Basketball, Sports

The 25 Best Raptors Trades of All Time

There has been a lot of consternation about the last few major Raptors trades, particularly the Young and Pöltl trades. So I decided to figure out what the best trades in Raptors history are and to see how poorly these two trades rank.

The Top 25 Raptors Trades of All Time

The first way I decided to evaluate the best Raptors trades of all time was by win shares, both regular season and playoffs. But arguably the best trade in Raptors history was nowhere near the best trade, so I decided to add some adjustments for any trade that contributed to the Raptors winning the championships.

The other method I used was Value Over Replacement Player (VORP). This one was a little more in line with own beliefs, after a minor adjustment for championships, so I didn’t have to fix the result as much.

The ranking below is based on the average of those two rankings. The rankings were fairly similar on the very best trades ever but they began to diverge around position 15, with Win Shares favouring Raptors players with longevity (obviously).

25. Respert for Earl – Average Posotion = 30.5

This trade was so momentous that neither player has a photo in their Wikipedia article.

Raptors get: Shawn Respert, SG:

  • 1.7 Win Shares
  • 0.1 VORP

Bucks get: Acie Earl, C:

  • 0.1 Win Shares
  • 0 VORP

On February 20, 1997, the Raptors traded their backup centre for the former 8th overall pick, who had failed to take off for the Bucks.

The Raptors have such an illustrious history in terms of trades that this minor transaction nobody remembers is in the Top 25 of our Win Shares trade rankings. Mercifully, it is not the Top 25 of our VORP rankings. Let us never speak of it again.

t-23. Tucker for Sullinger and picks – Average = 27.5

Raptors get: P.J. Tucker, SG/SF (at the time, now he is a PF and occasional C)

  • 1.3 Win Shares
  • 0.4 VORP
  • 0.2 playoff Win Shares
  • 0 playoff VORP

Suns get:

  • Jared Sullinger, PF – 0 GP
  • 2017 2nd Rounder (Alec Peters):
    • 0.3 Win Shares
    • 0 VORP
  • 2018 2nd Rounder (George King):
    • 0 Win Shares
    • 0 VORP

At the 2017 trade deadline, the Raptors traded PF Jared Sullinger and two 2nd round picks for former Raptor P.J. Tucker.

This one is a bit of a makeup move. The Raptors had signed Sullinger in the off-season after he had failed to earn a new contract with the Celtics, who had drafted him in 2012. Sullinger didn’t work out and even spent some time in the D League.

Tucker, meanwhile, had been drafted by the Raptors in 2006 but failed to make an impression. Famously, Tucker played overseas for five seasons before the Suns brought him back in to the NBA, just after their competitive run ended. By this point, they were ready to move him for picks and a project.

Tucker instantly became a fan favourite in Toronto and appeared to be one of the few Raptors willing to work during yet another defeat at the hands of the Cavaliers. Even though he was only on the team for 34 games, a lot of fans felt like he was exactly the type of player the Raptors needed on the bench. He left in free agency that summer and subsequently became famous for his intangibles and effort.

Sullinger never made the Suns and played two seasons in China before retiring.

Both second round picks barely played for the suns, though Peters fared much better than King.

Got to view this as a win.

t-23. Murray for Stewart – Average = 27.5

Raptors get:

  • Lamond Murray. SF:
    • 0.9 Win Shares
    • 0.2 VORP
  • 2004 2nd Rounder (Albert Miralles) – 0 GP

Cavaliers get:

  • Michael Stewart, C/PF:
    • 0.2 Win Shares
    • -0.3 VORP
  • 2007 1st Rounder (Jared Dudley) – 0 GP for the Cavaliers

On September 25, 2002 the Raptors traded backup big Michael Stewart and their 2007 1st Rounder for Lamond Murray, coming off a career year for the Cavs. Lamond Murray tore a ligament in his foot and the Raptors still won this trade.

The trade should have utterly backfired for the Raptors, and you could argue it still did given that Dudley was still playing as recently as 2021. However, Dudley never played a game for the Cavaliers, as the pick was traded to Charlotte for a backup wing two years later.

As for the guys who did play, Murray was hampered by health problems. He was effective-ish in limited minutes but the Raptors still waived him in 2005. But Stewart was much worse for Cleveland and they traded him only a year and a quarter later in the Ricky Davis trade.

Sure, nobody really won. And you could argue the Raptors lost by giving up a 1st round pick. But at least by our VORP ranking, this is one of the Top 25 Raptors trades of all time. (Well, at least it’s not one of the worst. That’s the standard we’ve got for this part of the list.)

22. Evans for Kapono – Average = 25.5

Raptors get: Reggie Evans, PF:

  • 1.5 Win Shares
  • -0.1 VORP

Sixers get: Jason Kapono, SF/SG:

  • -2.3 Win Shares
  • -0.7 VORP

On September 7, 2007 the Raptors tradd failed marquee free agent signing Jason Kapono, who had failed to earn a starting spot, for the journeyman, nominal PF Evans, whose game was more like that of a centre’s.

Kapono had just led the league in 3P% the previous season, after winning a championship as a role player with Miami in 2006. The hope was that he would do that again on the Raptors. And he did lead the league in 3P% in his first season with the Raptors. But, in similar total minutes (over more games), he took way fewer attempts. And the next season his percentage dropped, a lot, while his attempts were way up, which didn’t work out.

Evans, meanwhile, was known for his blue-collar effort game, seemingly a far cry from Kapono’s.

But though Evans barely played for the Raptors, struggling with injuries and he was allowed to walk in free agency in 2011, he was still more valuable. (He did grab a then-career best 22 rebounds in one game, too.)

Kapono’s percentages continued to drop. Bad numbers on a bad team mean bad advanced metrics. He too was allowed to leave in free agency in 2011 and he was out of the league by 2012.

21. Skinner for Oakley and a pick – Average = 25

Raptors get: Brian Skinner, PF/C – 0 GP for the Raptors

Bulls get:

  • Charles Oakley, PF/C:
    • -0.5 Win Shares
    • -1.1 VORP
  • 2002 2nd Rounder (Jason Jennings) – 0 GP

On July 18, 2001, the Raptors returned aging power forward Charles Oakley to the Bulls, where he had begun his career, for Brian Skinner, who is nearly 13 years younger than Oak.

