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2023-24 Raptors season: 15 increasingly bold predictions

No more fake picks.

Usually, when writers, my past self included, toss out “bold predictions,” what we’re really doing is coming up with things that could plausibly happen, but we don’t fully believe. In other words, we lean into the “bold” part, not the “prediction” part.

Well, be the change you want to see in the world. Below are 15 things about the upcoming Raptors season I genuinely believe will happen. Some of them are more likely than others to come true, but my conviction in all of them coming true is the same — or close enough.

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The gimmick, then: I am ranking these predictions by how bold I think they are. We start with the prediction I feel is safest and end with the one that feels the least likely to come true.

This is the part where you have to wonder: Wait, is he just doing this because he can’t think of something wild to truly predict? To which I say, enjoy the predictions!

1. The Knicks’ lawsuit against the Raptors will be settled out of court

We might never know the details, but there is no way the NBA allows this to happen in front of prying eyes and eager ears.

2. Gradey Dick will be in and out of rotation

Back in the summertime, I projected Dick would not be in the initial 10-man rotation. Lots of commenters were not pleased with that assessment.

Not to toot my own horn (toot toot), but the preseason has proven I was on to something there. Even with Precious Achiuwa, Christian Koloko and Otto Porter Jr. unavailable for the first three games, Dick was on the fringes of the top 10. He turns 20 in November, badly needs some reps and has to bulk up. He will spend some time with Raptors 905.

A random sampling of players picked in Dick’s range over the last few years shows that limited playing time in a prospect’s rookie year is not unusual.

Rookie stats for picks 12-14

Player

  

Pick (Draft)

  

Team

  

Games

  

Minutes/game

  

Jalen Williams

12 (2022)

Oklahoma City

75

30.3

Jalen Duren

13 (2022)

Detroit

67

24.9

Ochai Agbaji

14 (2022)

Utah

59

20.5

Joshua Primo

12 (2021)

San Antonio

50

19.3

Chris Duarte

13 (2021)

Indiana

55

28

Moses Moody

14 (2021)

Golden State

52

11.7

Tyrese Haliburton

12 (2020)

Sacramento

58

30.1

Kira Lewis Jr.

13 (2020)

New Orleans

54

16.7

Aaron Nesmith

14 (2020)

Boston

46

14.5

P.J. Washington

12 (2019)

Charlotte

58

30.3

Tyler Herro

13 (2019)

Miami

57

27.4

Romeo Langford

14 (2019)

Boston

32

11.6

Assuming he stays healthy, I imagine Dick will play in more games than he does not, simply because of the toll an 82-game season takes on a team. Just don’t pencil him in for 20 minutes a night.

3. A song from Drake’s new album “For All The Dogs” will be involved in the Raptors’ pregame introductions at Scotiabank Arena

As these are the Raptors, they will change their introduction song a minimum of three times during the season. It’s just what happens.

Still, Drake doesn’t release an album on the eve of the season to not play his global ambassador card and make sure a song gets in the ears of 19,800 people every night.

Fans at Scotiabank Arena might be subjected to Drake’s new album. (Vaughn Ridley/NBAE via Getty Images)

4. The Raptors will finish in the 9-10 range of the Play-In Tournament — again

I told you we were starting with the colder takes. Picking a team to finish where they finished last year is not bold. This team will have better vibes than last year’s, mostly because it would be very difficult not to. However, the league’s depth of talent and the nature of the roster (more on that later) will keep them hovering around .500.

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Here are my top-eight finishers in the East, ranked by my certainty they will finish ahead of the Raptors: Celtics, Bucks, Cavaliers, 76ers, Heat, Knicks, Hawks, Pacers.

5. The Raptors will have a bottom-10 offence in points per possession

That offence nobody could stand the last two years? Well, it finished 13th and 15th in the league last year and the year before, respectively. We all know that in the last years under Nick Nurse, the Raptors played the possession game so intensely as to allow for that, but it certainly made the Raptors a more prolific team than they would have been with a less extreme strategy.

The emphasis on ball and player movement under Darko Rajaković is great, which should lead to a more entertaining team to watch on a nightly basis. However, if the Raptors are turning other teams over less often and turning it over more themselves (that is what happens, generally, when you pass more), efficiency will take a hit, barring some massive shooting jumps from several players. As Nurse was fond of saying, a possession in which you don’t get a shot is guaranteed to be worth zero points, and the Raptors will have more of those this year.

