The ideal Raptors offseason: Charting a new course by trading Pascal Siakam

This is going to be divisive.

When I’ve done this exercise in the past, in which I conduct an ideal Toronto Raptors offseason, the possibilities have felt limited. Maybe there has been a key free agent to re-sign. Maybe there has been a draft pick to be made. Perhaps there have been some alterations along the edges of the core to make. Since Raptors president Masai Ujiri took over in 2013, there has only been this much uncertainty about what comes next once: In 2018, after the Cleveland Cavaliers swept the Raptors for the second year in a row, leading to the firing of the coach and the trading of the team’s leading scorer.

After missing the playoffs this year, the coach is already gone, and everything else, aside from Scottie Barnes’ departure, is on the table. This truly is an “if this, then that” kind of summer. Transactions in the NBA are always interconnected, but they will feel especially so this year.

As a product, this is the longest it has ever taken me to write this, and the most words necessary. Sorry to my editors. What’s worse? If I delved into the deep pool that is two-way players, this would have been even longer.

As a reminder, while this is done from a Raptors’ perspective, every move here has to make more than a modicum of sense for the other parties. I also assumed Fred VanVleet and Gary Trent Jr. will decline their player options and enter unrestricted free agency this summer.

A final note before we get to this: I’m working under the assumption the salary cap will be $134 million and the luxury-tax threshold will be set at $162 million. Due to the Raptors’ position — they can create about $30 million of space under the cap, but only if they renounce the rights to all three of their marquee unrestricted free agents — I am operating as if the Raptors will be an over-the-cap, under-the-tax team, freeing up the use of the non-taxpayer midlevel exception. For more on what this means, old friend Blake Murphy’s Raptors cap primer is an invaluable resource.

More Raptors offseason content: Further Raptors offseason reading: 13 thoughts on the 13th pick | Free agency big board | Raptors trade tiers | Mailbag Part 1, Part 2 | Decoding Masai Ujiri | Nick Nurse’s firing

---

Sometime in the next few weeks: Hire Monty Williams as head coach

Of the big names who became available since the Raptors fired Nurse, Williams is the only guy who makes sense for the Raptors. Doc Rivers was the coach in Orlando when the Magic gave Ujiri his first job in the NBA, as an unpaid international scout. However, Rivers is 61 and has been coaching championship contenders (or franchises clearly building toward that in the near future) every season since 2007-08. That is 16 consecutive seasons! It is an open secret that neither Mike Budenholzer nor the Raptors thought they were a good fit for one another back in 2018 after Dwane Casey’s departure. People change, but not that much.

Williams is 10 years younger than Rivers, and has a history coaching a younger New Orleans team along with the Phoenix Suns (who, mind you, were fairly young themselves, aside from Chris Paul, until the Kevin Durant trade). He has coached several styles, as well. The only real red flag was his deteriorating relationship with Deandre Ayton, a big man who often has shied away from physicality. Barnes comes with concerns, too, but they have little to do with physicality. Williams has generally been a stabilizing force with whom players like working.

If not Williams, I do not think there is a clear front-runner. On Monday our Shams Charania and Joe Vardon reported the Raptors met with former Brooklyn Nets coach and notable Canadian Steve Nash. Becky Hammon has done everything you can do from a coaching perspective except be a head coach in the NBA, but her suspension for comments made about Dearica Hamby’s pregnancy is an earned mark against her, although certainly not disqualifying. (NBA teams have hired men with far more questionable issues from the past​​.) Former Nets coach Kenny Atkinson is known for his expertise in player development, which would be a boon for the Raptors, but how much should the Golden State Warriors’ struggles with their “two-track” plan be held against him? There are any number of other good coaches looking for a shot, and an open mind and synergy with the front office are the only real musts.

With all that said, Williams would be my first choice.