So you can see the logic, giving up your soon-to-be 38-year-old PF for one in his mid 20s. But it did not work out for the Raptors. But Skinner was traded before he could play a game in a different Ricky Davis trade.

From an asset management standpoint, giving up a 2nd round pick so you can put a guy into a subsequent trade you lose is not great. But this ended up being addition by subtraction as Oakley was not good in his return to Chicago and was allowed to leave in free agency that summer. He wouldn’t get signed until right before the next season and then his career was over, except for a 7 game comeback in 2003-04.

If the subsequent Skinner trade had actually worked, maybe this is a real win for the Raptors, getting off of Oakley. But, as it stands, it’s just on this list because they didn’t lose it.

20. Olajuwon for picks – Average = 23

Raptors get: Hakeem Olajuwon, C:

  • 2.1 Win Shares
  • 0.6 VORP
  • 0.2 playoff Win Shares
  • 0.1 playoff VORP

Rockets get:

  • 2002 1st Rounder (Boštjan Nachbar):
    • 1 Win Share
    • 0 VORP
  • 2002 2nd Rounder (Tito Maddox):
    • 0 Win Shares
    • 0 VORP

On August 2nd, 2001 the Raptors infamously traded two picks for Rockets legend Hakeem Olajuwon at age 38.

So you can tell how seriously to take the first few trades on this list by the fact that this trade, a legendary boondoggle, is on it. However:

Nachbar had a couple of crappy years with the Rockets and then he was included in the Jim Jackson deal to the Nets.

Maddox played 35 total NBA minutes.

So because the Rockets didn’t do well on their picks, Olajuwon’s infamous final season with the Raptors grades out as better. So this is a “win.”

19*. Pöltl for Birch et al. – Average = 21

Raptors get: Jakob Pöltl, C:

  • 3.1 Win Shares to date
  • 1 VORP to date

Spurs get:

  • Khem Birch, C – 0 GP
  • 2023 2nd Rounder (Sidney Cissoko)
  • 2024 1st Rounder (???)
  • 2025 2nd Rounder (???)

As we all know, at the 2023 traded deadline, the Raptors traded their former 1A centre and too many picks for their former backup centre.

At the moment, this trade is a win for the Raptors because Bhirch might be out of the league, two of the picks haven’t conveyed yet, and Cissoko was just drafted.

But if Jak leaves and any of the picks work out, this might be a disaster. We’ll know about the contract soon enough.

t-17. James Johnson for a pick – Average = 17.5

Raptors get: James Johnson, PF/SF:

  • 3.2 Win Shares
  • 1.6 VORP

Bulls get: 2011 1st Rounder (Norris Cole) – 0 GP for the Bulls

At the 2011 trade deadline, the Raptors gave up their first round pick for Johnson, who was in his second year. The Raptors didn’t make the playoffs, but given Johnson’s age it wasn’t the most insane move.

Johnson was a decent player for the Raptors but there was lots of unfulfilled potential, so they moved him and a year and a half later to the Kings. But he established himself as an NBA player on the Raptors averaging career highs across the board. Eventually the Raptors brought him back in free agency in 2014.

The Bulls picked Cole but traded him immediately, at the draft, to the Heat.

t-17. The Bargnani Trade – Average = 17.5

Raptors get:

  • Marcus Camby, C/PF – 0 GP for the Raptors this time around
  • Steve Novak, PF/SF:
    • 1.4 Win Shares
    • 0.5 VORP
    • 0 playoff Win Shares
    • 0 playoff VORP
  • Quentin Richardson, SF/SG – 0 GP for the Raptors
  • 2014 2nd Rounder (Xavier Thames) – 0 GP
  • 2016 1st Rounder (Jakob Pöltl):
    • 7.2 Win Shares
    • 0.7 VORP
    • 0.4 playoff Win Shares
    • 0 playoff VORP
  • 2017 2nd Rounder (Jonah Bolden) – 0 GP for the Raptors

Knicks get: Andrea Bargnani, C/PF:

  • 2.5 Win Shares
  • 0.1 VORP

On July 10, 2013 the Raptors somehow got the Knicks to trade three older players and three picks for former #1 overall Andrea Bargnani.

At the time of the trade, Bargnani was a few seasons removed from his career year and had been dealing with injuries, in addition to his infamous inconsistency. It is still amazing that the Knicks gave up as much as they did. Like many Raptors fans, they were probably intrigued by his potential.

But it didn’t work out as well as it could have, for the Raptors.

Camby and Richardson never played, though given Camby’s age at the time that was no surprise in his case. Both were waived before the season started.

Novak was more valuable for the Raptors than Bargnani was for the Knicks, by VORP, but they traded him a year later for someone who would never play for them.

Drafted 9th overall, Pöltl is currently 3rd in his draft in Win Shares, 7th in VORP and 6th in BPM. Before they traded him to the Spurs (see below), he was a reliable backup centre for the Raptors, as part of the Bench Mob.

So they only got one true rotation player out of the trade, in Pöltl. And, if you overlook Pöltl’s role in bringing Danny Green to Toronto, the trade is not quite as much of a slam dunk as it looked at the time.

Don’t get me wrong, it was still good to get off of Bargnani, and it brought in one of the assets that led to bringing in the player who won Toronto a championship, but only one of those picks hitting is the tiniest disappointment.

16*. Young for Dragic – Average = 15.5

The most controversial Raptors trade since the Lowry sign-and-trade is not as bad as you think.

Raptors get:

  • Drew Eubanks, C/PF – 0 GP for the Raptors
  • Thaddeus Young, PF:
    • 3.1 Win Shares to date
    • 0.9 VORP to date
    • 0.1 playoff Win Shares to date
    • 0.1 playoff VORP to date
  • 2022 2nd Rounder (Christian Koloko):
    • 1.7 Win Shares to date
    • -0.3 VORP to date

Spurs get:

  • Goran Dragic, PG – 0 GP for the Spurs
  • 2022 1st Rounder (Malaki Branham):
    • -0.1 Win Shares to date
    • -1.3 VORP to date

Infamously, at the 2022 trade deadline, the Raptors traded what everyone thought was the best part of the return for Kyle Lowry, and their first round pick, to the Raptors for, um, Thad Young.

