Boston Celtics

What move should the Celtics make before the NBA trade deadline? Our writers weigh in.

Chad Finn and Tom Westerholm go 1-on-1 on the Celtics before the NBA trade deadline.

Danny Ainge Brad Stevens
Danny Ainge and Brad Stevens. Jessica Rinaldi/Globe Staff

COMMENTARY

The NBA trading deadline arrives Thursday at 3 p.m. With his Celtics in the midst of a chaotic and thus far underwhelming season, president of basketball operations Danny Ainge might just turn some rumors into action this year.

Columnist Chad Finn and reporter Tom Westerholm, a respected Celtics beat writer, conversed at length via email this week to try to sort out why the Celtics have underwhelmed, and what they could do at the deadline to restore contender status in the Eastern Conference. This is their conversation:

Finn: I suppose we should  address the broader issue before we dig into what Danny Ainge’s approach should be at the trade deadline: What’s the biggest reason from what you’ve seen why this team has failed to meet expectations this season?

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As we began this thread, they were 21-21 and in sixth place in the Eastern Conference, bunched in with lower-expectation teams like the Knicks, Hornets and Hawks. Through 42 games last year, they were 28-14 after clobbering the Lakers by 32 points on January 20.  A loss to the Grizzlies Tuesday dropped them back below .500 and into eighth place.

A similar record would have been a reasonable expectation for this season, but they’ve just never been able to gain any momentum. They played cohesively in Sunday’s win over the Magic, and about as well as could be expected without Jayson Tatum and Kemba Walker Tuesday vs. Memphis. Now they have a grueling stretch ahead, including two with the Bucks.

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Obviously, there are a lot of factors to the underachievement. But what’s the biggest, Tom? I’ll get into my answer after I hear yours.  Take the first shot.

Westerholm: We can list issues for days. Kemba isn’t 100 percent, and the Celtics were counting on him to be an All-Star. My son’s plastic kiddie pool is deeper than this roster. There are several new faces present, and COVID wiped away the bulk of their opportunities for building chemistry and continuity.

But I think the biggest factor is the talent exodus since the 2018-19 season ended, which is pretty staggering. To echo Danny Ainge and Brad Stevens all season: That’s not an excuse, and this team’s failures are their own. But in retrospect, expecting a team to be contender-adjacent after watching Kyrie Irving, Gordon Hayward, Al Horford, Terry Rozier and even Marcus Morris walk was probably a little rosy, even adjusting for growth from Jayson Tatum and Jaylen Brown.

The Celtics lost five players who together could be the starting lineup for an Eastern Conference playoff team. Depth was always going to be an issue, and I feel like I/we probably should have seen that coming.

There are other factors beyond their control (Hayward’s injury, for example), but those probably get too far into the weeds. Where do you land?

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Finn: You hit on something that really bothers me there: The lack of context or perspective from a loud segment of the fan base that doesn’t understand – or doesn’t care to understand – why they are in this predicament.

[Begins shaking fist.] They’re known as the “Fire Trader Danny” people, who have some, but not total, overlap on the Venn Diagram with the “Brad is a college coach/too passive” people and the “It’s all about banners and nothing else because WE’RE THE CELTICS” people.

Ainge, like every other personnel judge, has made some mistakes. I’m really tired of watching Tristan Thompson grab an offense rebound, refuse to kick it out, and get some awkward lefty half-hook swatted off his forehead.

But he’s also done a remarkable job of rebuilding this team, multiple times due to unforeseen circumstances, after sending Pierce and Garnett to the Nets in 2013. He stole Isaiah Thomas from Phoenix and turned him into Kyrie Irving, more or less. He signed coveted All-Stars Gordon Hayward and Al Horford. It stinks that Kyrie quit on them – and quit is the right word. It stinks that Hayward snapped his leg in his first game. It was unforeseen that Horford would leave as a free agent. There are going to be a lot of what-ifs about this era.

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The degree of difficulty has been ridiculous, and yet Ainge got it right with the two most important elements post-New Big 3: He drafted Jaylen Brown. And he drafted Jayson Tatum. A high percentage of the fans that want to fire him coveted a Kris Dunn/Markelle Fultz backcourt, and you can’t tell me otherwise. Ainge is a damn good de facto GM. [Stops shaking fist.]

But to actually answer the question, the biggest issue is that Tatum and Brown have good intentions, but when things start to go wrong, they feel like the best thing for the team is for them to try to create their own offense, and that’s when it starts looking like they’re taking turns.

Both need to learn to make their teammates better. They also need some better teammates. How does Ainge get them some? What is your absolute ideal for what Ainge could do with the TPE, and what do you think he will do?