June 22: Trade Pascal Siakam and 13th pick in 2023 NBA Draft to the Portland Trail Blazers for Anfernee Simons, Nassir Little, the third pick in 2023 NBA Draft, first-round pick in 2026 (top-six protected in 2026, top-four protected in 2027, top-one protected in 2028, becomes two second-rounders if not conveyed); trade Simons to the Memphis Grizzlies for Luke Kennard and Tyus Jones

Select Scoot Henderson, 6-foot-2 guard from G League Ignite with third pick

First, the trade, which can only be completed after the Trail Blazers make the pick since they owe a protected first-rounder to Chicago in 2024. I don’t think Barnes is going to develop quickly enough to become a truly complementary player alongside Siakam. Neither shoots well enough at the moment, and neither makes decisions quickly enough, either. The more than seven-year age gap is not insurmountable, but it feels increasingly unlikely to hit for the Raptors in the form of a true title contender. Accordingly, I’m trading Siakam for the pick, which produces a core piece of the future, another pick that protects the Trail Blazers from a disaster scenario and what amounts to depth.

Some people might not like that, and I get it. I know a lot of people would insist on getting Shaedon Sharpe from Portland, or would prefer taking Simons instead of the depth from Memphis. There are moves that could net the Raptors more in present help. However, I am high on Henderson’s ability to be the type of downhill creator the Raptors so badly need in their system, I like all the pieces I’m getting back to make the Raptors competitive this season (and sturdier in the face of injuries), and I don’t think there is a bad contract among the bunch. That is to say, I think I could trade them for more stuff later. This is the start of a roster makeover, not the end of one.

So, would the other teams do this? I’d bet the Trail Blazers would prefer O.G. Anunoby to Siakam. If I had to, I’d probably do a version of this trade (let’s say Anunoby, Chris Boucher and Otto Porter Jr. heading out instead) for Anunoby, and that would certainly alter the draft equity. But this is a perfect Raptors offseason within reason, and Anunoby is the younger player who is easier to fit. Is having an extended Siakam alongside a re-signed Jerami Grant and Damian Lillard for, let’s say, $110 million in 2024-25, with a lot of roster-building work to do, ideal? No. There is a little too much overlap between Siakam and Grant. However, it raises their defensive floor tremendously, allows them to stay in the lottery this year and continue to work with Sharpe. It’s definitely a team that makes more sense around Lillard, if that’s the direction they choose to go.

I’m not opposed to keeping Simons, but I’m not crazy about his player type (smaller, scoring-minded combo guard), even if he is one of my favourite players among that type. Memphis gets some Ja Morant insurance for the short term, and a prolific third guard in the long term. The Raptors get a shooter in Kennard and a veteran point guard to help with Henderson’s growth in Jones.

Yes, Henderson. Frankly, assuming the due diligence with Brandon Miller works out — not something to be skimped over, to say the least — both he and Henderson would be excellent basketball fits alongside Barnes. Miller would be easier in the short term, but the Raptors have enough long wings in the system. Given the choice, which they would not have in this scenario, I’d take Henderson. It would be messy in the short term, but it pays off down the road. But either player would make sense for the Raptors.

June 28: Waive Joe Wieskamp and Thaddeus Young

I swear, I’m not going to use this spot to say anything else about Jeff Dowtin Jr.

Wieskamp’s $1.93 million contract for next year guarantees on June 30, while I have to eat $1 million of Young’s $8 million to get off of it. Again, that must be done before June 30. I need roster spots for other moves, so they get to explore free agency.

June 30: Trade Malachi Flynn to the San Antonio Spurs for 2024 second-round pick (initially owned by Los Angeles Lakers)

With Henderson and Jones in, Flynn is not getting run on this team. The Spurs, who have no point guards under contract, get a cheap look at him in the last year of his rookie deal, and Flynn gets a real shot at minutes. The Raptors get one of the Spurs’ 39 second-round picks back and they get another roster spot.