Now, I have long been a fan of Thaddeus Young. Young had a long career of being a useful player though he arguably never lived up to his potential. (He is 5th in Win Shares, 14th in WS/48, 10th in BPM and 6th in VORP in his draft class, going 12th overall.) But there were at least two issues with his acquisition: Young’s age and the duplication of skillsets. For the Raptors, he was fine in his first season, less so this last. But the issues remain: he is inconsistent, he duplicates other players’ skill sets, and age is really eating into his abilities.

Of course, the real issue was the pick that went out with the player that fans imagined would somehow be able to bring back an asset.

Dragic was a former lead guard who hadn’t started regularly in a few seasons. He was salary in the Kyle Lowry trade, as the real target was Precious Achiuwa. Dragic wasn’t expected to play a huge role for the Raptors but ended up barely playing. The Spurs waived him and he signed with the Nets.

Fortunately, for the Raptors, so far Banham has not excelled. But, for fans, the opportunity cost is real. After the Finals, I’m sure there are fans fantasizing about the Raptors drafting Christian Braun instead. And, all season long, I’m sure fans have been ruing giving up this pick instead of taking Walker Kessler. But we our metrics don’t incorporate opportunity cost so you’ll have to accept the trade’s position at 16th.

Also fortunately for the Raptors, Koloko appears to be better than Branham so far. Who knows how that will go but, for the moment, viewing the draft as one in which a good player could be gotten with a 2nd rounder seems correct. Though it’s incredibly early, Koloko is currently 13th in Win Shares in his draft class.

So, if opportunity cost is not taken into account, this trade is a win for the Raptors, so far, though that will change if Banham does better. Also, fans will probably never like it.

15*. Trent for Powell – Average = 15

Raptors get:

  • Rodney Hood, SG/SF:
    • 0.1 Win Shares
    • -0.2 VORP
  • Gary Trent Jr., SG/SF:
    • 10.3 Win Shares to date
    • 2.3 VORP to date
    • 0.1 Win Shares to date
    • 0 playoff VORP to date

Trailblazers get: Norman Powell, SG/SF:

  • 3.6 Win Shares
  • 0.5 VORP
  • 0.3 playoff Win Shares
  • 0.1 playoff VORP

At the 2021 trade deadline, the Raptors traded fan favourite Norm “Playoff” Powell (see below) for Gary Trent Jr. I was a big fan of the trade at the time, given their respective ages.

Trent was a 2nd round pick in 2018 who had been traded on draft day to Portland. He had moved from minor role player to essential bench player and occasional starter over the couple of seasons. Trent hasn’t necessarily lived up to his potential, shooting below his 3P% in Portland and not developing defensively like we hoped. He is not the offensive player Powell is in terms of his skillset.

But Powell only played 63 games for the Trailblazers before they sent him to the Clippers, less than a year later. (Infamously, this happened after they extended him.)

So, regardless of whether or not Trent becomes a more well-rounded player while he is on the Raptors, they win this trade given what Portland did with Powell.

13. Patterson, Vásquez et al. for Gay et al. – Average = 14.5

Raptors get:

  • Chuck Hayes, C/PF:
    • 1.5 Win Shares
    • 0.1 VORP
    • 0 playoff Win Shares
    • 0 playoff VORP
  • Patrick Patterson, PF:
    • 16.5 Win Shares
    • 5.4 VORP
    • 1.8 playoff Win Shares
    • 0.9 playoff VORP
  • John Salmons, SG/SF:
    • 1.4 Win Shares
    • 0.1 VORP
    • 0 playoff Win Shares
    • 0 playoff VORP
  • Grevis Vásquez, PG:
    • 5.4 Win Shares
    • 1.2 VORP
    • 0.4 playoff Win Shares
    • -0.1 playoff VORP

Kings get:

  • Quincy Acy, PF/SF:
    • 1.3 Win Shares
    • 0 VORP
  • Rudy Gay, SF/PF:
    • 16.3 Win Shares
    • 6.8 VORP
  • Aaron Gray, C:
    • 0.1 Win Shares
    • -0.2 VORP

On December 9, 2013, less than a year after trading for him, the Raptors traded Rudy Gay and a couple of role players for four players. It is rightly regarded as a franchise-altering trade (as the trade to acquire Gay was sort of viewed, as well).

Gray had signed as a free agent in 2011 but he had lost his starting spot. He only played 33 games for the Kings and then he was out of the league.

Acy was a 2nd round pick in 2012 but hadn’t found much of a role on the Raptors. He only played 56 games for the Kings. They traded him to the Knicks in the summer.

Gay was a star for the Grizzlies, but he was view by many as an “empty calories” player. The trade for him involved trading away long-time starting point guard Jose Calderon and former 13th overall pick Ed Davis. The reason this trade doesn’t come down as more of a win for the Raptors because Gay ended up playing four seasons for the Kings, and he was the leading scorer in his first full season there.

This had been Salmons’ second stint in Sacramento. He was a long way away from those years, when he had found a starting role. After the trade, Salmons didn’t spend much time on the Raptors, and the Raptors made a huge upgrade when they traded him (see below).

Hayes hadn’t started regularly in a few years. On the Raptors, filled in as backup centre for about a season’s worth of game. He was allowed to leave in free agency in 2015 and played only two more NBA games before he retired.

The real target of the trade was Vásquez, who had led the league in total assists in 2012-13. He had been acquired by the Kings that summer. Vásquez became the backup PG for the Raptors for a season and a half. See below for how he left.

Patterson had also been recently acquired by the Kings but had not earned a starting role. He nearly wins this trade for the Raptors on his own despite rarely starting games. That’s the value in playing for a winning team. Patterson played more games for the Raptors than any other team during his NBA career and so racked up the win shares. He was allowed to leave in free agency in 2017.

Though this trade didn’t make the Raptors a contender on its own, it contributed to the team making the playoffs for the first time in six seasons and began the run of 8 playoff appearances in nine years. And two of the pieces acquired in this trade would contribute to future success.

