It was in the words of one team executive, “a good row.” 

The NBA is its own micro-organism with its own timetables and traditions. 

The hours before the ball goes up are the equivalent of a sound check, or a dress rehearsal. On the floor, players go through their pregame routines, coaching staffs huddle off-stage to finalize game plans, go over lineups, make a quick call home and otherwise kill time.

But as it’s all going on – and never more than this time of the season, with the Feb. 9 trade deadline approaching – eyes are watching, taking in everything. Brief meetings are held and intelligence is gathered and traded. 

Most of it takes place in the first row of seats well before the fans arrive. The more NBA types hanging out, the better the row.  

For weeks now the Toronto Raptors have been in the centre of that world, with a roster heavy with the kind of players who could join the rotations of high-end teams and potentially shift a playoff race, and maybe even shift the league’s balance of power. 

On Monday night in Phoenix, you could see the wheels turning. The Golden State Warriors and Chicago Bulls each had senior members of their pro scouting staff on hand. A clip from Arizona Sports made the rounds on social media of Raptors president Masai Ujiri heading down the tunnel in the company of Phoenix Suns general manager James Jones. Suns-Raptors trade scenarios were bolstered.

The Raptors’ director of global scouting, Patrick Engelbrecht, was at the game, along with Ujiri, general manager Bobby Webster and vice-president of basketball operations Therese Resch. It’s unusual that many of the Raptors’ top staff to be in one place at one time. 

Some version of the same scene have played out at all four of the stops on the Raptors’ road trip. It’s not hard to construct deals that would be of interest to Sacramento, Golden State and Portland – all organizations that are on good terms with the Raptors’ front office. A similar scenario will likely unfold again Wednesday night in Salt Lake City as the Raptors visit the Utah Jazz, another team that’s expected to be active at the trade deadline. 

But as the interest builds, internally there is a sense of caution. No one wants to overreact to a season that has, in some ways, unfolded as a worst-case scenario, with injuries, chemistry and bad luck all contributing to a team that has underperformed. 

Even fixing apparent gaps has to be examined carefully. It makes sense the Raptors would benefit from having an experienced big man who can offer a porous half-court defence rim protection. But is using current or future assets to acquire a centre who might not finish games in the small-ball era make sense? 

The flip side is also true: it’s the small-ball era, but two – if not the most dominant – players in the game are Joel Embiid and Nikola Jokic. Does making a run at a gifted young big man with upside such as the Phoenix Suns’ DeAndre Ayton make sense? Should the Raptors zag?

Ayton has his fans in the organization, certainly, but enough to make a big swing? 

In the absence of firm information, rumours, triangulation and educated guesses fill the void. 

In conversations with representatives of different teams, general themes coalesce. 

One of the main themes is that the Raptors likely won’t be able to move forward long-term with all four of their core pieces, defined as Fred VanVleet, Pascal Siakam, O.G. Anunoby and Scottie Barnes. The reasons are financial – paying them all this year or next will put the Raptors on the path to the luxury tax, which is bad business for a team that was out in the first round last year and is idling in 12^th place after 52 games this season.

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Given Barnes is just 21 and on the second year of a rookie deal and – after an uneven follow-up to his rookie-of-the-year debut – is playing at a level that justifies the Raptors declaring him off-limits in trade discussions for Kevin Durant this past summer, the expectation is Barnes will be a Raptor for a long time. 

Which of the other three – VanVleet, Anunoby and Siakam —  ends up moving, and when, is why the Raptors are the focal point of so much discussion at the moment, from league insiders to bar stools to front offices around the league. 

Where does Gary Trent Jr. fit? The Raptors are more than open to keeping the fifth-year guard who fits the role of a floor-spreader and instant offence microwave, and those with knowledge of his thoughts assert that there’s mutual interest of staying in Toronto. Price will be the issue. 

According to league sources, Trent could expect a deal in the $20-million range if he opts out of the last year of his contract, which is set to pay him $18.8 million next season. In other words, the idea of a Jordan Poole or Tyler Herro-like payday – two young scorers with comparable statistical profiles as Trent Jr. who scored extensions with their own teams in the $30-million per season range — may not be readily available in free agency. 

