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On a sleepy pre-New Year’s Eve Saturday afternoon, the Toronto Raptors and New York Knicks swung a massive NBA trade. This trade agreement makes six consecutive seasons the NBA has seen a trade happen within weeks of trade season unofficially opening on December 15.

Here are the particulars:

  • New York Knicks acquire: OG Anunoby, Precious Achiuwa, Malachi Flynn
  • Toronto Raptors acquire: RJ Barrett, Immanuel Quickley, 2024 Detroit Pistons second-round pick

This is a somewhat rare trade between division rivals. This is especially true when both teams are currently pursuing postseason spots this season. And, if that wasn’t enough, both teams are embroiled in a lawsuit over a front office employee taking proprietary information with him when the left New York for Toronto this past summer.

However, none of that kept the two from coming together on what looks like a win-win trade. Let’s dive in!

New York Knicks

Incoming salary: $26.9 million in 2023-24

Outgoing salary: $28 million in 2023-24

The New York Knicks have not been a Tom Thibodeau style of defensive team over the last three seasons. After finishing third in the NBA in defensive rating in 2020-21, the Knicks have been 11th and 19th the last two seasons and currently sit a pedestrian 16th this season.

In addition, the Knicks have been an average or below-average three-point shooting team over the last few years.

Enter OG Anunoby.

Anunoby has been one of the NBA’s premier 3&D wings throughout his seven-year career. He’s consistently hit in the high-30% range on a healthy volume of attempts from deep. Defensively, he uses his 6-foot-7 frame to guard anyone 2-4. Anunoby is also quick enough to switch onto point guards, while being strong enough to switch onto centers.

The challenge is that Anunoby’s game has never leveled-up the way many hoped it would. When he signed his rookie extension, the hope was Anunoby would grow into more of an on-ball threat. That’s never really materialized.

Despite being a solid ball-mover, Anunoby isn’t a shot-creator. He’s dependent on others to get him good looks. That’s limited his upside as an offensive player.

On defense, Anunoby is a very good defensive player. However, as a wing, he’s not someone you can build your entire defense around. So, while he may continue to earn accolades for his individual defense, he’s not someone who can lift an average team defense from poor to good or good to great all by himself

In New York, Anunoby shouldn’t have to worry about doing any of those things on either end of the floor.

On offense, the Knicks have enough creators that Anunoby’s ability to consistently hit open threes will be welcomed. He’s a major upgrade over RJ Barrett in the phase of the game. Barrett is more likely to put the ball on the floor and to create something, but that’s less of a need when Jalen Brunson and Julius Randle are around.

On defense, Anunoby being a bit bigger than Barrett is helpful. He’ll be able to slide up a position to play the four when Randle needs to sit, which is something Barrett can’t do. Anunoby’s ability to lock down one perimeter player, will also help the Knicks in hiding Brunson, while letting everyone else stay home more.

Expect New York’s starting lineup to look like this now:

  • Isaiah Hartenstein
  • Julius Randle
  • OG Anunoby
  • Donte DiVincenzo
  • Jalen Brunson

Behind that group, New York will have Josh Hart, Quentin Grimes, Precious Achiuwa and Taj Gibson.

It’s the second-unit where the Knicks downgraded. Malachi Flynn has played better this year, but he’s not a replacement for Immanuel Quickley. That’s a big loss for New York. One silver lining: This does clean up the guard/wing rotation quite a bit. The Knicks had been trying to fit six players into what were really two spots. Someone was always getting shorted minutes, and that’s no longer an issue.

Achiuwa will help with frontcourt depth. Thibodeau is likely use him exclusively as a backup center, as opposed to having him play the four, which Toronto dabbled in. Mitchell Robinson is out for the season, which has pressed veteran Gibson into service behind Hartenstein. Putting it kindly, Gibson’s best days are behind him. Achiuwa will bring energy and the ability to run the floor behind Hartenstein.

Looking beyond this year, this trade has the initial feel of cleaning up New York’s cap sheet. However, that’s taking way too simplistic of an approach.

Yes, the Knicks shed over $100 million in salary for Barrett. And New York doesn’t have to pay Quickley in restricted free agency this summer, where the rumor was he wanted at least $100 million of his own. But the Knicks will need to pay Anunoby, and that’s going to eat into their cap flexibility a good deal.

There are basically three options for Anunoby’s next contract. He could sign an extension right now, but he’s limited to coming in under the extend-and-trade parameters. That would mean declining his player option for next season and signing a two-year extension worth about $40.1 million. Under the extend-and-trade rules, Anunoby would be limited to a 5% raise off his current $18.6 million deal. That would be about $19.6 million for next season, followed by a second year in 2025-26 at $20.5 million.

