Four Trade Ideas For Celtics To Flip Anfernee Simons

Brad Stevens is not trade-shy. Since entering the front office, Stevens has been involved in 27 trades

Brad Stevens is not trade-shy. Since entering the front office, Stevens has been involved in 27 trades. Okay, not all of them have been for players – a decent portion of them have been trading picks or moving back in the draft. Still, 27 trades since 2021 – I've had MyGM careers with fewer moves.

Let's recap those moves...

Trade 1 – June 18, 2021. Flipped Kemba Walker for Moses Brown, Al Horford and a 2023 2nd round pick and a 2021 first-round pick.

Trade 2 – July 31, 2021: Sent Moses Brown to the Dallas Mavericks for Josh Richardson.

Trade 3 – August 7, 2021: 3-Team trade

• Celtics got: Kris Dunn, Bruno Fernando and a 2023 2nd round pick
• Kings got: Tristan Thompson
• Hawks got: Delon Wright

Trade 4 – August 17, 2021: Sign-and-trade Evan Fournier to the New York Knicks

Trade 5 – September 15, 2021: Sent Kris Dunn, Carson Edwards and a 2026 second-round pick to the Memphis Grizzlies, got back Juancho Hernangomez

Trade 6 – January 19, 2022: 3-Team trade

• Celtics got: Bol Bol and PJ Dozier
• San Antonio Spurs got: Juan Hernangomez, a 2028 2nd round pick + cash
• Denver Nuggets got Bryn Forbes

Trades 7, 8 and 9 – All came at the February 10 trade deadline in 2022

• (7) Landed Derrick White from the Spurs, sent out Romeo Langford, Josh Richardson and a 2022 first-round pick
• (8) Flipped Fernando, Enes Freedom and Dennis Schroder to the Houston Rockets for Daniel Theis
• (9) Sent Bol Bol and Dozier, 2028 2nd round pick and cash to the Orlando Magic in return for a 2023 second-round pick

Trade 10 – July 9, 2022: Sent Malik Fitts, Juwan Morgan, Aaron Nesmith, Nik Stauskas, Daniel Theis and a 2023 1st round draft pick to the Indiana Pacers, got Malcolm Brogdon in return

Trade 11 – January 5, 2023: Sent Noah Vonleh and cash to the Spurs. Boston got a future 2nd-round pick

Trade 12 – February 9, 2023: Sent Justin Jackson and a 2023 2nd round draft pick to the Thunder. The Celtics got back Mike Muscala.

Trade 13 – June 23, 2023: 3-Team trade

• Boston Celtics got: Kristaps Porzingis and Marcus Sasser
• Washington Wizards got: Danilo Gallinari, Mike Muscala, Julian Phillips and Tyus Jones 
• Memphis Grizzlies got: Marcus Smart

Trades 14, 15, 16, 17: June 28, 2023 (Draft night)

• Trade 14: Boston sent Sasser to the Detroit Pistons, got back James Nnaji and a 2025 2nd round pick
• Trade 15: Stevens then flipped Nnaji to the Hornets for Mouhamed Gueye and Colby Jones.
• Trade 16: Stevens re-routed Jones to the Kings, got back Jordan Walsh and a 2024 2nd-round pick
• Trade 17: Gueye went to the Hawks in return for a 2027 2nd-round pick

Trade 18 – July 12, 2023: 3-Team trade

• Celtics got: a 2024 2nd-round pick via Spurs, a 2025 second-round pick swap via Mavericks and a 2030 second-round pick via Mavericks
• Mavericks got: Grant Williams, a 2025 second-round pick via the Spurs and a 2028 second-round pick via the Spurs
• Spurs got: Reggie Bullock and a 2030 first-round pick via Mavericks

Trade 19 – October 1, 2023: Stevens flipped Sixth Man of the Year winner Malcolm Brogdon, Robert Williams and a 2024 first-round pick for Jrue Holiday

Trade 20 – February 7, 2024: Out went  Lamar Stevens, a 2027 2nd round draft pick and a 2030 2nd round draft pick and in came Xavier Tillman Sr.

Trades 21 + 22 – February 8, 2024

• (21) Flipped a 2024 2nd-round pick for Jaden Springer
• (22) Sent Dalano Banton and cash to the Trail Blazers

Trade 23 – February 6, 2025: Sent Springer, a 2027 2nd round draft pick and a 2030 2nd round draft pick to the Houston Rockets. Celtics got back a 2031 2nd-round pick and a 2027 2nd-round pick

Trade 24 – June 26, 2025: Flipped the 32nd pick in the draft for the 46th and 57th via a deal with the Orlando Magic. The Celtics also got a 2nd round draft pick and a 2027 2nd round pick.