6. Javon Freeman-Liberty will be this year’s Jeff Dowtin Jr. (in a good way)

An older guard with decent size on a two-way contract? Yes, JFL will earn fans with his play this year. With the reserve-guard situation as unsettled as ever, Freeman-Liberty, who just turned 24, will have some nice moments with the Raptors.

Freeman-Liberty averaged 14.3 points per game with Windy City of the G League last year, shooting 37.1 percent from 3. He is not a natural point guard, so Malachi Flynn should get the first extended shot at backing up Dennis Schröder. I could see Freeman-Liberty sneaking in there a little earlier than his status would indicate. Of the Raptors’ three two-way players, Freeman-Liberty is the most likely to contribute to the Raptors this year.

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(I don’t anticipate there will be a controversy over his contractual situation, as was the case with Dowtin, though.)

7. The Raptors will have a top-10 defence

In the same way that Rajaković’s schemes might reveal how comparatively little offensive talent the Raptors have, I also think they will shine a light on how good this roster is defensively. Even without making it a priority, the Raptors won’t be able to help but finish in the top 10 in forced turnovers. With Jakob Poeltl serving as a more legitimate rim deterrent than they had prior to the deadline, this team has enough skill and experience to be solid defensively.

After the Poeltl trade, the Raptors ranked seventh in defensive efficiency. That was against a soft schedule, but I believe their play on that end was a fair representation of how good they can be.

8. The Raptors will have no All-Stars or All-NBA players

The possibility of injury replacements makes me a little less sure of the first part, as does the immense talent of Siakam (and Barnes, who could get to the fringes of the conversation this year). Saying that, I expect the Eastern Conference to be very top-heavy this year, with it entirely possible that the top-three teams in the regular season producing up to eight All-Stars.

If you don’t make an All-Star team, it’s difficult to make an All-NBA team at the end of the year — not impossible, but it means you have to have a big second half of the season. Siakam is very durable, so the 65-game minimum might end up working in his favour. Again, the Raptors’ record will work against him as the coaches get to the wild-card spots.

My 12 Eastern Conference All-Stars: Damian Lillard, Trae Young, Giannis Antetokounmpo, Jayson Tatum, Joel Embiid, Tyrese Haliburton, Donovan Mitchell, Jaylen Brown, Evan Mobley, Bam Adebayo, Jalen Brunson, Jrue Holiday.

Eric Koreen expects Pascal Siakam’s contract extention will drag out to the offseason.  (Mark Blinch/Getty Images)

9. Pascal Siakam will not sign a contract extension during the season (but will re-sign with the Raptors in the offseason)

I have little feel for how bold this actually is. If the Raptors and Siakam haven’t agreed on an extension by now, I don’t think it will happen during the season. Siakam might as well go play the season and see if he can make All-NBA, thus qualifying for a supermax deal. As you see above, I don’t think that will happen, but it makes sense for him to see if he can pull it off.

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However, the Raptors will still have the hammer in offseason negotiations. Not only will they be able to offer an extension before free agency, they also have his Bird rights if/when he enters free agency. In other words, they alone will be able to offer him a fifth year on a brand new contract (not an extension), and they alone would be able to offer him eight-percent raises instead of five-percent raises.

I think, ultimately, that will rule the day. It probably should have happened already, but I feel that’s where this ends up. As for the possibility of a trade, sure, that is real. I find it fairly unlikely offers go up for Siakam the closer he gets to free agency. If the Raptors have not agreed to an offer yet, they are planning to err on the side of retaining him.

10. Jakob Poeltl will be in more than the odd trade rumour

This has more to do with the Raptors’ odd positioning — not quite going for it, not quite rebuilding — than anything specifically to do with Poeltl. Saying that, Poeltl just signed a four-year deal, so the assumption would be he will be a Raptor for a while yet.

I would guess he will make it through the season. With that said, there are several plausible contenders who could use starting-calibre big man — Milwaukee and Boston at the highest level, with Oklahoma City, Dallas and the Clippers at a lower level. If the Raptors spin their wheels, turning around and trading Poeltl would be a quick way to recoup some of the draft capital that they have lost over the last few years.

