All it takes is one team to make an offer that’s beyond the C’s price range and that’s what the Hornets did. However, it was more than just that. By all accounts, Hayward preferred out of Boston in his next deal. He was the fourth option and wanted to be more. There would be no hometown discount and no guarantee the Celtics would win the bidding even if they were the top offer. The fact that the Celtics did not seem to have a great read on Hayward’s desires took away their chance at getting some kind of return for him when they could before free agency hit. They would not have received equal value for him at February’s trade deadline but they would have been able to secure a return that would be able to help in Boston beyond this season. Instead, the best they can hope for right now is a big trade exception (something they will have to give up draft picks to secure).

There’s an easy defense for keeping all of these expiring contracts in the moment before they walked in free agency and that’s the fact the Celtics believed they had a chance to win it all amid three runs to the East Finals in the last four years. However, Ainge really never pushed many of his chips to the center of the poker table in any of these seasons. Some of those choices were simply due to circumstance (young team, injuries to Hayward/Irving) but take note of Ainge’s dealing or lack thereof in the last five seasons.

2015-16: No trades in season (waive David Lee, 10-day)
2016-17: No trades in season
2017-18: No trades in-season (Signed Greg Monroe with disabled player exception after Hayward’s injury)
2018-19: Trade Jabari Bird in salary dump (2 way, 10 day RJ Hunter, Monroe)
2019-20: No trades in-season

That’s one in-season trade over five seasons for Ainge, which I think is safe to say is the lowest total for any team in the NBA during that time span. That lack of action for rosters that had flaws but also a good chance at getting to the NBA Finals in 2018 and 2020 looks questionable. Bad luck with injuries to Gordon Hayward and Kyrie Irving hurt the team in the postseason in 2018 and 2020 (with Hayward) but another useful veteran off the bench in either of those seasons may have made the difference on those squads in what ended up being tight matchups with the Cavs and Heat. Instead, Ainge not only stuck with talented rosters that lacked depth and had (arguably) too much youth but also held tight to a treasure chest of draft picks that have delivered lackluster returns outside of the top-10 in recent years.

Draft bets outside lottery have delivered limited returns

Since 2015, the Celtics have led the NBA with 22 draft picks used over that six-year span, which computes to an average of 3.7 per draft. Half of those picks were second-rounders (very tough to hit with) but the Celtics have selected 11 first round picks over that six-year span, which also leads the NBA during that stretch. They also have not consolidated picks to move up in the draft since 2013 (Kelly Olynyk at No. 13)

Here’s a closer look at the names and selections in recent years:

2015: No. 16 Terry Rozier (walked for nothing in free agency), No. 28 RJ Hunter (cut in year two), No. 33 Jordan Mickey (waived for cap room), No. 45 Marcus Thornton (overseas stash never made NBA)

2016: No. 3 Jaylen Brown, No. 16 Guerschon Yabusele (draft-and-stash bust), No. 23 Ante Zizic (draft-and-stash, traded for Irving), No. 45 Demetrius Jackson (two-way player for one year), No. 51 Ben Bentil (cut in training camp), No. 58 Abdel Nader (traded in salary dump to OKC in second year)

2017: No. 3 Jayson Tatum, 37 Semi Ojeleye, 53. Kadeem Allen (two-way player for one season), 56 Jabari Bird (traded to Atlanta after domestic arrest)

2018: No 27. Rob Williams

2019: No. 14 Romeo Langford, No. 22 Grant Williams, No. 33 Carsen Edwards, No. 51 Tremont Waters

2020: No. 14 Aaron Nesmith, No. 26 Payton Pritchard, No. 47 Yam Madar

Needless to say, the success rate after Tatum and Brown in the drafting department has not been great (Zizic, Yabusele, RJ Hunter were busts) with the jury still out on a number of guys (Grant Williams, Rob Williams, Romeo Langford, 2020 picks).

Despite having all of these picks in the last six years, the Celtics have not packaged picks to trade up on draft night since 2013 (when they moved up three spots to land Kelly Olynyk at No. 13). They have also not traded a first round pick for a player beyond Isaiah Thomas in 2015 and Kyrie Irving in 2017, taking 11 first round picks during that span.

Keeping and using picks is a very reasonable strategy but it has not been maximized by Boston in the past few seasons given the team’s depth chart. Many young players taken outside of the top-10 have either struggled in the NBA when given opportunity or have been stuck behind veterans, watching their trade value diminish in the process. It’s tough to hit in the NBA Draft outside of the lottery but the Celtics have had more chances to do that than perhaps any other team in the NBA over the past half decade. For a team with championship aspirations, their returns have been quite underwhelming from most of these non-lottery picks thus far. The team needs their most recent collection of picks (Langford, G Williams, Nesmith) to really pan out to help them build a strong bench.