Trades 25 & 26 – July 7, 2025

• (25) Sent Holiday to Trail Blazers, got back  Anfernee Simons
• (26) Three-team trade
  • Celtics got: Georges Niang, a 2031 2nd-round pick and Cash
  • Hawks got: Porzingis
  • Nets got:  Terance Mann and Drake Powell 

Trade 27 – August 6, 2025: Stevens re-routed Niang to the Utah Jazz in return for a 2027 2nd-round pick and a 2031 2nd-round pick

Now, all eyes are on Trade 28, as Anfernee Simons is reportedly being shopped around the league. The problem is that Simons' $27.6 million salary for this season, coupled with his expiring deal, makes him a difficult player to trade.

Truth be told, I suck at fake trades. It's not something I do much of, and it's not something I think much about. BUT, I know some people have multiple ideas on how to move Simons and get fair value in return...SO, I drafted in some help on this one.

On Monday, I put out a post on Twitter and BlueSky asking for people's best and most realistic trade ideas for Simons. Today, I'm going to share some of them here and give my thoughts, as we imagine what Trade 28 could look like.

Trade Idea #1: Celtics Fix The Center Rotation

The first trade idea we have comes from "@NBA_QuachBoy" over on the (former) bird app.

In this scenario, Stevens would flip Simons in a 2-for-1 deal, adding some much-needed depth to the front court rotation in Jonathan Isaac and Goga Bitadze.

My thoughts on this trade idea: I've always liked Isaac's skill set, but his injury history has been a concern. However, he's played in 129 regular-season games over the last two seasons, averaging around 15 minutes off the bench.

If Joe Mazzulla can keep his minutes low and Isaac can add some high-level defense and rim-protection to the rotation, his presence would be welcomed. Isaac has enjoyed two strong years on defense, as illustrated by his Defensive Estimated Plus/Minus.

Isaac is entering the first year of a four-year $59 million contract. Not only could he help the Celtics now, but his salary also falls within the habitable zone for salary-matching purposes. I like the potential fit and the possibility of flipping him down the line.

Bitzade would also be a useful addition. He started 42 games for the Orlando Magic last season. And while I don't think Mazzulla would move away from Neemias Queta as the new starting big, Bitzade could put some pressure on him throughout the season. He would bring grit, physically and fill some of the void in terms of defensive rebounding.

My only concern with this deal is that there would quickly become a logjam at the five, unless Mazzulla and Stevens see a path for Luka Garza at the 4...This is something we touched on briefly when looking at 3 Ways Luka Garza Can Help The Boston Celtics Offense.

Likelihood of happening:

Unfortunately, the Magic recently acquired Desmond Bane, and for that reason, I struggle to see why they would give up legitimate front-court depth for an expiring Simons.

Likelihood: 2/10

Trade Idea #2: In Comes Malik Monk

Our second trade idea comes from "@TyStrongLong," also from the former Bird App.

This deal would see Malik Monk headlining the return for Boston. Once again, we're looking at a 2-for-1 scenario. Boston would be taking on three years of Monk's contract – the final year does have a player option – but at almost $9 million per year cheaper. They would also be taking a flyer on Isaac Jones, which fits the retooling mentality.

My thoughts on this trade idea: Monk could be a better long-term fit with the Celtics. At 27 years old, he fits the timeline with Jayson Tatum and Jaylen Brown. However, he's not the same level of scorer that Simons is, I mean, he shot 32.5% from deep last season on 6.6 attempts per game. Still, I think he's a slightly better defender and a talented playmaker.

If the Celtics don't believe Simons will take a pay cut on his next deal and are willing to trade some of his offense for additional ball-handling and shot creation, moving for Monk could work. The Kings are reportedly open to moving on from him. As for Jones, I don't know enough about his game – he's not someone I've seen any film on. So, I'll avoid making baseless claims there.

Likelihood of happening:

If Stevens values the $9 million savings and a tradable contract worth $19.4 million per season, swapping Simons for Monk makes sense. Mazzulla may welcome so additional on-ball creation and interior scoring too. If this offer crossed Boston's desk, I don't think they would throw it out right away. I'm also not sold on whether they would push forward with it either.