Meanwhile, league sources peg Trent Jr.’s likely trade value at a protected first-round or two good second-round picks, along with a matching salary. From the Raptors’ point of view, the likelihood of improving your team by moving on from a 24-year-old who has proven himself as a quality perimeter shooter is relatively low. If Trent Jr. was determined to leave, or the Raptors didn’t believe they could re-sign him in free agency, the story might be different. 

Which isn’t to say the Raptors won’t trade him or include him in a bigger deal by next Thursday – and his theoretical on-court fit and his status as a client of Klutch Sports, the agency that has so much sway with the Lakers, hasn’t escaped anyone’s notice. It’s just that Toronto doesn’t feel heavy pressure to make a move for fear of losing Trent Jr. for no return as free agency. 

A similar line of thinking informs the discussion around VanVleet, although his on-court value and his status as a culture setter going back to the Raptors championship season makes his case different. The belief is that VanVleet wants to remain a Raptor, though fit and familiarity aside, money is a factor there too. 

“The worst thing that could happen to Fred is to be traded,” said one league insider. “Unless you’re a superstar who is getting the max no matter what, the best way to get paid is by staying with your own team.”

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Still, the Los Angeles Clippers are VanVleet fans and have been watching him closely. The fit with the Lakers is pretty simple too. 

When I asked VanVleet before the team left for its longest road trip in 15 years if he would pack a “go bag” in case a deal happened when he was on the road, his answer was telling: “Nah. You plan for something, it’s going to happen.”

But VanVleet’s decision to leave his long-time agent has raised eyebrows, even if he told me that people are reading too much into the move and that it had been fulminating since last summer. 

VanVleet hasn’t declared who his new agency will be, but industry insiders believe he will sign with Klutch, who – in addition to representing Trent Jr. – also represents Anunoby and Raptors head coach Nick Nurse. VanVleet’s one-time agent, Andy Miller, runs the coaching and executive division for Klutch. “I’m 99.9 per cent sure it will be Klutch,” said one source who is familiar with VanVleet’s situation.

The interpretation is that it’s a sign that VanVleet plans to be aggressive in seeking the best deal and fit for him, but Ujiri and Webster had dealt well with Klutch in the past, they’re not worried on that front. 

The Raptors believe they have the means to re-sign both players, but their resources are finite. And it should be mentioned that the Raptors’ record in properly assessing the market value of their own free agents is very good. Kyle Lowry went looking for deals in free agency twice and ended up returning, just as VanVleet did before signing his current deal. 

As Sportsnet’s Blake Murphy points out in his always-excellent trade deadline primer cap guide, Toronto could probably re-sign both Trent Jr. and VanVleet – depending on what their market value ends up being — and stay under the luxury tax, but just barely. At the moment, the combined ceiling would be $50 million. Moves to get out from money owed to Otto Porter Jr. or Khem Birch would open up more room, as would a deal involving Chris Boucher. 

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All of which explains why Anunoby has been featured so prominently in trade discussions – there is no expectation that the Raptors are ready to move on from Siakam at the moment and, in Anunoby’s case, the sixth-year wing hits all the right notes as a top-end player at a prominent position, on a good contract, with some term remaining (Anunoby doesn’t hit free agency until the summer of 2024) who could be an instant fit on any team with hopes of making a deep playoff push. 

The Raptors understand what they have – big, defensively versatile wings who can shoot don’t grow on trees – but the recent play of Precious Achiuwa, who has emerged as a nightly double-double threat with many of the same defensive attributes as Anunoby at least allows Toronto to contemplate an Anunoby trade that doesn’t leave a gaping crater in their lineup. 

Anunoby is also the player who could likely net the largest return in a combination of draft picks and quality players. The question is, how much? 

It’s widely believed the New York Knicks are the team that is prepared to offer three future first-round picks for Anunoby, but the quality of those picks isn’t exactly high-end: They have picks belonging to Dallas, Washington and Detroit that are top-10 protected, top-14 protected and top-18 protected, respectively. Not nothing, but the best case is one more chance in the Victor Wembanyama lottery than they are projected to have now. Otherwise, a pair of mid-to-late first-round picks aren’t likely to change the Raptors’ trajectory in the short-to-medium term. Teams such as Memphis and New Orleans have more attractive draft capital and better talent to deal. Denver could be a dark horse too. 

Can the Raptors leverage more as teams begin to make their best offers closer to the deadline? 

That’s the game of poker that’s underway.

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