A Quick History on the Raptors Star Players & The Trades They’ve Been A Part of

So with as much chatter as there’s been with Pascal Siakam, I thought it might be a good idea to take a look at prior trades involving the Raptors most notable franchise players. For the purposes of this sort of retrospective piece, we’re only going to be focusing on the Raptors side of things, though fans of the other teams involved, feel free to chime in on your side of the trade if you’d like.

**Damon Stoudamire**

**The Trade: Damon Stoudamire to the Blazers, Kenny Anderson, Gary Trent Sr., Alvin Williams, 2 first-round picks to the Raptors**

Yeah, we’ll get to Vince in a moment…

Damon Stoudamire often gets overlooked when talking about the early days of the Raptors expansionist woes but the franchise’s first face was anything but un-noteworthy. A sub-6′ shoot-first PG, Damon “Mighty Mouse” Stoudamire went from being booed on draft night by fans to winning hearts of fans and the Rookie of the Year, always threatening to drop a 20 point-double double during his brief tenure as Toronto’s point guard of the future. Stoudamire was so good, he led the Raptors to one of the 10 losses the MJ-led Bulls suffered in 1996, scoring 30 points and showing what a bright future the team might have with Damon at the helm…even if the 96 Raptors went 21-61 that season but I digress.

Damon is also worth not forgetting about because his breakup with the franchise would become something of a pattern for future stars, and it could be argued that Damon’s exit set the stage for more well-known exits like Tracy McGrady leaving in free agency and a certain #15-wearing superstar we’ll touch on momentarily. For now, it needs to be said that Damon’s leaving highlighted how ineffectual the Raptors management looked and only further added to how undesirable Toronto was as a mediocre expansion team, a reputation that would take well over 2 decades for the team to truly shed.

So…Glen Grunwald. Far from the best GM we’ve had, he tried to trade Damon Stoudamire to the Rockets in a deal that eventually never happened, one that Damon found out about and was so angered by that he flatout said he wouldn’t re-sign with the Raptors and berated Glen, saying that “he has no idea what he’s doing”. Damon also said “either trade me or don’t, don’t play mind games” and he eventually got his wish, getting moved to Portland in February 13th, 1998.

Given that context, it’s sort of surprising how much the Raptors were able to get back for a disgruntled star, and bear in mind that this was before rookie contracts would lead to restricted free agency; back in the day, once a player’s rookie deal was up, they were an unrestricted free agent so there was significantly less team control so to get two picks and a handful of decent players was something of a solid deal. What the Raptors ended up doing with those picks…the less said about it, the better.

That said, the Raptors did make one solid move with the players and picks they got back; Anderson was moved with two other players in a subsequent deal that ended up netting them Chauncey Billups, a future All-Star and a late bloomer at that…just not for the Raptors as he got moved to the Nuggets in a series of transaction that would eventually lead to Antonio Davis playing for Toronto. A step down from Marcus Camby (who the Raptors had traded to acquire Charles Oakley) but not the worst center in the world and he stuck around for quite some time as a swingman. Still, considering the Carter era’s struggles at point and Chauncey’s career in comparison, one would have preferred to keep the future All-Star PG if only to pair him up with Vince.

Of the players in this deal, Alvin Williams was the longest-tenured and easily the most notable, sticking around for over 400 regular season games, over a dozen playoff games and would eventually become a commentator for the Raptors in 2021.

Not the best deal in the world but it’s certainly not the worst.

We’re about to get into that one.

**Vince Carter**

**The Trade: Vince Carter to the Nets, Eric Williams, Aaron Williams, 2 first-round picks to the Raptors**

You might have noticed I didn’t include Alonzo Mourning in the trade. We’ll get to that later.

Similar to Damon’s status as the Raptors first star and how good he was before injuries sapped him of his capabilities, I feel like time divorcing people from Vinsanity, coupled with Vince settling in to a lengthy tenure as a veteran on a number of teams – he holds the record for number of most seasons played by an NBA player at 22 – has gotten a lot of people to forget just how good Vince Carter was, to say nothing of his popularity.