Ultimately he won’t go anywhere this season, which is generally the safe bet, especially in recent years.

11. The Raptors and Gary Trent Jr. will agree to a contract extension

In a vacuum, this makes no sense. Trent is clearly not as big of a contributor as Siakam or O.G. Anunoby, and therefore shouldn’t be as much of a priority.

This is about signability more than anything else. The Raptors cannot currently offer Anunoby as much money as he will get on the open market. Meanwhile, if there was a window to happily agree to a long-term pact with Siakam, I think that moment has passed.

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Meanwhile, the Raptors can offer Trent an extension with a maximum starting salary of nearly $26 million, which is 140 percent of his salary for this season. At the same time, it’s tough to imagine him taking less than the $18.6 million he will make this season. That makes the realistic band relatively small, and the return for Trent in a trade probably wouldn’t be great enough to blow the Raptors away.

We will see what comes of the Buddy Hield situation in Indiana, given he is a similar player to Trent, albeit older. I’m calling a three-year, $78-million extension for Trent with the Raptors: safely under the Tyler Herro/Jordan Poole range, but a legitimate raise.

12. The Raptors’ highest-usage player will have the lowest percentage among his peers across the league

This might sound both obscure and like a bit of a reach, but I can assure you it is more the former than the latter. Last year, Siakam shot a field goal, free throws or turned the ball over on 27 percent of the Raptors’ offensive possessions when he was on the floor. Depending on what your games/minutes-played bar is, only two to five teams had lead players who used a lower percentage of possessions. (Miami and Indiana are the two with no qualifiers. Charlotte, if you exclude the largely injured LaMelo Ball, Detroit, if you exclude the largely injured Cade Cunningham, and Denver, if you exclude the traded Bones Hyland, also came in with top players below Siakam’s threshold.)

Rajaković’s system is likely to make the Raptors even lighter on heliocentrism. I would still predict Siakam to get the highest share of possessions, but it would not shock me if either Trent or Barnes edged him out. Either way, this will likely be one of the more egalitarian offences in the league.

Workers of the world, unite.

13. Scottie Barnes will break the franchise record for most triple-doubles in a season

Yes, a new franchise record! Maybe a little less exciting once you realize that the most triple-doubles by any Raptor in a single season is three, set by Kyle Lowry in 2017-18. Still: franchise record.

Barnes has posted one triple-double in his career. Siakam has five, including two in both of the last two seasons. The playmaking duties will tilt slightly toward Barnes, and assists are probably the hardest one of the three thresholds to reach on any given night.

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Free prediction: The Raptors will sign Barnes to a maximum-level rookie extension in the offseason.

14. The Raptors will trade O.G. Anunoby before the trade deadline

I don’t think the Raptors want to trade Anunoby. He is a great complementary player, young enough to want to keep in Toronto no matter what direction the Raptors take and a brilliant defensive player.

The trade deadline should serve as a moment for the front office to really assess where the Raptors stand, though. If they are where I think they will be — in or around the Play-In portion of the standings — and the league is as competitive as it seems like it will be, Anunoby’s trade value could be massive. Even knowing he will be due for a new contract, the chance to acquire an in-his prime ace defender who would be in any team’s crunchtime five should be attractive for a whole bunch of teams. Bird rights are gaining importance as fewer and fewer teams use cap space, although there should be enough teams with space to make the Raptors worry about their ability to retain Anunoby at a salary that suits their long-term planning.

I’d project the return for Anunoby to be two lightly protected first-round-picks and a rotation-level prospect. With so many players due for a raise, something has got to give with the Raptors’ salary structure. Of course, we thought that last year, too.

15. Markquis Nowell will finish top-3 in assists per game in the G League

He might be pretty high in turnovers, too, but Nowell will be undistilled fun. It is tough to picture him getting a real shot with the Raptors this year; his size probably necessitates a full year of getting used to the athleticism and speed of the professional game.

It took nine assists per game last year to finish in the top three. I imagine Nowell will have the ball in his hands a bunch in Mississauga. It will be a tremendous benefit to the other players down there to have a true point guard doling out opportunities.

End with a G League prediction. Leave ‘em wanting more.

(Top photo of Pascal Siakam, Scottie Barnes, and Gary Trent Jr.: Cole Burston/Getty Images)

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Christie Applegate

Update: 2024-05-01