Likelihood: 5/10

Trade Idea #3: Bringing Back Grant Williams

Shoutout to the venerable Bill Sy for this one! The trade idea also came from Twitter, but Bill has been my editor extroardinaire over at CelticsBlog for years – he's also one of the best people you will ever have the pleasure of coming across. A true legend.

Bill's trade proposal would see the Celtics do business with the Charlotte Hornets, bringing back Grant Williams along with Josh Green in return for Simons.

As a quick side note, Bill's reply on Twitter said "and picks," so I quickly added two future seconds to the trade idea – you can debate whether those would be enough for the deal to get done.

My thoughts on this trade idea: I'm a little biased here, as I was a big Grant Williams guy during his one season under Ime Udoka. Still, he would bring some much-needed versatility to the front court. We know he can hit the three. We know he can work with his back to the basket. And, we know he can defend multiple positions along the front court.

Bringing Williams back would give the Celtics a versatile forward who can spell minutes as a starter or off the bench. However, he would also likely spell trouble for Jordan Walsh, as he would likely emerge as the odd man out, because I expect Mazzulla to give Hugo Gonzalez plenty of opportunity to impress.

Green would also be a good addition. He can knock down threes, guard his yard and has a little bit of burst when needed. What I like is that he won't need too much of the ball, and could work in the starting unit or off the bench.

For the Hornets, a rotation of LaMelo Ball, Simons, Brandon Miller, Miles Bridges and whoever they want at center would be exciting and offensively electric. However, I'm not sure Charles Lee would be thrilled with the non-existent defense that rotation would offer.

Likelihood of happening:

I think the Hornets could be tempted into adding another scorer who can create for himself and others. However, Simons contract and limited defense could be a stumbling block. I'm not sure losing Williams or Green would be too much of a concern for them, either. I think both sides would at least give this package some strong consideration.

Likelihood: 7.5/10

Trade Idea #4: A Three-Teamer

The last of our trade ideas for today.

"@GeneralGrantW" is the architect of this 3-Team masterpiece. The deal would involve the Nets, Celtics and Philadelphia 76ers.

"BRK gets a star that they can market to sell tickets who won't affect their tank, and hit minimum payroll, and a juicy pick," @GeneralGrantW wrote in his comment. "PHL gets Simons (reportedly interested) and gets off the PG contract. BOS gets closer to under the tax and a 6'11 guy on a descending pay scale for three years."

My thoughts on this trade idea: The biggest stumbling block to this trade idea would be whether the Sixers are ready and willing to cut ties with Paul George after just one season with the franchise. The second stumbling block would be whether the Nets want to take on that contract.

However, if both Brooklyn and Philly were open to the George segment of this trade idea, I think the Celtics would jump at the chance to add Nic Claxton. They would be getting a high-level rim-runner who can offer legitimate vertical spacing on the roll, and reliable rim-protection on defense. And we know Tatum loves playing with a lob threat, too...

Philadelphia would also add another young guard to its growing collection, which may or may not be an appealing option. Nick Nurse would then have Tyrese Maxey, Jared McCain, VJ Edgecombe AND Simons to choose from...And that's before we know what happens with Quentin Grimes. That logjam may be too much, and could be a key reason why this trade, while beneficial to Boston, wouldn't materialize.

Likelihood of happening:

While @GeneralGrantW has given very fair reasoning as to why each team would potentially be open to this deal, there's a lot of moving parts involved. Brooklyn would need to be ok with adding George and his mammoth salary, and the Sixers guard logjam would need to be overlooked.

I do think there's logic to each part of this deal, but getting three teams to agree is never easy. Still, the framework is solid, and I would love to add Claxton to Boston's rotation. Unfortunately, I just keep coming back to the George and the logjam of it all, and that's enough for me to think this idea would be too good to be true.

Likelihood: 3.5/10

Drop your trade ideas in the comments!

I really enjoyed looking at some of the trade ideas people commented on Monday. I think it shows the opportunities the Celtics potentially have in moving on from Simons while also illustrating how limited the market likely is for him due to his expiring contract and sizable salary.

I would like to think Stevens can move Simons without attaching a pick to get it done. Unfortunately, that may be wishful thinking. Still, I do lean into the proposal that lands Williams and Green; I can see how that could be enticing for both sides.

Let's keep this going! Drop your trade ideas for Simons in the comments. And if you don't have a trade idea, share your thoughts on the ones above, or the ones other people share below! And if you would prefer Boston keep Simons around, then let us know that, too!

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