13*. Gasol for Valanciunas et al. – Average = 14.5

Raptors get: Marc Gasol, C:

  • 5.1 Win Shares
  • 1.8 VORP
  • 2.5 playoff Win Shares
  • 1 playoff VORP
  • Championship value: 4th by Win Shares, 3rd in BPM, t-2nd by VORP

Grizzlies get:

  • C.J. Miles, SF/SG:
    • 0.3 Win Shares
    • 0 VORP
  • Jonas Valančiūnas, C:
    • 16.3 Win Shares
    • 4.8 VORP
    • 0.3 playoff Win Shares
    • 0.1 playoff VORP
  • Delon Wright, PG/SG:
    • 2 Win Shares
    • 0.6 VORP
  • 2024 2nd Rounder (???)

Before the 2019 traded deadline, the Raptors traded their long-time starting centre, and two members of the fabled Bench Mob, plus a pick, to the Grizzlies for former DPOY Marc Gasol.

This is the first trade on this list to contribute directly to the championship. It was one I was worried about because, despite being a Marc Gasol fan, I was worried he wasn’t the player he used to be. It turned out he was enough of that player to matter, holding the players he guarded well below their regular season shooting percentages.

If we don’t adjust these ratings for the championship, this trade isn’t on this list because, by total Win Shares and VORP, it’s a win for Memphis, which is obviously stupid. But Memphis got something out of it.

Miles was the Raptors’ big signing in the 2017 off-season. After starting in Utah he had become a useful bench player for both the pre-LeBron Cavs and, especially, the Pacers. His first season with TO had been okay but during this season he was failing to get minutes and the Raptors wanted to move on. That proved a good idea. Miles only played 13 games for Memphis and was traded in the off-season. He would only play 11 more games after that.

Wright was a different story. Drafted 20th overall in 2015, Wright had found himself unable to secure starting minutes but a crucial part of the Bench Mob. (Wright’s draft class rankings: 9th in Win Shares, 8th in WS/48, 3rd!! in BPM and 5th in VORP. Being a bench player on good teams helps your advanced stats a lot.) Wright played twice as many games but was also traded in the off-season, in a sign-and-trade.

Valanciunas was the Raptors’ 5th overall pick in 2011, and their highest pick between the infamous 2006 draft the present (and Scottie Barnes). I remember the fears of drafting another soft European centre. But Valanciunas was anything but. And there was his performance in the 2016 playoffs when he was arguably the best player on the team before he got hurt. But Valanciunas has never been good defensively and that was perhaps the Raptors’ biggest issue (among many) every time they lost to Cleveland. So it was time for an upgrade.

And that upgrade was a former DPOY (in 2013), as well as 1st Team All NBA in 2015 and 2nd team the year in he won DPOY. At least in terms of pedigree, Gasol was the best centre the Raptors had acquired since Olajuwon.

But the reason why this trade isn’t a win due to regular season stats is solely due to JV. Valanciunas replaced Gasol as the Grizzlies’ starting centre and spent three seasons there before he was traded Pelicans. Though he continued to struggle defending in space, he was also his usual productive self on the offensive end.

After the championship, Gasol had one more year in Toronto, where he was worse, and he left as a free agent in 2020, finishing his NBA career with the Lakers. Given Gasol’s importance to the championship team, this trade still seems like a no-brainer.


t-11. Amir Johnson for Delfino – Average = 11.5

Raptors get:

  • Amir Johnson, PF/C:
    • 32.8 Win Shares
    • 6.4 VORP
    • 0.8 playoff Win Shares
    • 0.2 playoff VORP
  • Sonny Weems, SG/SF:
    • 0.9 Win Shares
    • -0.9 VORP

Bucks get:

  • Carlos Delfino, SF/SG:
    • 10.7 Win Shares
    • 4.2 VORP
    • 0 playoff Win Shares
    • 0.1 playoff VORP
  • Roko Ukić, PG
    • 0.2 Win Shares
    • -0.6 VORP

On August 18, 2009 the Raptors traded hold-out backup shooting guard Carlos Delfino and a former second round pick, averaging 12 minutes a game, for a player who would eventually become their starting power forward and another player. By Win Shares, this is a Top 10 trade in Raptors history but VORP likes Delfino more than Win Shares so it’s just outside the Top 10 on this list.

Ukić was drafted 41st overall in 2005. 2008-09 was his first NBA season, where he average 12 minutes a game on a non-playoff team. After the trade, he lived up to the hype and played 13 more NBA games, all for the Bucks.

Delfino received a massive contract from a Russian team in 2008 and so left the NBA. But Delfino had a decent three years for the Bucks, as their starting SG, at least when he was healthy. They took the Joe Johnson Hawks to seven games one year. He left in free agency in 2012.

Weems was a good enough backup SG/SF that he was out of the NBA by 2011. He played far more games for the Raptors than anyone else, but that is probably more a testament to how bad the Raptors were around the time Bosh left. Weems had a brief comeback in 2015.

But Johnson, who like Weems, never played a game for the Bucks, resurrected his career in Toronto. He had never really gotten a regular role in Detroit but in Toronto e moved progressively from a reliable backup big to the starting PF, as the team also improved. He stuck around long enough for the first couple playoff appearances, where the Raptors got eliminated in the first round. He was allowed to leave in free agency in 2015.

t-11. Clark et al. for Willis et al. – Average = 11.5

Raptors get:

  • Keon Clark, C/PF:
    • 8.6 Win Shares
    • 1.4 VORP
    • 0.6 playoff Win Shares
    • 0.1 playoff VORP
  • Tracy Murray, SF:
    • 1.4 Win Shares
    • 0.2 VORP
    • -0.1 playoff Win Shares
    • 0 playoff VORP
  • Mamadou N’Diaye, C:
    • 0.8 Win Shares
    • -0.1 VORP

Nuggets get:

  • Garth Joseph, C:
    • -0.1 Win Shares
    • -0.1 VORP
  • Aleksander Radojević, C – 0 GP for the Nuggets
  • Kevin Willis, PF/C:
    • 1.4 Win Shares
    • -0.4 VORP
  • 2001 2nd Rounder (Ousmane Cisse) – 0 GP

On January 12, 2001, with the team looking at their second ever (and second consecutive) playoff appearance, the Raptors traded the ghost of Kevin Willis, and two other centres, for the former 13th pick in the draft, NBA journeyman Tracy Murray, and the former 26th pick in the draft. This is the kind of trade that feels like like belongs in another era two bigs and another player for three bigs. Funny trade.