A near 40% shooter from 3 between his rookie season and his grumpy exit from Toronto, the Raptors first bonafide superstar was sight to behold. Athletic beyond words, the greatest dunker of all time, 7th in 3-point shooting overall, Vince Carter was an incredible player in his prime as long as you weren’t expecting him to play defense. While the Raptors post-Stoudamire struggles were greatly exaggerated, there is no denying that the Raptors’ 2nd Rookie of the Year improved the team’s popularity and Toronto’s place in the standings. In that time, Vince averaged 24/5/4 on 44/39/79 splits and he showed up in the playoffs for the Raptors deepest run until the DeMar/Lowry era, culminating in an incredibly memorable, if inconsistent, duel with the then-MVP Allen Iverson for a 7-game epic, with said series concluding with Vince’s last-second buzzer beating attempt.

But Vince wasn’t just a great player, he was also incredibly popular. To put Vince’s popularity into perspective: The man was a perennial All-Star, voted in to start for the East for years. He was so popular, he was voted in to start for the All-Star lineup over Wizards Legend™ Michael Jordan in what the GOAT announced would be his final season (Vince would eventually step down and let Jordan take his starting spot), and this was with Vince having missed significant time due to injury.

On a personal note, Vince Carter was my first “star” and the guy who got me into the Raptors. I remember my dad taking me to see him play in both the regular season as well as the Knicks revenge series in 2001 and it was incredible to witness him dunking and jumping as though gravity was more of a suggestion than a matter of physics.

As a kid, I was upset at the Nets trade because my favorite player at the time was gone. As an adult and with all the growth and maturity that has come with adulthood, this trade upsets me even more because of how bad it is.

Say what you will about the Bradley Beal trade, at least Jordan Poole could be something. For the Raptors, the Williams weren’t exactly great supporting pieces to place beside the promising young Bosh and Alonzo Mourning, the one player who might he made meaningful contributions either on the court or in the locker room, flatout refused to show up for Toronto, eventually leading the team to waiving him. The draft picks the team got were used in a salary dump of Jalen Rose and the other was blown on Joey Graham, a player most notable for being picked one spot ahead of All-Star Danny Granger.

Did I mention this deal was bad? If I did, that would be an understatement, it’s hands-down the worst trade the Raptors have ever made and it set the team back for years. It was awful at the time and it only looks worse in hindsight. There are deals you could argue are worse like the infamous deal that led to the Lakers drafting Magic Johnson or any number of underwhelming sign and trades like what the Lakers got back for Shaq but it’s hard to find a regular trade where you look at it and immediately go “Seriously? That’s it?” given the player involved and them being under contract for as long as Vince was; at the time, he was on a fresh 6-year max contract.

Now, there are a few factors that did contribute to an underwhelming return. I briefly touched on it but Vince had developed a bit of a reputation as being injury-prone so that lengthy contract may have been seen as more of a risk than a benefit, and he further sunk his stock by refusing to play up to his previous level; the before/after Nets numbers for the season only highlight how Vince quit on his team.

Vince Carter’s exit from Toronto is equal parts wild and wrath-inducing because of how petty and immature both management and Vince came across, and it could frankly be the subject of a Last Dance-like documentary with all the twists and turns it takes; I didn’t even get into the alleged fight that Vince got into with his coach or the rumor that Vince tipped off the opposing team to a play in a close game that we don’t have time to get into.

Needless to say, Glen looks incredibly foolish to not have traded for Dirk and Nash when such a trade was on the table. No, really. [That was an option in the early 2000s](https://bleacherreport.com/articles/1099048-report-raptors-denied-vince-carter-for-nowitzki-nash-trade-in-early-2000s)!

That said if the Raptors did accept that trade, they probably would never have drafted the next player in this pseudo retrospective…

**Chris Bosh**

**The Trade: Chris Bosh to the Heat, 2 firsts (TOR, MIA in 2011) to the Raptors, TPE**

Bosh’s tenure with the Raptors is perhaps the most frustrating era in the franchise’s history. In his prime, Chris was one of the best power forwards in the league, a two-way player who could give you 25+ a night while playing amazing defense. He was the kind of stud you could easily have build a title contender around or at the very least a constant threat in the playoffs.

The problem was that Bosh was all the Raptors had at the time aside from the ever underrated undrafted stud José Calderon.

