Raptors focused on re-signing VanVleet and Poeltl but challenges remain

TORONTO — The first meaningful few weeks of the off-season went nicely for the Toronto Raptors.

The hard part is just getting started.

The positives?

They announced the hiring of a new head coach, Darko Rajakovic, who immediately made an effort to connect with most of the returning players he’ll be expecting to work with to positive reviews.

The draft went well with the Raptors managing to acquire a highly regarded prospect in Gradey Dick whose top attributes — the ability to shoot from deep and on the move — should potentially fill gaps on their existing roster.

Things worked out well with Gary Trent Jr., who picked up his $18.5 million option for the 2023-24 season rather than heading into unrestricted free agency. The move saves the Raptors from the possibility of losing a useful young player for no return while maintaining his utility as a trade asset.

Although Trent Jr.’s camp has signalled interest in signing an extension with Toronto, there are no plans for formal discussions as of now and it’s very much considered something in the "we’ll see" category. A year ago — on the heels of massive extensions to the young, shoot first, defend later wings like Tyler Herro ($120 million); Jordan Poole ($120 million) — here seemed like a universe where Trent Jr. could command a four-year deal starting north of $100 million.

Now? That market seems to have cooled off, and the sense is if the Raptors do want to reach an extension with Trent Jr. it will be a little more modest. If they don’t? A career 38 per cent three-point shooter on a reasonable expiring deal shouldn’t be too hard to move for at least some kind of return.

In any case, the decision on Trent Jr. has been kicked down the road with minimal obligation, and the Raptors keep one of their better shooters under contract at a good price.

Now we get to the hard part: What to do with pending free agents Fred VanVleet and Jakob Poeltl? And where things stand with Pascal Siakam, the team’s leading scorer, all-star and two-time all-NBA selection, who is heading into the last year of his deal and eligible for an extension before hitting free agency in the summer of 2024?

Multiple teams have inquired about the possibility of Siakam being available — Atlanta, Charlotte, Dallas, Houston, New Orleans and Sacramento have made calls — and while few conversations have even qualified as preliminary, it’s not as if the Raptors have been opposed to listening. As has been typical, their true intentions are hard to read: “Not the easiest team to figure out,” said one league source.

Watching carefully, doubtless, will be O.G. Anunoby, the Raptors' all-NBA defender and likely a very popular free agent this time next year, given he should be in line for a deal more than the highest extension Toronto could offer, which would be about $116 million over four years.

It’s a lot of question marks for a team coming off a 41-41 season that cost head coach Nick Nurse his job.

The first order of business is reaching deals with VanVleet and Poeltl. There isn’t much wiggle room here: The Raptors traded away a lightly protected first-round pick to add Poeltl at the trade deadline, confident he was the piece that could help stabilize their lineup. Failing to sign him would be a significant miscalculation. Similarly, Toronto opted not to trade VanVleet at the deadline and would stand to lose him for nothing if he walks in free agency.

The Raptors are expected to meet VanVleet in Los Angeles on Friday night while plans to connect with Poeltl are being ironed out.

Their belief in Poeltl’s on-court value was more or less proven out: Toronto went 15-10 in 25 games with the big Austrian starting, and Poeltl contributed 13.4 points, 9.3 rebounds, 2.2 assists, 1.4 blocks and 1.2 assists on 64.9 per cent shooting in 27.9 minutes a game, while playing excellent defence. It’s hard to get more efficient than that.

Toronto believes returning all or most of their core along with a coaching change could see them be a factor in the East.

Poeltl’s return at the right deal has generally been considered a given with the working assumption that a four-year deal worth something around $80 million would do the trick but things can happen and there are few discounts offered in the NBA. Multiple league sources have said the San Antonio Spurs have inquired about the possibility of a reunion with Poeltl as a veteran centre alongside No. 1 pick Victor Wembanyama, who they project as a stretch four, at least on offence.