Radojević, the 12th pick in the 1999 draft, had only played 24 minutes of NBA basketball before this trade. I guess the Nuggets thought they could turn him into an NBA players but it didn’t work and he didn’t play another NBA game until 2004, for the Jazz.

Joseph was a free agent the Raptors had already waived once this season. Four years after graduating college, he was still raw, and he played a total of four NBA games, 2 for the Raptors and 2 for the Nuggets. He remains the only Dominiquais NBAer ever.

Willis had just turned 39 and was showing his age in a backup role for the Raptors. The Nuggets were looking for a veteran to backup Antonio McDyess on their push to make the playoffs. It didn’t work out. Willis would be traded only 9 months later to the Bucks. But he wasn’t done, as he would win a championship with the Spurs in 2003. Somehow, he would keep playing through the 2004-05 season and he would make a 5-game comeback in his age-44 season in 200-07. But the Nuggets didn’t really benefit.

N’Diaye was a project and Raptors tried for three years. When the contract expired he signed a few 10 Days but was out of the league by 2005.

Tracy Murray, cousin of Lamond, had once had his best career season for the Raptors but the same thing didn’t happen this time around. On a much better team, Murray had less of a role. His minutes in his first playoff with Toronto were nearly nonexistent and he wasn’t played in the second. He was traded during the 2002 off-season.

Clark came in as a backup but got off to a pretty good start, for example recording 12 blocks in a game that March. His role gradually increased and he found himself starting in the playoffs in 2002 for the Carter-less Raptors. He was allowed to leave in free agency in 2002.

10. Davis for Bender – Average = 10.5

Raptors get: Antonio Davis, PF:

  • 22.8 Win Shares
  • 1.1 VORP
  • 2.5 playoff Win Shares
  • 0.7 playoff VORP

Pacers get: Jonathan Bender, SF:

  • 3.8 Win Shares
  • -0.4 VORP
  • 0.5 playoff Win Shares
  • 0.2 playoff VORP

On August 1, 1999, a month after picking him 5th overall, the Raptors traded high school prospect Jonathan Bender for the Pacers now former starting power forward Antonio Davis. On paper, it looks bad. But I honestly thought it was going to be higher up on this list, given how badly it worked out for the Pacers.

Bender was an extremely tall high school shooting guard who NBA teams imagined being unguardable due to his height. The Raptors took him immediately ahead of Wally Szczerbiak, Rip Hamilton, Andre Miller, Shawn Marion and Jason Terry. (If you’re counting, that’s a borderline Hall of Famer, two other all stars and two other borderline all stars.) Given how some high school prospects were starting to turn out, this was not seen as crazy at the time.

Davis was a former 2nd round pick who had earned a starting spot on the Pacers after playing in Europe but he was starting to lose his spot to the younger Al Harrington.

Again, on paper, seems like an obvious win for the Pacers.

But Bender became one of the poster children to the “too much, too soon” prep-to-pro generation. Injuries limited him to less than 250 games with the Pacers but he also never scored more than 7.5 PPG.

Davis, on the other hand, became, at times, the second best player on the Carter-era Raptors, famously leading the team to a playoff spot when Vince was injured during the 2001-02 season.

The deal in which the Raptors gave up Antonio Davis is higher up on this list.

9. Williams for Salmons – Average = 10

Raptors get:

  • Lou Williams, PG/SG:
    • 6.6 Win Shares
    • 2.3 VORP
    • -0.1 playoff Win Shares
    • 0 playoff VORP
  • Lucas Nogueira, C:
    • 6 Win Shares
    • 1.9 VORP
    • 0 playoff Win Shares
    • -0.1 playoff VORP

Hawks get: John Salmons, SG/SF – 0 GP for the Hawks

On June 29, 2014, the Raptors traded Salmons, who they had acquired in the Rudy Gay trade (above) only 6 months earlier, for Lou Williams and the 16th pick in the previous year’s draft, who had yet to play a game in the NBA.

This is one of those trades that might have made sense for financial reasons for the Hawks but was just disastrous on the basektball front.

Nogueira had been acquired at the draft the previous year but they had never managed to play him. He eventually became the third-string/backup centre for the Raptors, a playoff team, so it’s a little weird the Hawks never even tried to play him.

Everyone knew Williams’ flaws by this point, a decade into his career, and perhaps he had become superfluous to the Hawks with Schröder coming over. But he did his thing during his one season with the Raptors and had one of the best seasons of his long career. Williams left in free agency in 2015.

This seems a lot to give up for a player you waived. It also makes the Rudy Gay trade even better.

8. Rose et al. for Davis et al. – Average = 9

Raptors get:

  • Lonny Baxter, PF/C:
    • 1 Win Shares
    • -0.1 VORP
  • Donyell Marshall, PF/SF:
    • 15.8 Win Shares
    • 6.3 VORP
  • Jalen Rose, SF/SG:
    • 7.2 Win Shares
    • 0.7 VORP

Bulls get:

  • Antonio Davis, PF/C:
    • 6.8 Win Shares
    • 1.1 VORP
    • 0.3 playoff Win Shares
    • 0 playoff VORP
  • Chris Jefferies, SF/SG:
    • 0 Win Shares
    • -0.2 VORP
  • Jerome Williams, PF/SF:
    • 3.3 Win Shares
    • 0.9 VORP

On December 1, 2003 the Raptors traded Antonio Davis, from our 10th best Raptors trade of all time, and fan favourite Jerome Williams to the Bulls for three players, the marquee of which was Jalen Rose.

The Raptors had acquired Jefferies in the Lindsey Hunter trade but he had seen his minutes decline every season since his acquisition. He didn’t play much for the Bulls and was out of the league at the end of the seasons.

Williams had earned the eternal love of Raptors fans for his hardworking style since the Raptors acquired him from the Pistons in 2001 (just in time for the first ever Raptors “playoff run”). Moving him was not popular. After the trade, Williams had a decent rest of the season for the Bulls but they put him in a package for 38-year-old Dikembe Mutombo in the off-season for some reason.

With Chris Bosh now on the team, Davis’ role was shrinking. He started for parts of two seasons for the Bulls, but the decline that had begun this season continued and Bulls traded him and Eddy Curry in 2005 for a boatload of players and picks (a couple of whom became stars).