So what exactly should the Celtics have done with all of these picks? A look at most playoff teams across the NBA over the past decade shows a pretty defined trend: Using draft capital to land veteran talent.

Clippers: Trade 2015 1st round pick for Doc Rivers, Trade 2017 first-round pick for Jared Dudley, Trade 2019 first round pick for Jeff Green, 2020 first-round pick for Marcus Morris, Three future first-round picks for Kawhi Leonard

Cavs: Trade 2015 first-round pick and Andrew Wiggins for Kevin Love, 2016 first-round pick to clear cap room to sign LeBron James, 2018 first-round pick for Larry Nance Jr. and Jordan Clarkson at trade deadline, 2019 protected first round pick for Kyle Korver

Raptors: 2017 first round pick with Terrence Ross for Serge Ibaka, 2018 first round pick to dump bad contract (DeMarre Carroll), 2019 first round pick and DeMar DeRozan in trade for Kawhi Leonard, two second round picks for PJ Tucker

Bucks: 2020 first round pick for Eric Bledsoe, 2021 and 2022 first round picks for George Hill

Pacers: 2020 first round pick for Malcolm Brogdon, 2016 first round pick (Caris LaVert) for Thaddeus Young

Heat: 2018 and 2021 first round pick for Goran Dragic, 2023 first round pick to salary dump Mo Harkless, Justise Winslow for Jae Crowder and Andre Iguodala

Warriors: 2014 and 2017 first round picks in salary dump to open up ability to sign Andre Iguodala, 2024 first round pick to dump Andre Iguodala

Spurs: No trades (no excess picks)

Jazz: 2019 and 2021 first round picks for Mike Conley, Trade up in 2017 draft to take Donovan Mitchell

Thunder: 2016 first round pick for Dion Waiters, 2018 first round pick for Enes Kanter, 2020 first round pick for Jerami Grant

Rockets: Trade 2015 first-round pick to dump Jeremy Lin, Trade 2016 first round pick for Ty Lawson, 2017 first round pick for Lou Williams, 2018 first-round pick for Chris Paul, 2019 first round pick in salary dump, Four future first round picks for Robert Covington and Russell Westbrook (separate trades)

Mavs: 2021 and 2022 first-round picks for Kristaps Porzingis, 2019 first-round pick for Luka Doncic,

Lakers: Three first-round picks, Brandon Ingram, Josh Hart and more for Anthony Davis

Nuggets: 2020 first-round pick for Jerami Grant

Needless to say, a lot of these teams were far more active with significantly less draft capital than the Celtics had over the past six years. The Celtics gave up one valuable pick in the Kyrie Irving trade but they have held tight to all of their other valuable draft assets in the past five years.

Ultimately, Ainge has been trying to toe the line a little bit too much it appears during the last few years between building for now (holding onto veterans until the end, leading to many walking away in free agency when C’s didn’t pay up) and building for the future (using all the draft picks). There were opportunities to land big names for the short or long-term (Kawhi Leonard, Jimmy Butler) that were passed on which could have better-maximized title chances. The same goes for elite draft picks (Luka Doncic) that the C’s had their eyes on.

The Celtics are still left in a good spot compared to the rest of the league with Tatum and Brown locked in place but their margin of error towards contending now becomes very thin with Hayward walking out the door for no meaningful compensation. Betting against Myles Turner (movable salary) looms large on this front as well if the C’s can’t piece together a Hornets sign-and-trade deal that lands them a big trade exception.

With Kemba Walker’s knee looking like a very big question mark going forward, the Celtics are very reliant now on Tatum reaching top-10 player status in order to contend. They also need the host of draft picks they have used in the past three seasons to start producing, but the odds of that happening for all the picks they took appear slim. As long as the C's are trying to contend, developing young players on the bench will be challenging to pull off at the same time, especially if there are veterans on the roster like Teague and Thompson that are proven commodities that are clearly in place for the present.

The hope now for the Celtics is that they didn’t miss their best chance to contend a few years ahead of schedule in the past couple of years. It's too early to judge Celtics on this offseason until we see if something comes out of the Hayward situation via another trade but the improvements made by the Sixers (Seth Curry, Danny Green), Bucks (Jrue Holiday), and Nets (Landry Shamet) in the past week really puts pressure on the C's. Tristan Thompson and Jeff Teague are solid signings but they aren’t ones that necessarily put the Celtics back in the top-4 of the East. With no more extra draft picks to wheel and deal with, the road to improvement gets a lot tougher. Years of playing it safe with trades and draft picks may come back to bite Boston.