July 1: Agree to terms with Jakob Poeltl (unrestricted, Bird rights) on four-year, $84.4 million contract, fourth-year team option

Agree to terms with Donte DiVincenzo (unrestricted, midlevel exception) on two-year, $18.45 million contract

Watch as Gary Trent Jr. (unrestricted), who declined his player option, signs elsewhere

This begins the Raptors’ penalty for their activity at the trade deadline. To be clear, the Poeltl trade was fine in a vacuum, and could end up being pretty good value for the Raptors. Poeltl is a quality starter. Now, they have to pay him as such. This contract puts him alongside Myles Turner and Jarrett Allen, ahead of the Mitchell Robinson/Jusuf Nurkić class. That feels fair, especially if league revenue, and therefore the cap, continues to rise. Still, no position is more likely to shift in value than centre, and I’m doing everything I can to stay away from a four-year deal here, even if it means bumping the annual salary up.

The DiVincenzo and Trent moves happen in concert. By trading for another UFA at the deadline, the Raptors made it very difficult on themselves to try to retain all of VanVleet, Trent and Poeltl. Frankly, I’m not sure the Raptors should still want to be in the Trent business, especially if they are going to move away from the aggressive defensive style that gives him most of his utility on that end. You’re likely paying DiVincenzo, who hit 39.7 percent of his 3s with Golden State but is about league average for his career. Hopefully he is closer to his Warriors numbers, although one cannot underestimate the impact of playing next to two of the greatest shooters of all time. He also has some creativity to his game, useful in the secondary creation department.

July 4: Agree to terms with VanVleet (unrestricted, Bird rights) on a four-year, $124.9 million contract, and trade him to the Chicago Bulls for Lonzo Ball, Patrick Williams and a 2026 second-round pick

First of all, if the Raptors do not trade up and get Henderson, I believe they should retain VanVleet. For starters, he is a good player and a good leader. Secondly, I don’t want to lose him for no return.

We’re in a different reality here, though, and the deadline penance continues, to a degree, in the form of the two years left on Lonzo Ball’s contract. It’s possible he might never play again. However, the Bulls have no cap room and an obvious need for an organizer and shooter. The front office said it has no intention to rebuild. If I’m Chicago, I probably wouldn’t do this trade, but I can see the Bulls seeing VanVleet as a good fit with their starters. The cost is Williams, who has one year left on his rookie deal and still hasn’t proven he’s anything more than a solid rotation player, and a pick. VanVleet, who would have to agree to this, gets to go home (or close enough), and play for a team that is trying to be competitive instead of a lesser team with cap money to spend.

For the Raptors, I like Williams. He is another tall forward, but he has shot 41.4 percent on 444 career 3s. That has come at a low volume, but it gives me hope. It also means I am no longer dependent on the inconsistent Precious Achiuwa. He is going to have to earn his minutes.

July 15: Re-sign Dalano Banton (restricted, early Bird rights) to a three-year, $8.1 million deal, with a partially guaranteed second season and a non-guaranteed third season

Along with two-way players Dowtin Jr. and Ron Harper Jr., Banton is a restricted free agent. Banton has not done enough to warrant continuing this experiment, but given his length and versatility, I’d try to sign him to a low-risk deal with team-friendly upside. I think Banton would jump at an NBA guarantee for next season, too.

Oct. 1: Sign Anunoby to a four-year, $117.57 million extension, with a player option in 2027-28

Assuming the reports are correct and teams will be able to extend their eligible veterans under contract for 140 percent of their previous salary versus 120 percent in the prior CBA, this would be the most money the Raptors could offer Anunoby this offseason. In this case, Anunoby declines his player option for 2024-25, and has a starting salary that year of nearly $26.1 million. His player option is worth $19.9 million.

I want Anunoby around. With Siakam and VanVleet gone, he is the lone link to the past, but this contract is fiscally responsible, taking him through his age-29 season, assuming he opts out of the final year. Anunoby is a defensive menace and a good, not great, shooter, a piece that makes sense for any team. If I need to move Anunoby, this contract should be friendly enough to teams.