Baxter was the Bulls’ second round pick on 2002, who had been filling a bench role for them. The Raptors waived him 3 months later.

Rose starred on a bad Raptors team but saw his scoring and role decline as he got older. Weirdly, he was traded for Antonio Davis’ ghost just over two years after initial trade. Surprisingly, that trade did not work out for the Raptors.

This trade is higher up on this list than I imagined and that’s because the advanced stats just love Marshall. According to both Win Shares and VORP, Marshall was never better than when he was on the Raptors, both as a starter and on the bench. (Though, on a per minute basis, Marshall’s brief time in Philly was better, the advanced stats mostly think this was the best part of Marshall’s career.) Sure, Marshall hit 12 3s in a game that one time, but was he really this good? If you’re inclined to think these stats favour 3s too much you might think this position is too high. And the Raptors might agree, they allowed him to walk in free agency in 2005, two off-seasons before the Raptors (sort of) figured it out and became a playoff team.

7. Christie for Alexander and Anderson – Average = 7.5

Raptors get:

  • Doug Christie, SG/SF:
    • 21.1 Win Shares
    • 8.3 VORP
    • 0 playoff Win Shares
    • 0 playoff VORP
  • Herb Williams, C/PF:
    • 0 Win Shares
    • 0 VORP

Knicks get:

  • Victor Alexander, C – 0 GP for the Knicks
  • Willie Anderson, SG/SF:
    • 0.5 Win Shares
    • -0.1 VORP
    • -0.1 playoff Win Shares
    • 0 playoff VORP

At the 1996 trade deadline, the Raptors traded Victor Alexander, who had never played for them, and Willie Anderson, who they acquired in the expansion draft, for Doug Christie and Herb Williams.

Alexander had been acquired before the Raptors’ first season had begun, in the B.J. Armstrong trade. He played as a backup centre for the Warriors before that. The Knicks waived him and he spent the next five seasons in Europe. He had a brief comeback with Detroit in the 2001-02 season.

The Raptors acquired Anderson from the Spurs in the expansion draft, where he’d lost his job as starting shooting guard in part due to injury problems. He did not pay all that well for the Knicks and left in free agency that summer.

Herb Williams turned 38 two days before this trade. He entered the league long enough ago that his Basketball Reference picture is in black and white. The Knicks had signed him as a free agent in 1992, when he was only 34, and he had been a third string centre for them. The Raptors waived him and, five days later, he returned to the Knicks. (So maybe we should include his final Knicks years as part of the Knicks side of the trade? 0.3 Win Shares and -0.2 VORP in case you’re interested.)

The reason the trade happened at all was Doug Christie. Christie had been drafted in 1992 by the Lakers where he had played 21 minutes a game. In New York, where he had been traded for two second round picks, he played less than 9. Either the Raptors saw something in Christie that these two much better franchises didn’t or Christie just needed to go to a team where he could get some playing time to show what kind of player he was. Because Christie quickly became the Raptors’ starting shooting guard, he started appearing on Steals and SPG leaderboards and he started getting All Defense votes. The Raptors traded him to the Kings in 2000 for Corliss Williamson, a bigger player, probably due to the log-jam on the wing. (Spoiler: that was a big mistake.)

6. Ibaka for Ross and a pick

Raptors get: Serge Ibaka, PF/C

  • 16.4 Win Shares
  • 3.1 VORP
  • 3 playoff Win Shares
  • 1 playoff VORP
  • Championship value: 5th by Win Shares, 9th in BPM, t-6th by VORP

Magic get:

  • Terrence Ross, SG/SF:
    • 10 Win Shares
    • 1.1 VORP
    • 0.2 playoff Win Shares
    • 0.2 playoff VORP
  • 2017 1st Rounder (Anžejs Pasečņiks) – 0 GP for the Magic

At the 2017 trade deadline, the Raptors traded backup small forward, Terrence Ross, plus a 2017 1st to the Magic for former Thunder star Serge Ibaka.

The pick was a swap with protections and ended up being the Clippers pick, meaning the Raptors got to draft O.G. Anunoby. Pasečņiks was traded on draft day to the Sixers for a pick that the Sixers would later get back in the Fultz trade. Eventually he played 28 games for the Wizards, mostly prior to the pandemic. Wikipedia says he played with Wembanyama last season but I cannot verify that. He is currently playing in Spain.

The Raptors had drafted 8th overall in 2012. (Ross is currently the 12th best player in his draft by Win Shares, 13th best by VORP and tied for 18th best by BPM.) Infamously, Ross was only the second Raptor to score 50 points in a game, which he did in 2014. But the Raptors figured they make a defensive upgrade. So Ross ended up as the backup shooting guard for the Magic until he was waived this winter in order to sign with the Suns.

Ibaka had started on the 2012 Thunder that went to the Finals, and led the league in BPG twice, so the Magic likely thought they were getting a different maker. But, despite his scoring increasing, Ibaka had failed improve the team. So, only 8 months after traded three players (including both Oladipo and Sabonis) for Ibaka, they turned around and sent him to the Raptors for a non-starter and a pick. We all know what happened next. After signing an extension with the Raptors (that a lot of people didn’t like at the time), Ibaka cemented his role as the team’s starting 4 but then transitioned to a bench role for the Championship run and he had big games against Philly, Milwaukee and especially Golden State. Ibaka left in free agency in 2020. He played 185 minutes this season.

5. Williams and picks for Billups – Average = 5.5

Raptors get:

  • Željko Rebrača, C – 0 GP for the Raptors
  • Michael Williams, PG:
    • -0.1 Win Shares
    • 0 VORP
  • 1999 1st Rounder (Jonathan Bender) – 0 GP for the Raptors (see above)
  • 2000 1st Rounder (Morris Peterson):
    • 30.5 Win Shares
    • 7.2 VORP
    • 0.7 playoff Win Shares
    • 0.2 playoff VORP

Nuggets get (from the Raptors):

  • Chauncey Billups, PG/SG:
    • 2.4 Win Shares
    • 0.5 VORP
  • Tyson Wheeler, PG:
    • 0.1 Win Shares
    • 0 VORP

On January 1, 1999, as part of a 3-team trade with the Timberwolves, the Raptors traded their former starting shooting guard and their former 1998 2nd round pick to the Nuggets for a centre, a much older point guard and some picks. (The Timberwolves acquired players solely from the Nuggets in the deal.)

