Raptors: 5 best moves Bobby Webster has made as GM in Toronto

Bobby Webster was quickly ascending the NBA ladder when Masai Ujiri made him his first hire as GM of the Toronto Raptors in 2013. It is Ujiri who gets the bulk of the credit for the Raptors’ rise to perennial contender status, but his right-hand man has been there just as long and also has his fingerprints all over some very successful Toronto teams.

Now, with Ujiri’s expiring contract sowing seeds of concern over his future, Webster’s new deal makes him the sure thing in the club’s front office. So long as the 35-year-old sticks around, the organization seems to be in good hands.

While the laid-back Hawaiian doesn’t quite carry the same celebrity profile as his boss, Webster has shown himself to be a smart, knowledgeable basketball mind capable of identifying, developing, and acquiring talent. His top five moves since being promoted to GM in June of 2017 serve as proof of his highly proficient track record.

Toronto Raptors GM Bobby Webster Honorable Mentions

Because of the recency of Webster’s track record, some moves will still need more time to be fully evaluated. For now, however, there are several under-the-radar free agent signings that seem to be paying off nicely to varying degrees.

Stanley Johnson endured a disastrous 2019-20 season after the Raptors opted to take a low-risk flyer on the former lottery pick, but has flashed some elite defensive potential in an increased role this season.

Conversely, Terence Davis II enjoyed a triumphant rookie campaign as an undrafted free agent, albeit once that has been undermined amidst still-pending assault charges stemming from an October arrest in New York City.

Webster also brought in Yuta Watanabe on a two-way contract, with the team currently reaping the benefits of his frenetic energy and occasional three-pointer off the bench. Likewise, sharpshooter Matt Thomas has had his moments in a reserve role, even if his sub-par defense has kept him from fully earning Nick Nurse’s trust.

Toronto Raptors GM Bobby Webster move No. 5: Signing Chris Boucher

Boucher had all of one minute of NBA experience to his name when, after being waived by the Golden State Warriors in the summer of 2018, the Raptors brought him in on an Exhibit 10 deal that was converted to a two-way and then a regular contract. Bringing the toolsy Candian, who won G League Player of the Year, paid dividends for the big-league club.

Boucher’s growth over his first two seasons with the organization was encouraging, but incremental, with Serge Ibaka and Marc Gasol looming large ahead of him on the depth chart. When an opportunity came for an expanded role with Ibaka and Gasol’s departures this season, the Montreal native latched on.

Apart from a cold stretch of late, the 28-year-old has been the team’s most consistent big man and an early Most Improved Player candidate. Between January 8th and 18th, Boucher averaged 20.7 points, 8.8 rebounds and 3.2 blocks in a dominant stretch.

As Boucher continues to grow as a player on both the offensive end defensive ends, Webster’s keen scouting eye will only be more highly-regarded in league circles. If he ends up taking on a great responsibility should Ujiri leave, moves like Boucher show that the franchise is still in good hands.

Toronto Raptors GM Bobby Webster move No. 4: Re-Signing Fred VanVleet

So much of VanVleet’s identity is forged by his “Bet On Yourself” credo. That mentality drove his two-year, $18 million contract extension in 2018, enabling him to cash in big two years later with a four-year, $85 million deal.

For the Raptors, meanwhile, that bridge deal couldn’t have gone any better. Over those two years, VanVleet doubled his scoring and assist numbers while going from valued reserve to key starter and even earning a 2019 Finals MVP vote. His performance against the Golden State Warriors alone validated his contract.

While $85 million is a lot of money to throw at a limited athlete like Fred, it’s hard to take issue with any of the steps that Webster and the rest of the organization have taken with VanVleet, especially considering how well he’s played since his big payday.

VanVleet looks poised to top 20 points per game this season while competing for an All-Star spot. Recently, during a win against the Orlando Magic, VanVleet set a new Raptors record when he dropped 54 points in a game. With or without an All-Star nod, the VanVleet deal is another feather in Webster’s cap.