They botched their draft picks (Bargnani before Aldridge, Araújo before Iguodala), the one notable free agent they landed, Hedo Türkoğlu, was a colossal disappointment and most of their other moves around the margins failed to make the team around Bosh better, and did I mention they failed to make use of what they got back from the Vince Carter trade? The closest the team ever got to a co-star was one season of Mike James where he put up over 20 points and shot over 44% from 3 on almost 5(!) a game which considering this was 2005/06, was doubly impressive for the time.

After James left, Bosh never had anywhere close to that level of help on offense and yet…CB4 was somehow able to bring some of the sorriest Raptors squads you’ve ever seen into the playoffs. Granted, both berths ended in a first-round exit, and only 3 wins between the two series, but still, Bosh proved he was more than a “good stats, bad team” player after departing to the Miami Heat where he honed down on his defensive prowess and became the archetype for the modern PF, the “stretch 4”.

As for the return received from South Beach, it was…underwhelming to say the least. No players or prospects, just a massive trade exception that ended up going to waste, the Raptors getting their own 2011 pick back – they traded it to the Heat for one of those aforementioned moves that never worked out i.e. acquiring Shawn Marion for a single season (they sign and traded him in the offseason he became a free agent and Marion would go on to be a key contributor to the 2011 Mavericks title) which itself was an effort to fix the Jermaine O’Neal experiment – and a lottery-protected first from the Heat.

One thing that does need to be understood is that this was a sign and trade so the return was never going to be all that great. That said, this actually became one of the more consequential trades in hindsight.

The Heat’s pick ended up being traded in a deal for James Johnson which, unless the Raptors planned on taking **Jimmy Butler** who, you guessed it, was chosen a few spots after the player who the pick was eventually used on (Norris Cole), ultimately ended up just being a bad deal. The more interesting part is the Raptors pick.

In case you’re wondering, the Raptors pick was lottery-protected and it had those protections from 2010 until 2015. While that does sound like this deal wouldn’t have mattered given where the Raptors were for some time i.e. they would still end up drafting Jonas Valančiūnas and Terence Ross in 2012, consider this:

* In the 2012/13 season, the Toronto Raptors traded their 2013 pick as part of a deal to acquire **Kyle Lowry**. Lowry would go on to become the franchise’s GOAT and was a key piece to the 2019 championship but the overall season he was acquired ended up being disappointing and there was a lot of speculation as to whether Lowry would stay with the Raptors in the long-term for a variety of reasons. We’ll get on to the impact of that in a moment but without the Bosh sign and trade, either Lowry never becomes a Raptor or a different, future first gets traded instead; due to the Stepien Rule, it would have to be between 2017-2019. That becomes important when you consider…
* The Raptors 2013 pick ended up being 12th overall in the lottery and found its way over to the Thunder. In case you’re wondering, yes this is the draft where [Masai Ujiri desperately tried to get back into the lottery](https://www.youtube.com/watch?v=Ficds0wx8bY&pp=ygUNbWFzYWkgZ2lhbm5pcw%3D%3D) to draft **Giannis Antetokounmpo**, a future Hall of Famer, All-NBA caliber player and 1x NBA Champion/Finals MVP.

If the Raptors still owe a future pick to the Heat, it’s very likely that they would end up drafting Giannis though whether or not he’d develop into the same player he is today, whether a Giannis/DeMar duo would have made waves and whether or not they’d still acquire Kyle Lowry/who would end up not being drafted by the Raptors in the future either due to team record or pick availability (including players that the Raptors traded for using their own pick i.e. trading T-Ross and a pick for Serge Ibaka) is a massive “what if” that we don’t have time to speculate on. And again, we’re not even considering they could have drafted Mr. Buckets himself or whether drafting Giannis means the Raptors don’t go after Bruno “two years away from being two years away” Caboclo. There’s so many different ways this franchise could have gone as a result of their pick’s availability in the 2010s.

And all of this because they agreed to a sign and trade for Chris Bosh. Life is funny sometimes.

**DeMar DeRozan**

**The Trade: DeMar DeRozan, Jakob Poeltl, 1st round pick (Top 10 protected ) to the Spurs, Kawhi Leonard & Danny Green to the Raptors**

You know this trade.

I know this trade.