This is one of those trades that is a huge win for the Raptors in terms of regular season Win Shares and VORP but is arguably a loss in terms of opportunity cost, as I will get into below.

Wheeler had been drafted 47th overall. (Funnily enough, he is tied for 47th overall in his draft in career Win Shares.) He had not played a game for the Raptors and was likely included as a warm body in case things didn’t go well with Billups.

Billups was in the middle of his long journey from potential draft bust to future Finals MVP. Drafted 3rd overall in 1997 by the Celtics, Billups had been traded to the Raptors only 51 games into his NBA career due to Rick Pitino. Billups had started (in a two-PG lineup) for the Raptors for the rest of the season but had then failed to make the team in the 1998-99 season. I was not a serious fan of the Raptors yet, so I don’t know why this happened, but Alvin Williams was the PG and Billups didn’t play.

But it didn’t go well with Billups in Denver (this time). He played shooting guard but lost his starting spot the next season and, just over a year later, was traded to the Magic.

Rebrača, a former 2nd round pick who had yet to play in the NBA, never played for the Raptors. They would trad him to the Pistons in 2001 and he would finally play some NBA games.

Williams was in his age-31 season and had won a Championship as Isiah Thomas’ backup in 1989. (He is also the record holder for most consecutive free throws made.) But he had missed an entire season due to injury only a year earlier. The plan to make him Alvin’s backup didn’t work out and played 2 total games for the Raptors before retiring.

We already covered what happened with the pick that became Jonathan Bender above. A real win for the Raptors.

But the other pick ended up being even more of a win, at least in terms of franchise longevity. The Raptors ended up drafting Mo-Pete, who played over 500 games for the team and had some iconic moments. By Win shares he grades out as the 6th best player in his draft, by VORP the 7th, and he is tied for 9th in BPM. The Raptors drafted him 27th overall so he is one of their early big draft successes. He was allowed to leave in free agency in 2007, when he was the franchise leader in games played.

Of course the opportunity cost here was real and, in a little bit, we’ll cover what the Raptors potentially lost with this (and some other) trades.

But before we get to that…

4. Carter for Jamison – Average = 4.5

Raptors get:

  • Vince Carter, SG/SF:
    • 47.7 Win Shares
    • 26.1 VORP
    • 2.3 playoff Win Shares
    • 1.4 playoff VORP
  • cash

Warriors get: Antawn Jamison, PF/SF:

  • 25.2 Win Shares
  • 7 VORP

At the 1998 draft, the Raptors traded their 4th pick, Antawn Jamison, for his teammate and the 5th pick, Vince Carter, plus some money. I actually was surprised this wasn’t higher. Without an adjustment for the championship, it’s the second best trade in Raptors history by VORP.

Famously, these two played together at UNC and Jamison was considered the slightly better NBA prospect due to his size. But, though Jamison had a great career, he’s one of those guys who has the totals to get in the Hall of Fame but is classic Hall of Pretty Good – great career numbers, never one of the best players in the league. More importantly for this trade, he played only 5 seasons for the Warriors, and they traded him to the Mavericks in 2003.

Meanwhile, it’s hard to imagine the popularity of basketball in Canada at this point in time without Vince Carter. Just look at what happened with Canadian NBAers, once Vinsanity happened, Canada started producing NBA prospects. In addition, he was the greatest player in franchise history until quite recently. (You can get into quite a debate with people about who the Greatest Raptor of All Time is, now.)

No matter how you feel about how Carter left – and it’s worth knowing both sides of that story if you’re still butthurt about it 20 years later – he was the best player in Raptors history for most of the franchise’s existence. And you do this trade 100 times out of 100.

Oh, and in case you care, here are their draft class rankings:


  • 3rd in Win Shares
  • 5th in BPM
  • 3rd in VORP


  • 5th in Win Shares (37.5 behind Carter)
  • 10th in BPM
  • 5th in VORP (only 42% of Carter’s total)

The Raptors Super Team That Never Was

I want to stop here for a moment to consider an alternate history of the Raptors, in which they potentially contend for a championship in the early aughts with players they acquired through the draft and trades, but whom they traded away over the course of what now looks like a very short-sighted period in franchise history.

Consider this starting line-up. (Click on the link.)

I understand this is the kind of thing that belongs in a post about bad Raptors grades but I may not write that one. Anyway, back to our list:

3*. Powell and a pick for Vasquez – Average = 3

Raptors get:

  • Norman Powell, SG/SF:
    • 15.2 Win Shares
    • 3.6 VORP
    • 2 playoff Win Shares
    • 0.6 playoff VORP
    • Championship value: t-7th in Win Shares, 7th in BPM and t-6th in VORP
  • 2017 1st Rounder (O.G. Anunoby):
    • 22.2 Win Shares to date
    • 5.8 VORP to date
    • 1.6 playoff Win Shares to date
    • 0.6 playoff VORP to date
    • No Championship bonus as he didn’t play

Bucks get: Greivis Vásquez, PG:

  • -0.3 Win Shares
  • -0.5 VORP

At the 2015 draft, the Raptors traded backup PG and playoff hero Greivis Vásquez (see above) for the player the Bucks had just drafted at 46th and a 2017 1st round pick. It is one of the great trades in Raptors history – even without adjusting for the Championship it is the 2nd (WS) or 3rd (VORP) best trade in franchise history.

And that’s because the Raptors picked exactly the right time to get off of Vásquez, who was a popular Raptor and the kind of guy fans felt like the Raptors needed more of. He had surgery partway through his season with Milwaukee and, as a result, they let him walk in free agency. He played a total of 26 NBA games after this trade, mostly for the Bucks, after seeming like an indispensable part of the Raptors’ bench. Raptors management has never guessed better about when to give up on a player.

Powell became an indispensable part of the Raptors bench, too, and a reliable spot starter. And though he teased with his potential to be something more, he became known for his big playoff games, a tradition he has continued for the Blazers and Clippers. (He actually averages less in the playoffs but humans love outlier bias.)