Westerholm: A concerning aspect of the Celtics’ trade deadline is that when you ask for my “absolute ideal,” the honest answer is “I’m not sure” — not because I’m concerned about being locked into a take but because I really don’t know what moves the needle sufficiently.

Is Aaron Gordon or John Collins the building block Tatum and Brown need to get to the next level? I’ve long leaned toward Harrison Barnes both because he seems like a great guy who would happily fill a complementary-starter role and because he looked like the most cost-friendly option, but recent reports suggest he might not be cheap to pry away from the Kings.

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I certainly see the value in using the TPE now, since 1) you get a useful player for the postseason and 2) it becomes use-it-or-lose-it this offseason, and teams will certainly try to exploit that. To me, acquiring Gordon — a versatile forward who is only 25 — without giving up Marcus Smart is probably the best-case scenario.

But I could see an unenthused Ainge examining the landscape and simply trading for Nmenja Bjelica. There’s probably some value in holding onto assets in case Jayson Tatum’s best friend becomes available this summer. What’s your ideal?

Finn: Trading Carsen Edwards and all the second-round picks for eternity for that Friend of Tatum, Bradley Beal. I’ll have to check to see if the salaries match first before Ainge can call it in.

The ideal in the real world? Barnes. I like him for the same reasons you do, though I already dread hearing from Celtics fans that will call him the new Jeff Green after his first 3 for 14 shooting performance. (Barnes, Game 5-7 of the 2017 Finals: 32 shots attempted, 5 shots made. Ouch.) He’s a well-rounded, selfless player who knows who he is, though, and contrary to what so many seem to think, they don’t need a big, they need a versatile wing/playmaker.

I’d like Gordon, who is still only 25 and a decent playmaker beyond his obvious athleticism, if they can do it without cutting the heart out of the team and including Marcus Smart. Trading him to me is a non-starter, even if there is anecdotal evidence that he’s slipped ever -so-slightly as a defender.

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There will be a lot of yelping if he doesn’t do anything, but I’m fine with Ainge kicking the Gordon Hayward TPE to the summer. I don’t think he’ll be influenced by public opinion, either.

I’m an optimist about this team in general over the next couple of seasons – Brown and Tatum have elite ability, and their hearts are in the right place, but they haven’t figured out how to best deploy their talents for the maximum benefit of the team yet — , but I do wonder if this is just one of those seasons where everything is going to conspire against them right up until it’s abruptly over.

I don’t think they’re winning the East in a best-case scenario this season, and I’d rather watch Payton Pritchard, Aaron Nesmith and — if he can manage to get back on the court some time before his 30th birthday — Romeo Langford get minutes to enhance their chances of becoming meaningful contributors next year. I believe in both of them, and one of Stevens’s blind spots is giving minutes to low-ceiling veterans over erratic but talented kids. Play the mistake-makers, Brad.

Westerholm: Play the mistake-makers” is a great way to put it. I was high on both the Nesmith and Langford selections — Nesmith is a good shooter, and Langford is a heady pick-and-roll playmaker who has been largely utilized as a 3-and-D option so far — and I would love to see them both get more consistent minutes.

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And you didn’t even mention the most talented mistake-maker: Rob Williams, whose minutes have been limited even though he says his hip feels great.  If the Celtics spend some time turning those players into contributors (or valuable trade chips on the off chance that Carsen Edwards and second-round picks don’t get a deal done for a star), that’s pretty solid business.

I’m with you on winning the East as well — I don’t think there’s a deadline move that puts the Celtics in a position to pull it off short of a blockbuster. This trade deadline feels incredibly consequential partly because the Celtics have struggled and — I imagine — partly because everyone is looking for something to be happy about after spending the last year inside.

But whether or not the Celtics use the TPE, I think bigger questions are coming this offseason. Tatum and Brown are signed long-term, which is a great starting point. But if the Celtics aren’t contenders, what’s next? The aforementioned talent exodus paired with Walker’s struggles will force Ainge to be creative in his team-building, and I wonder if that’s part of the reason he seems hesitant to use the TPE now.

In any case, my summation with the deadline approaching is that the Celtics are in a better position than one would think after watching them lose to the Sacramento Kings last week, but not nearly as promising as we might have thought as recently as the summer of 2018. Does that feel like a fair place to land?

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Finn: That place of landing could not be fairer. But if they trade Smart, I’ll be in no mood for fair, and might quit following sports altogether. Might even quit society. Hermit life ain’t so bad.

Westerholm: He’s better than Aaron Gordon! By himself!

Finn: By himself. Hear that, Danny?

Profile image for Chad Finn

Chad Finn

Sports columnist

Chad Finn is a sports columnist for Boston.com. He has been voted Favorite Sports Writer in Boston in the annual Channel Media Market and Research Poll for the past four years. He also writes a weekly sports media column for the Globe and contributes to Globe Magazine.

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