That’s a little light for what Anunoby could expect to get in free agency or via a standard veteran extension.

If this trade is completed on December 30 (and it’s expected it will be), Anunoby will be eligible to sign a standard veteran extension on June 30, when his six-month extension restriction would lift. That extension would be worth as much as $116.9 million over four years. That would see Anunoby declining his player option for next year, but extending for the max of four years, with a 40% raise from his current salary and then 8% raises after that.

That’s an average annual value (AAV) of about $29.2 million. That AAV is far more in range of what Anunoby could be looking at on his next deal, compared to the $20 million AAV he could extend for right now.

But, there’s a complicating factor here. Anunoby could choose to not extend and to play things out to unrestricted free agency this summer. He’d be eligible for a projected first-year max of $42.6 million as a free agent. That’s either from the Knicks or another team. Because New York has his full Bird rights, should Anunoby opt out this summer, they can give him up to that $42.6 million, and could add a fifth year onto the deal.

Now, Anunoby probably isn’t a max player. But he’s close to one. And because his skillset as one of the best 3&D players in the league can fit anywhere, he’ll be a prime free agent target for any cap space team. There are teams that have enough cap space to make Anunoby a max or near-max offer. That could force the Knicks to pay a bit more than Anunoby could fetch via an extension on June 30.

Putting it all together, there is no way Anunoby extends now. He’d be leaving too much money on the table. By the time June 30 rolls around, he’ll know if he should extend with the Knicks for just shy of $30 million AAV, or if he’s got bigger offers waiting for him in free agency. Or if he can simply get more, or a fifth year, from New York as a free agent.

As for Achiuwa and Flynn, they are both eligible for restricted free agency this summer. The Knicks will likely take a wait-and-see approach with both players. Achiuwa could be someone New York will invest in as a restricted free agent. Hartenstein will be an unrestricted free agent this summer, and Mitchell Robinson will be returning from a season-ending injury. If Achiuwa plays well the rest of this season, it’s easy to envision a world where he sticks in New York.

Flynn will probably be allowed to leave, as the Knicks already have other guards. And they like Miles McBride, who they’ve developed over the last few years and is in a similar spot to Flynn as a restricted free agent point guard.

Jumping back to this year: don’t expect New York to be done tinkering with their roster. This trade saved them some money on this year’s books. The Knicks are about $5 million below the luxury tax line and about $10 million under the tax apron, at which they are hard capped. That should be enough wiggle room to make additional moves, should the opportunity arise.

New York still has Evan Fournier’s pseudo-expiring $18.8 million contract (there is a $19 million team option for Fournier for 2024-25) to dangle in trade talks. If New York decides they need to upgrade another spot (center perhaps?), they’ve got that contract and enough room under the tax and apron to make it happen.

Toronto Raptors

Incoming salary: $28 million in 2023-24

Outgoing salary: $26.9 million in 2023-24

This trade signals the start of a reset for the Raptors. No more clunky three-forward lineups. No more searching for a long-term answer at point guard. This trade made Toronto more balanced, and they might not be done making moves.

RJ Barrett is a more versatile offensive player than OG Anunoby. Barrett is a better off-the-dribble creator than Anunoby is, and he’s a better playmaker than his assist numbers show. If he’s given a chance to do a little more on-ball creating in Toronto, Barrett could shine.

Barrett isn’t nearly the shooter Anunoby is, and that’s tough for a Raptors team that all too often struggles to make jumpers. Outside of hitting 40% in his sophomore season, Barrett has been a below-average three-point shooter. This season he’s ticked up slightly, but the idea of him becoming a good shooter is a thing of the past.

Defensively, Barrett is a notch or two below Anunoby too. He’s smaller, so he’s not as fully switchable as Anunoby. He’s much more of a pure wing defender. But Barrett is a good defender and should fit in well alongside Toronto’s other wings and forwards.

Where the Raptors did well on the court in this trade was snagging Immanuel Quickley. After breaking out last season and nearly winning Sixth Man of the Year, Quickley has been even better this season. And that’s despite losing playing time and some shots in a crowded Knicks backcourt.

Essentially, Quickley is a player whose profile screams a need for a bigger role. He’ll get it in Toronto. Dennis Schroder has played well for the Raptors, but he’s best as a backup at this point in his career. (Coincidentally, Toronto had recently moved Schroder to the bench in the last week.)

Simply put: Quickley can be the Raptors long-term answer at the point guard position.