Would Anunoby forgo unrestricted agency heading into his age-27 season to sign this now? In all likelihood, he would not be maximizing his earnings here. On the other hand, it is a lot of guaranteed money, and the top two usage guys from last year’s team are now gone, leaving a void for Anunoby to try to fill as Barnes and Henderson grow. If I had to guess, I’d say he’d probably turn down the offer, but don’t make me tap the sign that describes this exercise. “Probably” is the keyword. The player option is necessary to get the deal done, and the Raptors have not been averse to including player options before.

Notably, Achiuwa and Patrick Williams would be eligible for rookie extensions in the offseason. I would see if there is anything that can be done on both fronts, but I’m inclined to keep my options open and see which, if either player, blossoms.

The finished product

Here is the depth chart, once again, excluding two-way players.

PG: Henderson, Jones, Banton, Ball (injured)
SG: DiVincenzo, Kennard
SF: Barnes, Little
PF: Anunoby, Williams, Achiuwa, Otto Porter Jr.
C: Poeltl, Christian Koloko, Chris Boucher

I have guaranteed more than $157 million, about $5 million below the projected luxury-tax threshold, to 15 players. The players with fully guaranteed contracts beyond next season: Anunoby, Poeltl, Barnes (once I pick up his fourth-year player option), Henderson, DiVincenzo, Little, Ball and Boucher. They will cost $114.89 million in 2024-25 (not including a light guarantee for Banton), which is unlikely to give me meaningful cap room next offseason, either.

This roster, stylistically, is admittedly a mess. My thinking is that at least it is a younger mess. Sure, the Raptors are out of their 2024 first-rounder, assuming it doesn’t land in the top six, because of the Poeltl trade, but that is a sunk cost. The Raptors shouldn’t be overly concerned about whether the Spurs get the seventh or the 17th pick.

Shooting is an even bigger problem than it was last year. There are no pull-up threats from distance. DiVincenzo, Kennard, Anunoby and Williams are all decent to very good spot-up shooters, but the Raptors are going to need to move the ball well to create those looks. (Good luck, Monty.) A lot of that will be on a rookie, Henderson, and the Raptors will have to absorb the ups and downs that come with that.

This is what picking a lane looks like, to me. First of all, I’m not convinced this team is going to be bad. The fit is not great, but there is real depth here. (I have Henderson, Barnes, Anunoby and Poeltl as the four guaranteed starters, with DiVincenzo and Williams battling for the other spot.) Jones, Kennard, Little, Achiuwa, Boucher, Koloko, maybe Porter and whoever doesn’t earn the other starting spot? That is far more depth than the Raptors had last year. I would have liked to move either Boucher or Porter for a smaller player with some shooting, but there was no obvious one-for-one deal, and I’m not looking to move any more draft picks. The Raptors could look to move Porter to a team with a trade exception for the extra roster spot, but Denver is the team that has one big enough to absorb his contract, and the Nuggets are already over the tax for next season.

Next year’s team probably is in a fight to make the Play-In Tournament and struggles to score, especially down the stretch. My reply: Remember last year’s team? I have similar problems, but I’ve picked up a future core player in Henderson and another future first-rounder, plus a few second-rounders, to contribute to what comes next.

Whether you think this offseason is a success depends mainly on: 1) How much you believe in Barnes; 2) How much you believe in Henderson; 3) Whether you think the two can fit well together in the future. I’m betting two really talented players figure it out, with enough veterans to buy them some time to get there. And if the offence is so bad that it sinks the season? Well, maybe the Raptors keep their pick in 2024, after all.

One guarantee: Things will absolutely not play out like this. The Raptors are in a pickle, and there are any number of variables, from Portland’s draft intentions to trade offers for their veterans to VanVleet’s preferences in free agency, that will shape what happens.

(Top photo: Mark Blinch / Getty Images)