It's Thanksgiving week in a pandemic and no one wants to be ungrateful so I'll limit my Celtics front office take to a tweet thread instead of going Full Posting. It follows below...
The current issue with the front office is not simply that they "allowed" major unrestricted free agents to leave. I agree that in at least 2/3 major cases the players received contracts the C's should not have paid. In the case of Hayward, it might still work out ok.
The issue is that the last three seasons following the (amazing) Tatum selection have been marked by a pairing of inaction on both short and long-term moves that resulted in a middle that didn't produce a title and did leave them exposed to those players leaving.
If the team didn't want to pay Horford and Hayward's next deals, they should have either traded them before it was possible for them to walk or, If they believed they were close enough to a title to be worth keeping them, they should have pushed other chips in to support that.
As @BrianTRobb notes, they have made ONE in-season trade in the last five years (dumping Jabari Bird). Meanwhile, these players have left for at most a TPE and in some cases the Celtics have given and asset to salary dump them instead of using them earlier in a "buy" trade...
Kyrie
Horford
Hayward
Rozier
Olynyk
Morris
Baynes
Kanter

Nader and Poirier we paid cash to dump. Yabu got stretched. Theis might get added to this list next year.
Meanwhile, multiple picks have been used to trade into future diminishing assets, take stash players for their status instead of their talent level, or to clear relatively small amounts of cash from players that were not awful.
If we had to stay committed to the 2nd/3rd tier stars who ended up leaving via free agency because we were contenders (I disagree but am not all-knowing), those picks and lower level players who left should have been packaged for win-now moves.
If the picks were valuable as a pipeline to the future of the team built around the Nets pick haul, at least one of the bigger salary players should have been moved before they could walk for nothing.
Some things ARE just bad luck and you don't have to be all-in on one strategy. Until you get far down the line on one path you shouldn't be, imo. But you also shouldn't just take moments of poor luck or stupidity from competitors and use that as a cover to ignore everything else.
It's also a trend that has to stop and if you deny that it's even a problem you're unlikely to stop it. The decision to sign Kemba was complicated. What's not complicated is that the C's can't be a mid-tier contender for two more years and then see him leave for nothing.
On the smaller scale, they can't have Tristan take a rotation place that ends in Theis being a backup who blocks Timelord just long enough for both to become roster casualties, too. If they pay to make Hayward a S&T that TPE can't be sat on until it turns into nothing of note.
In general, I think patience is better than eagerness in NBA team building but it's a balancing act and I think it's difficult to look at recent results and think that the front office has had the balance right.
This is not a call for firings or setting out a belief that they're screwed forever. The Tatum selection and development of Brown gives them a lot of equity even beyond the 2008 title, which is fading into a pretty distant past.
It is a call for introspection on why decisions (many of which I supported) have not worked out and a willingness to admit that so that the current, still promising, situation can start to move in a more clearly positive direction.
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