I’m not going to waste your time talking about how good of a trade this was since it led to a championship and how little was given up, even if Kawhi did leave for nothing after the Raptors got their first ring and the only one to date.

All I can really add to the conversation is that…I really miss DeMar and I really wish he got an opportunity to get a ring given some of the misfortune he faced in San Antonio and the Bulls, namely with Chicago losing Lonzo due to injury when they were 1st in the East with a dominant 27-13 record in 2021/22.

It really does suck to see the former face of the franchise and his legacy reduced to “the guy the Raptors traded for Kawhi”. Yes, DeMar had his playoff struggles and yes we all know what LeBron did to the Raptors in consecutive postseasons but DeMar was a major reason why the Raptors reputation as a franchise turned around and made them into a major player in the East, constantly boating 50+ wins every season; the 2017/18 season’s 59 wins remains the franchises highest of their regular season record, the CO-VID-shortened season where they were on pace to win 60 games (53-19) notwithstanding given how much turmoil the Raptors were dealing with after the season’s break, namely with Pascal Siakam’s postseason struggles.

Let it not be forgotten how the duo of DeRozan and Lowry led the Raptors to their first ever conference finals, nor that DeMar held his own in that 6-game series against LeBron. DeMar still holds the franchise record for points – and it’s not even close between him and 2nd place being separated by over 3,000 – and field goals, among many other categories and regardless of whether he returns to retire a Raptor or not, let it never be said he was anything less than a legend for the franchise.

**Kyle Lowry**

**The Trade: Kyle Lowry to the Heat via sign and trade, Goran Dragic & Precious Achiuwa to the Raptors**

After the DeMar trade, there was no way the Raptors could simply “conduct business” and just trade away the most important player in franchise history. There’s nothing stopping them, technically, but while Toronto isn’t exactly a haven for free agents, they’d be even less desirable a place after what they did to DeMar and if they .

Even if one thinks a combination of…

* KCP, Dennis Schroder and draft capital from the Lakers (THT was never included and was seen as the dealbreaker)
* Matisse Thybulle and/or Tyrese Maxey from the 76ers (The sourcing on this one is really hard to find the exact package)
* A combination of Goran Dragic, Kelly Olynyk, Duncan Robinson or Kendrick Nunn from the Heat
* Whatever package I may have missed

…were truly on the table at the 2020/21 deadline, Lowry wanted to stay during the Tampa Tank, he wanted to go to Miami in the offseason and thus, here we are with the package of Precious Achiuwa and the infamous Goran Dragic received via a sign and trade.

Precious is a player who i’d argue embodies the Raptors most recent seasons: There are moments of true brilliance from Precious, where his raw athleticism comes together and you can see the two-way star he could yet be. His combination of size, speed and versatility is truly special…

…and then there are the plays where one wonders how Achiuwa is getting minutes whatsoever with some truly baffling possessions of defensive decision-making. There’s [this one play](https://www.youtube.com/watch?v=MO9FCUGtO9w) with fellow Raptor Chris Boucher that I feel summarizes Precious. Boucher passes the ball to Precious, Achiuwa almost loses the ball then somehow turns it into a super satisfying dunk with a single leap to the basket. It is, in a word, art.

His shooting had one particularly hot period post-2022 All-Star Weekend but whether or not that was a fluke given how cold he was from beyond the arc in 2022/23 remains to be seen; Precious isn’t exactly a volume 3-point scorer so we’re still operating with a relatively small sample size.

Being charitable, his inconsistencies could be the result of lacking a defined role but if nothing else can be said about him, Precious’ bizarro brand of basketball was one of the few highlights of the most recent season despite missing significant time due to injury and struggling throughout.

So one half of this trade is a mixed bag but trending towards the positive. However there’s the other half of the trade, one which ended up being highly consequential in the long-run.

Goran Dragic is only less contemptable than Alonzo Mourning because Mr. “Higher Ambitions” actually did suit up for the Raptors, albeit briefly and his aforementioned – and [mistranslated/misconstrued](https://www.cbc.ca/sports/basketball/nba/goran-dragic-comments-raptors-trade-heat-1.6136129) \- comments loomed over his brief time with the team. Although an ill fit for the team’s playstyle, there was at least some optimism he could have filled the role of a veteran for Scottie Barnes and serve as the team’s backup point guard, a role which had been more or less left absent in the Tampa season as Fred VanVleet was promoted to the starting lineup in 2019/20.

