How Webster’s past trade deadlines can help predict Raptors’ plans

This may be Bobby Webster’s first season autonomously leading the Toronto Raptors‘ basketball operations, but it’s his ninth as the team’s general manager. Navigating the NBA trade deadline is nothing new to him.

During Webster’s eight-season tenure under former president Masai Ujiri, the Raptors operated as ostensible buyers in four of them. Now, with the team having already equalled its win total from last season ahead of the all-star break — sitting fourth in the Eastern Conference with a 30-21 record — they’re positioned to buy for a fifth time, now with Webster at the helm.

Given that he’s been an integral part of the decision-making process, and that much of the front office remains intact aside from Ujiri (Dan Tolzman has been the assistant GM for as long as Webster’s term), it stands to reason they could follow a similar pattern of behaviour to past deadlines.

Still, this comes with the caveat that with a new lead decision-maker in place, there could also be a departure from previous norms.

Let’s look at how Webster and the Raptors’ front office have previously behaved in similar situations to get an idea of how they might proceed ahead of the 3 p.m. ET deadline on Feb. 5.  

A measured approach is the standard

In three of the four deadlines when Webster and the Raptors were considered buyers, they ultimately completed one trade. In one instance, the 2018-19 championship season, they completed two.

While they’ve been measured relative to the league — not making any splashy moves for big-time stars — the Raptors have still been willing to give up valuable assets to add where they see fit. They traded first-round picks at consecutive deadlines in 2022 and 2023 for Thaddeus Young and Jakob Poeltl when they needed to add rotational depth and a big, respectively.

The 2018-19 season was an outlier

The most significant deadline deal the Raptors have made with Webster involved is undoubtedly trading for Marc Gasol in 2019. They didn’t give up any firsts, but longtime starting centre and fan favourite Jonas Valanciunas was moved along with a promising young player in Delon Wright and bench-mob member C.J. Miles.

The end result added to the importance of this trade, as Gasol was instrumental in shutting down Joel Embiid and Giannis Antetokounmpo en route to Toronto’s first and only NBA Championship.

Yet the Raptors were also uniquely positioned, having finished top four in the East and securing home-court advantage in the first round of the playoffs for five straight seasons. They were fresh off a first-place finish in the conference and a franchise record in wins. However, they’d failed to break through to the Finals, with a pair of losses in the first round, a pair of losses in the second and one trip to the Conference Finals.

After trading for Kawhi Leonard, who was soon to be an unrestricted free agent, and firing reigning Coach of the Year Dwane Casey, the Raptors were all in. This was also the only season in franchise history in which the Raptors exceeded the luxury tax threshold.

The Raptors have traded regrettable draft picks

When the Raptors swapped Goran Dragic and a first for Young and a second at the 2022 deadline, they effectively traded back 13 places in that draft, from the 20th to the 33rd overall pick.

The two players each team selected weren’t of particular consequence; Malachi Branham and Christian Koloko both have tenuous footholds in the league.

But Koloko was taken two picks after the Indiana Pacers selected Canadian Andrew Nembhard. A bona fide starting guard on a Finals-calibre team who is among the best point-of-attack defenders in the sport.

This presents a false dilemma, as there’s no guarantee the Raptors would have drafted Nembhard had they not traded back. Still, it lives on as a “what if?”. 

As does the 2023 first-rounder they also traded to the Spurs, as the Raptors missed out on the opportunity to select from a bevy of talent, including another Canadian in Zach Edey, along with Matas Buzelis and Kel’el Ware.

While it isn’t exclusive to deadlines when the Raptors have been buyers, the front office with Webster as GM has had a tendency to exercise “pre-agency” as a tactic.

Poeltl, Young and Brandon Ingram were all acquired in-season while on expiring deals and signed extensions to remain north of the border in the following months.

Toronto is often perceived as an undesirable destination for free agents. This idea is backed up by the Raptors’ failure to sign big names historically. DeMarre Carroll, Cory Joseph and Dennis Schroder remain the largest free-agent contracts signed in franchise history. Sandro Mamukelashvili‘s two-year, $5.3-million (league minimum) deal is already panning out to be among the team’s best.

So, when they’ve had the opportunity to bring talent in-house early, giving them an extended runway to get acclimated to the organization and the city, and the team more time to pitch them on staying, they’ve taken it.

Outlook for the 2026 deadline

If Webster stays true to past form, the 2026 deadline could be anticlimactic.

Sportsnet’s Michael Grange reported that the Raptors are prepared to be patient and that Webster has “had exploratory discussions on a multi-year extension to his current deal with talks expected to pick up after the trade deadline.”

Yet, despite not being buyers last season, the Raptors pounced on the opportunity to acquire Brandon Ingram at a sizeable discount. Adding surplus value is the modus operandi of front offices, so if a good enough deal is there, Webster may break from past behaviour.

While it’s all on the table — a big swing for a star, trading a first-round pick to fulfill a need, or an unsexy move to get the books right — a more conservative approach would align with previous tendencies.