Toronto Raptors GM Bobby Webster move No. 3: Trading for Marc Gasol

It was easy to like Jonas Valanciunas, but he was no Gasol. The upgrade they got by trading the Lithuanian big man for the long-time Memphis Grizzlies star from both a passing and defensive standpoint was monumental.

Two years later (almost to the day, actually), a clear winner in the deal has been determined. Valanciunas has been fine in Memphis, albeit in two non-playoff seasons. C.J. Miles has played in just 23 games since the deal and is currently out of the league.

Delon Wright has been traded twice since and is now a member of the lowly Detroit Pistons. Unless the 2024 second rounder somehow turns to gold, the Raps didn’t surrender much. On the other hand, Gasol helped stymie the likes of Orlando’s Nikola Vucevic, Philly’s Joel Embiid, Milwaukee’s Brook Lopez, and Golden State’s Draymond Green on the way to the title.

You could certainly make the argument that the 2019 championship – and, ergo, the Spaniard’s MVP-caliber parade celebration – doesn’t happen if Webster doesn’t swing the fateful deadline deal. The Gasol trade goes to show that Webster’s fingerprints are all over that championship-winning team.

Toronto Raptors GM Bobby Webster move No. 2: Hiring Nick Nurse

If we’re being honest here, the 2018 coaching change that saw Dwane Casey kicked out in favor of Nurse was far from popular. After all, while the team’s playoff struggles were a real concern, Casey had just presided over a franchise-record 59-win regular season and would earn NBA Coach of the Year honors six weeks later.

If early playoff exits and a stagnant, uninspiring offensive attack was the problem, then what was an assistant on Casey’s staff going to do about it? Luckily, Webster and Ujiri knew what the rest of us didn’t; that Nurse had a wide array of creative, unconventional ideas that simply weren’t going to mesh with a Casey-led squad.

We’ll never know if Casey would also have won a title coaching Kawhi Leonard, but career seasons from the likes of VanVleet and Ibaka, plus the fact that Toronto remained potent even on “load management” days, highlighted Nurse’s impact.

Of course, Leonard wasn’t there to carry the team to their 2019-20 season. If the championship run was Nurse’s star turn, his follow-up season only confirmed his status as one of the league’s best coaching minds. Though the title defense ended in disappointing fashion with Toronto’s loss in the Eastern semis, it has become clear that Raptors brass had nailed the coaching change.

Toronto Raptors GM Bobby Webster move No. 1: Trading for Kawhi Leonard

There was really no other way this was going to end, was there? Even as DeMar DeRozan and Jakob Poeltl remain members of the San Antonio Spurs while Leonard and Danny Green have long since moved on from Toronto, the permanence of the 2019 title gives this deal a landslide victor.

While in Toronto, Leonard put forth an iconic season for the ages, elevating a pretty good team to a great one, delivering a timeless moment (‘The Shot’) and serving up a string of long-lasting non-sequiturs (‘fun guy’, ‘what it do, baybee’, the Kawhi laugh…). Sure, his decision to bolt in free agency at the first opportunity might slightly temper his legacy, but the eternal nature of the championship will ensure that he lives on in Toronto, even after a mere single season.

Lest anyone forget, the blockbuster deal was a huge risk for the Raptors at the time. They were essentially shipping out a franchise favorite who loved Toronto for an injured one-time star who didn’t. In fact, it was a picture of Leonard with Webster and Ujiri that sent Raptors fans buzzing that their new star had at least arrived in Toronto.

Things would only get better from there. While San Antonio Spurs draftee Keldon Johnson offers some promise as the draft pick acquired in the deal, it’ll take a major star turn by the 21-year-old to give San Antonio any hope that the trade is salvageable.

Looking back, it’s been a pretty successful four-year stretch since Webster was named GM. Not that a successful past guarantees anything for the future, but Raptors fans can trust that Webster is smart, analytically minded and very capable of potentially anchoring the office moving forward.