After several years of rebuilding in San Antonio, Poeltl made clear last season how much he enjoyed playing on a competitive team again. Are the Raptors his best option, or only one? With Wembanyama in the fold, the Spurs could make a jump. “Free agency can get a little crazy and unpredictable,” as one source put it. “I don’t think Poeltl’s [deal] is as done as people think.”

That leads us to VanVleet, the seven-year Raptors veteran and former all-star who struggled through a rough start to finish up another excellent all-around season as the Raptors' only experienced point guard.

From the moment that it was announced as breaking news in the buildup to the NBA Finals broadcast that VanVleet — as had long been expected — was declining his $22.8 option for the 2023-24 season to test free agency, it’s been clear VanVleet was going to push his market to the limit.

For most of last season — and especially in the wake of VanVleet shelving the possibility of signing a four-year extension for $114 million — the understanding was that he was seeking a deal with an average value of $30 million over three or four years, with three years and $90 million the most likely landing spot.

But all it takes is one bidder to upset a carefully laid plan and the Houston Rockets — who are pivoting from throwing all their eggs in the James Harden basket, per sources — could be that bidder.

One league source told me the Rockets, armed with $60 million in cap room and no state tax in Texas, are going to tempt VanVleet with a two-year deal for $80 million adding veteran stability to a roster teeming with talented players on rookie contracts.

Canadian Dillon Brooks is another Rockets target as is Milwaukee Bucks centre Brook Lopez, according to sources.

“Everyone outside the [Raptors] seem to say VanVleet is leaving,” said one league source. “But if you’re an agent, that’s what you want everyone to say.”

Another source with knowledge of the situation in Houston suggested the possibility of the Rockets’ signing Lopez is overblown  — “not happening,” they said, and the notion of a $40 million offer for VanVleet has yet to materialize, though the Rockets' interest in the Raptors point guard is very much real.

For their part, the Raptors have remained confident they can reach an agreement with VanVleet and feel he wants to remain in Toronto as well, but they aren’t in a position to match a $40 million offer.

"They might have a glass ceiling on the upper end of what they’re willing to pay,” said one source.

As outlined above, going over $30 million for VanVleet would complicate their efforts to sign Poeltl and likely require additional roster moves to remain under the $165 million luxury tax line. As it stands, the Raptors believe they have just enough room to sign their incumbent starting guard and centre to deals in their projected salary ranges with only some minor pruning done to remain under the punitive tax threshold.

But another looming issue is where Siakam stands and vice versa. On the surface, the news that came out on draft night that Siakam only wants to sign an extension in Toronto would seem like a good thing for an organization that has at times struggled to attract free agents or keep their own key players. His first meeting and dinner with Rajakovic in Florida last week went well.

But another way to interpret the message about only wanting to sign an extension in Toronto is that Siakam’s camp is concerned the Raptors are giving serious thought to trading the two-time all-star or at least listening to proposals. Letting the league know Siakam wouldn’t consider signing an extension with a team trading for him and would instead test free agency in 2024 is as much an effort to control their own destiny as a statement of loyalty.

Whatever the intent, it was noted by the Raptors front office, as was the timing of it.

“If you read the tea leaves, it looks like there’s an issue there,” said one league source.

There is plenty of time to work through whatever issues need to be discussed — and a four-year contract extension worth in the neighbourhood of $195 million should help smooth things over.

For now, there are questions.

Would the Raptors deal Siakam to create more room to sign Poeltl and VanVleet, and not have to worry about making a significant commitment to Anunoby the following summer?

Would acquiring teams see through Siakam’s messaging, confident that few — if any — players would reject an offer worth nearly $200 million?

And how do each of Poeltl, VanVleet, Anunoby and Siakam view the roster questions and uncertainty that has been a feature of the Raptors' existence ever since the middle of last season?

How this all pans out in the next few days remains to be seen. As always, some version of the status quo remains a safe bet, but not necessarily a sure one.