Obviously this trade is a win if the Raptors draft just about anybody in 2017. But, instead, due to injury concerns, former lottery prospect Anunoby fell to them at 23. O.G. has become such a good player for the Raptors that some fans occasionally confuse him for being better than Siakam. This last season he made 2nd Team All Defense, only the second Raptor ever to do that (because they always trade away all the best defensive players). And then, of course, there was this:

2. Leonard and Green for DeRozan and Pöltl – Average = 2.5

Raptors get:

  • Kawhi Leonard, SF:
    • 9.5 Win Shares
    • 4.7 VORP
    • 4.9 playoff Win Shares
    • 2.9 playoff VORP
    • Championship value: 1st in Win Shares (by over double 2nd), 1st in BPM and 1st in VORP (by nearly triple 2nd)
  • Danny Green, SG/SF:
    • 5.9 Win Shares
    • 2.2 VORP
    • 0.8 playoff Win Shares
    • 0.2 playoff VORP
    • Championship value: t-7th in Win Shares, 10th in BPM and t-6th in VORP

Spurs get:

  • DeMar DeRozan, SG/SF:
    • 20.9 Win Shares
    • 7.1 VORP
    • 0.8 playoff Win Shares
    • 0.4 playoff VORP
  • Jakob Pöltl, C:
    • 24.6 Win Shares
    • 6.5 VORP
    • 0.7 playoff Win Shares
    • 0.1 playoff VORP

On July 18, 2018 the Raptors traded their franchise player DeMar DeRozan, plus recent top 10 pick Jakob Pöltl for disgruntled and off-injured Spurs star Kawhi Leonard and playoff hero Danny Green. We all know what happened next.

Personally, this is #1 on my list, but the metrics say it’s 2nd because the Raptors lose the trade on regular season numbers. But the reason to have an NBA team is that one day it will win a championship. And, prior to July 18, 2018, I just didn’t believe it was ever going to happen for the Raptors. This is the trade, and the only trade, that made the 2019 championship possible.

Pöltl of course we have already discussed twice above, both the trade that gained his pick, and the trade that brought him back are wins (so far, in the latter case). He began as the backup centre for the Spurs but soon became the starter. Though he is not a modern centre in any sense, he is succeeding in the NBA despite his shooting limitations. He remains one of the better players in his draft class.

DeRozan was drafted 9th overall in 2009, DeRozan became the default Raptors franchise player after the Chris Bosh sign-and-trade. I for one think DeRozan basically became the best version of himself. When he was drafted, I remember thinking if he becomes a 20 PPG scorer in the NBA, we did well. And he did that. As of right now, he’s the 3rd best player in his draft by Win Shares, tied for 8th in BPM, and 5th in VORP. He is one of the great Raptors draft success stories.

For the Spurs, he came in to help transition from the Duncan-Parker-Ginobili era to whatever the future was. He was supposed to be the second star to LaMarcus Aldridge but he supplanted him as the star almost immediately. During his tenure with the Spurs, they made the playoffs once.

Though Green had one of the worst 3-point shootings stretches of his career during the Raptors’ championship run he still proved a valuable part of the team, especially during the regular season. Given his age, and the inability to retain Leonard, it made sense that he left in free agency. He was last seen play in a few games for Cleveland.

There isn’t much to say about Leonard. It doesn’t matter that he didn’t re-sign. (Though if he did, count me among those who think the Raptors beat the Celtics, beat the Heat and possibly even beat the Lakers in 2020.) He is more responsible for the championship than anyone else and it’s not even close. In the 2019 playoffs, on the Raptors, Leonard is

  • 1st in Minutes (by 38)
  • 1st in Points (by 277)
  • 1st in Rebounds (by 47)
  • 2nd in Assists
  • 1st in Steals (by 9)
  • t-3rd in Blocks
  • 1st in PER (among players who played more than 2 games – by more than 10)
  • 1st in Win Shares (by over double)
  • 1st in WS/48
  • 1st in BPM (by 3.1)
  • 1st in VORP (by nearly triple)

Without this trade, the Raptors are still a franchise without a championship.

1. Lowry for Forbes and a Pick – Average = 1

Raptors get: Kyle Lowry, PG:

  • 74.5 Win Shares
  • 31.8 VORP
  • 7.6 playoff Win Shares
  • 3.6 playoff VORP
  • Championship value: 2nd in Win Shares, 5th in BPM and t-2nd in VORP

Rockets get:

  • Gary Forbes, SG/SF – 0 GP for the Rockets
  • 2013 1st Rounder (Steven Adams) – 0 GP for the Rockets

On July 11, 2012, the Raptors traded their 2013 1st round pick and backup shooting guard Gary Forbes to the Rockets for the Raptors starting point guard.

It should come as no surprise that, if regular season Win Shares and VORP are taken into account, the best trade in the history of the franchise is for the player who many view as the Greatest Raptor of All Time. Whether or not we adjust for the championship, Win Shares and VORP say this is the trade that the Raptors have gained from in their existence. Now, that doesn’t take into the opportunity cost of, say, not having the 12th overall pick in the 2013 draft (and therefore not drafting Giannis, like 14 other NBA teams) but, given the actual play of the players in these deals, this is the best trade.

Forbes played 713 minutes for the Raptors after playing 791 minutes for the Nuggets the year before. He never played another NBA game after this trade. He has played all over the world since. But it’s safe to say that the Rockets wanted the pick, not the player.

But they traded that pick. Now, they traded that pick in the Harden deal, so it worked out for them but, as far as this specific trade is concerned, they got nothing out of it from the players involved.

Whereas it worked out pretty well for the Raptors. Beginning as just another in the long line of attempts to replace Calderon as the Raptors lead guard, Lowry eventually became the face of the franchise. He is

  • 2nd in Games
  • 2nd in Minutes
  • 2nd in Points
  • 6th in PPG
  • 1st in Assists (by over 1000)
  • 4th in APG
  • 1st in Steals
  • 4th in SPG
  • 4th in Rebounds
  • 7th in PER
  • 1st in Win Shares (by nearly 13)
  • 5th in WS/48
  • 2nd in BPM
  • 1st in VORP (by over 5)

You can understand why many people view him as the Greatest Raptor of All Time. And so that makes this the Greatest Raptors Trade of All Time, at least in a sense.

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