The Celtics’ Anfernee Simons Dilemma

To trade or not to trade

Over the next 11 days, we’re probably going to see the Boston Celtics linked with a merry-go-round of players. Most of them will probably be big men.

• Ivica Zubac

• Jaren Jackson Jr.

• Nikola Vucevic

• Nic Claxton

• Yves Missi

• Day’Ron Sharpe

• Jarrett Allen

• Myles Turner

Some or all of these names will find their way into trade proposals, with the Celtics being their landing spot. 99.9% of those proposals will be conjecture. I’m sure most of us will dabble with the trade machine in our free time. And I’m certain I’ll be aggregating some of the stuff that drops (hey, gotta pay the bills!)

However, for most of those trade proposals to work, Anfernee Simons will need to be part of the hypothetical trade package.

The same Anfernee Simons who dropped 21 points against the Chicago Bulls last night, on 50% shooting, no less.

The same Anfernee Simons, who is second in the NBA for made threes in the month of January (Sam Hauser is first).

The same Anfernee Simons who is averaging 16.1 points, 3 rebounds, and 3 assists since New Year’s Day.

And the same Anfernee Simons who dropped 39 points on the Miami Heat on Jan. 15.

After a slow start to the season, during which he was adjusting to a new city, new team, new style of play, and new role off the bench, Simons has started heating up.

In return, interest in his services is likely starting to rise, especially among teams that need an additional scoring boost off the bench. And, for the Celtics, it makes sense to explore what Simons’ trade market looks like. After all, from the moment he got off the plane at Logan, he was viewed as a future trade chip — someone who could help land another high-level starter when the time is right.

Well, the time is right.

The Celtics are second in the Eastern Conference. They look every inch a contender in the Eastern Conference. If you buy-in to the increasingly likely notion that Jayson Tatum will be back before the end of the season, then you’re probably already scheduling your mid-year plans around the postseason.

Let me ask you this, though: Do the Celtics need a starting-level big man more than they need Simons for the second half of the season?

If you had asked me before the start of the season, my answer would have been a resounding yes. I had no faith that Neemias Queta and Luka Garza could anchor the middle of the floor to the level they currently are. In truth, I still believe another big is needed — someone capable of being the starting center on a championship team.

But is it worth giving up Simons?

Well, that depends on what you think will happen in the summer.

If you think Simons will book it out of Boston to sign elsewhere, then yeah, making a move now is 100% the right choice. Better to lose him in January with something coming back in return than in the summer when his absence creates a void.

But, if you think both he and the front office would have an interest in extending the current partnership…well, now things get a little tricky.

Simons is arguably the Celtics' last big bite of the trade apple, in the sense that he’s an expiring contract that’s sizable enough to dangle in trade talks for a high-level talent. His expiring contract could make him valuable to other front offices around the league, if only for being cap relief once the summer rolls around.

If Boston keeps hold of Simons, they will still have their $22.5 million TPE from the trade that sent Kristaps Porzingis to the Atlanta Hawks. However, you can’t aggregate players’ salaries in a deal that uses a TPE. So, it’s not like the Celtics can go and get Zubac, making $18 million per year, with a package built around multiple guys and draft assets, and use the TPE to absorb his contract.

Would the Clippers be happy with a Hauser + picks for Zubac deal? Pritchard + Picks? Maybe Hugo Gonzalez and draft assets? Because that’s how the package would look. And that’s before we even look at how that type of move would hit the Celtics cap sheet…Can you say second apron?

No.

Trading Simons is the easiest route to an immediate upgrade.

However, in the same breath, you’re weakening the guard rotation as a result. Suddenly, you’ve got White and Pritchard. That’s it. Ok, you can slide Baylor Scheierman into a guard role. Jaylen Brown has spent enough time there, too.

But in terms of a difference-maker off the bench, in the same vein as Pritchard was last season and Simons is this year, nope, that doesn’t reside on the current roster.

Instead, Stevens would need to supplement a Simmons trade by moving for another guard. I like Ayo Dosunmu in that instance. Again, though…What do you have to give up to make that happen? And is Dosunmu going to re-sign?

There is a third option.

A summer sign-and-trade.

Now, these aren’t easy to pull off. It also requires another team wanting Simons so much they’re willing to work with being hardcapped at the tax apron.

More importantly, Boston would be highly unlikely to get a player such as Missi, Sharpe or Claxton. Instead, it would likely be second-round draft picks and another TPE. In reality, it wouldn’t solve much. But it had to be mentioned for the sake of covering all bases.

So, this raises the question: Has Simons’ play since December, and especially in January, made him untradable? Or has it made him more tradable?

The irony is that Simons was acquired, in my opinion, to be moved at the trade deadline. Now that he’s playing well enough to justify that plan, he’s also playing well enough to complicate it. He’s both more and less tradable at the exact same time.

For me, that means you only sign off on a trade that makes you unequivocally better. You do it for the Zubacs and the Claxtons of the trade market.

If you can get a Sharpe on the cheap, then you snap him up, keep Simons and get to negotiating an extension. In part, Simons’ future will depend on what the market provides — and that sucks, both for him and for any of us trying to figure out what’s going to happen.

We also have the obvious caveat that Stevens works in silence. It’s highly likely that even if Simons does get traded, it’s not for any of the names listed above. Outside of Jrue Holiday, Stevens has worked in the shadows.

The fact is, we’re looking at an uncomfortable truth: The Celtics’ best trade chip is also one of their most stabilizing players. Simons has made himself valuable enough to trade and valuable enough to keep all at the same time.

What would you do?