Revisiting the draft gamble that haunted the Celtics in 2020

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The NBA Draft has been a bit of a rollercoaster for Danny Ainge and the Celtics' front office in the past decade. There have been tremendous hits at the top of the draft (Jayson Tatum, Jaylen Brown, Marcus Smart) along with some unfortunate misses (James Young, Guerschon Yabusele, RJ Hunter) in the bottom half of the first round as the team has gone through an impressive stockpile of draft selections since embarking on an expedited rebuild from the end of the Paul Pierce/Kevin Garnett era.

That well of extra draft assets is about to run dry however next month since the 2020 NBA Draft will mark the end of Boston’s excess draft picks in their collection (Memphis at No. 14, Milwaukee at No. 30). Some wheeling and dealing on draft night for future selections could change that outlook but with the Celtics in win-now mode, punting assets towards the future is a risky path (albeit a potential smart one if they want more picks to save for an in-season deal).

The Celtics have had their share of good and bad fortune when it comes to their treasure chest of picks during the last seven years. For as much good fortune as they received with maximizing their Brooklyn first round picks in the lottery (No. 3 in 2016, No. 1 in 2017) the tides have turned in the past two seasons. First, the Kings surprised expectations in 2018-19, what was expected to be a pick in the top half of the lottery went to No. 14 overall (Romeo Langford) in the 2019 NBA Draft. Last season, the Memphis Grizzlies also broke out behind Rookie of the Year Ja Morant to turn another potential top-10 selection in a mid-first round pick.

While the Celtics had no control over some of this misfortune, there remains one understandable but painful miscalculation the Celtics made that continues to haunt them.

It all goes back to one of Ainge’s best moves as general manager: Trading down from No. 1 in the 2017 NBA Draft to land Tatum at No. 3. Ainge not only got the best player in the draft at No. 3, but he secured a smaller salary for him on the draft scale by taking him at No. 3, which proved to be extremely useful for cap management that offseason when the C’s signed Gordon Hayward. Tatum is now a franchise cornerstone, which ensures the main part of this deal will always be looked back on fondly by fans.

The other aspect of the Celtics deal with the Sixers that was negotiated for months according to a league source was the pick protections on the additional pick that went back to Boston on top of the No. 3 overall selection in the 2017 NBA Draft.

As a reminder, here are the terms the Celtics agreed upon from Philadelphia for that future first-round pick:

—A 2018 Lakers first-round pick (only conveys if it lands in No. 2-5)

—If that Lakers pick did not convey, the Celtics would get a 2019 top-1 protected pick from the Kings or Sixers (whatever pick was higher).

According to a league source familiar with the trade talks, the Celtics were adamant about having the Lakers 2018 first-round pick only convey in the 2-5 pick slots in negotiations, in hopes they would be able to maximize their chances of getting a top-tier player for giving up the No. 1 overall pick.

Hoping the Lakers bottomed out in the 2017-2018 season was a fair expectation given their young/rebuilding roster at that point in time. The Celtics brass also again made a calculation that the upside of a high potential pick from the Kings in 2019 (two years out) would outweigh a highly probable lottery pick that would arrive in 2018, even if it failed to land in the top-5.

We all know how this story finishes when it comes to the present day. The Lakers (32-5) were bad in 2017-2018 but not bad enough to land a top-5 pick (they finished with the No. 10 pick in the lottery). That meant the Celtics' pick compensation from the Sixers deal rolled over to 2019, which ultimately left the C’s with Langford (No. 14 overall) after a surprisingly strong season from the Kings (39-43) in 2018-19 pushed them to the bottom of the lottery.

The No. 14 overall pick two years later is a pretty low price to pay to move up from No. 3 overall to No. 1 overall in any NBA Draft but that’s the risk the Celtics ran by punting the potential draft asset so far down the line. Just like the C’s benefitted from no one foreseeing the extent of the Nets' demise in the late 2010s after the KG/Pierce deal, they suffered from the unforeseen rise of the Kings during the 2018-19 season (albeit a brief rise).

So how does all of apply to the present day?