Quickley is a score-first player, but there are some playmaking chops there that didn’t get a chance to shine in New York. As a scorer, Quickley excels in using screens to create his own looks. He’s a good pullup shooter and he’s got one of the best floaters in the game.

Just as importantly, Quickley is a good off-ball player too. In New York, where the ball is controlled by Jalen Brunson and Julius Randle most of the time, Quickley has learned how to spot-up for jumpers. Or he attacks hard closeouts to get into the paint himself for his floater, or to find a teammate.

That will be important in Toronto too, as Scottie Barnes has become the Raptors main offensive engine. Pascal Siakam will continue to drive the offense a lot too, for however long he’s still there (more on that in a bit). And it’s fair to expect Toronto to let Barrett run the show for some possessions too.

But Quickley is going to get a chance to show what he can do. He’s a major upgrade over Schroder. And his presence should allow Schroder to go back to the bench role where he excels.

On defense, Quickley is competitive against opposing ballhandlers. No pun intended, but he uses his quickness to stay in front of them, and to challenge for steals. Like most smaller guards, Quickley can get overwhelmed inside against bigger players. Toronto should have enough size on the floor to counter that, however.

One bonus with Quickley: He’s a very good rebounder for his size. He’s terrific at snagging a defensive board and triggering transition offense by himself. Look for that to be something that Toronto emphasizes.

Long-term, Barrett is in the fold for next several seasons. He’s under contract through 2026-27 with no options. Provided Barrett proves he can fit with Barnes as a forward/wing pairing, the Raptors should be set for a while at that spot. If that pairing doesn’t work, Barrett’s contract isn’t so onerous that he couldn’t be moved as the Raptors continue to find players to maximize Barnes.

Quickley will be a restricted free agent this summer. He reportedly wanted an extension in the range of $25 million AAV, and $100 million overall. That’s fair, but not something the Knicks were likely to do. Locking up that kind of money for Quickley, when Brunson was already in the fold and entrenched as the starting point guard, would have been somewhat questionable for New York.

Toronto doesn’t have those worries. They can give Quickley that type of deal to bring them stability at the point guard position for the next several years. If bidding gets a little higher for Quickley as a restricted free agent, the Raptors can control the process by matching any offer sheet he signs.

As for the rest of this season, there are reports that Toronto will continue to look to trade Pascal Siakam. He’s a pending free agent, and both he and the Raptors had reportedly set a tentative deadline of December 30 to reach an agreement on an extension. If that comes to pass without a new deal, then Toronto could look to move Siakam before risking losing him for nothing this summer.

As of now, there is reportedly no traction on a trade for Siakam, but that could change quickly. Several teams, including the Atlanta Hawks, Indiana Pacers, Sacramento Kings and Golden State Warriors have expressed interest in Siakam over the past two years. If Toronto chooses to move on from Siakam, they’ll have no problem finding a trade partner.

The key will be what kind of deal the Raptors make. Adding Barrett and Quickley in this trade signals the Raptors are resetting, not rebuilding. Expect a similar type of return for Siakam, in terms of players who can play now.

Assume Toronto will also explore the trade market for Gary Trent Jr., as he’s likely to return to a bench role after this deal. Trent, like Siakam, is set for unrestricted free agency this summer. He’s also extension-eligible, but nothing seems to be moving forward in that area.

Toronto also has over $14 million in expiring salary for Otto Porter Jr. and Thaddeus Young, which would go a long way towards matching contracts in trades. Both are players to keep an eye on ahead of the February 8 trade deadline. As it stands, Toronto is about $2 million under the luxury tax line now. That’s tight, but they should have enough room to make moves, if they want to take on a bit more money.

The Raptors also acquired what looks like it will be the best second-round pick in the 2024 NBA Draft in this trade, as they are getting the Detroit Pistons 2024 second-round pick via the Knicks. That pick projects to be the 31st pick, as the Pistons remain mired in a record-setting losing streak as of this writing. That’s a great value for pick for Toronto to have, whether they use it themselves or dangle it in trade talks.

Long-term, the Raptors took on over $100 million in this trade. That figure is likely to jump to over $200 million, once they re-sign Quickley. But the franchise now has a sense of stability with those two in the fold. If they extend Siakam and/or Trent, that stability only increases. If they trade either Siakam or Trent, they’ll have fully reset both the team on the floor and the cap sheet.

Mostly, Toronto now has a sense of optionality that didn’t exist prior to this trade. They can go in a lot of different directions, and it feels like Masai Ujiri might just be getting started in reshaping the Raptors.