He ended up spending more time in Miami than he did in Toronto. In fairness to Dragic, there were allegations that he was going through some personal issues that rightfully should have taken priority but we’ll never know if there was any validity to them or whether Dragic simply did not want to play so far away from Miami; he was even [spotted watching a couple of games for the Heat](https://twitter.com/TheNBACentral/status/1487251136931319809) when the Raptors were going through something of a rough patch.

So a veteran didn’t want to play for a team full of mostly younger players at the time like Justin Champagnie and Dalano Banton. It’s not the end of the world even if said veteran didn’t come out of it looking particularly great and it led to Toronto fans showering him with boos. The animosity between he Raptors and Dragic sparked something of a prolonged disdain for the old dragon after he [tweeted out a series a laughing emojis](https://twitter.com/TheNBACentral/status/1519856610939703296) after the Raptors lost to the 76ers in 6 games despite him getting swept by the Celtics, as Goran would continue to be [showered in thunderous boos](https://www.youtube.com/watch?v=OykEQ0BaLN0) in subsequent appearances when playing against Toronto at home. With Vince having been retired for years, it’s about the closest thing you’ll get to seeing that good ol’ vindictiveness Carter would enjoy from the Raptors most vocal fans.

The big problem was Dragic’s salary and finding a team willing to give up anything for him straight up. Due to the lack of play, his age and the size of the contract, it was a difficult affair to find a partner; the most commonly linked partner was the Mavericks who at one point were considering trading Kristaps “[Alleged to have raped a woman in 2018](https://www.espn.com/nba/story/_/id/26401287/report-porzingis-accused-rape-new-york)” Porziņģis for Dragic and a first-round pick but the Raptors weren’t willing to include Gary Trent Jr.

In the end, the Raptors gave up their 2022 first round pick and Dragic in order to acquire Thad Young, a player the Spurs were planning to waive, Drew Eurbanks – a player the Raptors ended up waiving – and a second round pick via the Pistons that ended up being Christian Koloko.

Koloko is a decent bench center but the Thad Young trade…was bad. Functionally a salary dump, the deal had three main consequences.

First, the Raptors missed out on two players late in the 2022 draft in Walker Kessler and Andrew Nembhard, both of whom would have filled major holes in the roster and one of whom the Raptors were alleged to have been targeting at the time with the 33rd pick in Andrew (he was picked 31st). Skipping out on Walker Kessler in particular is a move that came to haunt the Raptors in the 2022/23 season as Kessler played a key part in two of the most infuriating losses Toronto would incur that season, one of which happened right after the trade deadline.

Secondly, that trade at the deadline ended up being for Jakob Poeltl, a player that added yet another UFA for the Raptors to sign, and a late addition to a team several games under 0.500 with only 26 to go. If the Raptors had drafted Kessler at 20 or wherever the Raptors ended up without Thad Young, it’s unlikely they would have made such a highly consequential deal to fill their gaping hole at the center position (that they left open for 3 seasons) where they gave up a first-round pick to the Spurs for a pick with worse protections than the one given up for Kawhi Leonard, and bear in mind that the Raptors were 10th in the standings at the time with the 7th-best odds in the 2023 lottery. That light of a protection with that record when you could very well lose your main guards in Gary Trent Jr. (he opted in) and Fred VanVleet (he’s gone), to say nothing of the financial wizardry to avoid going into the tax in the next few years with yet another UFA to sign vs. having a productive rookie in Walker Kessler on a team-friendly deal for 4 more years is monumentally baffling.

Third, even if one operates under the assumption that Koloko would have been the guy at 20, an unlikely assumption given Koloko was projected to be a second-round pick, said pick would top out at 3 years as opposed to the 4 that a first-round pick entails, so while they may have saved some money in the short term between Dragic and Koloko’s salary being lower than paying the rest of Goran’s salary/buying him out and signing whomever at the rookie salary the 20th pick or so would have gotten, in the long run they’re going to have to make a decision to either keep or trade Koloko much sooner than expected.

Irrespective of who they would have picked if they kept their 1st rounder/if they would have made a draft day trade, irrespective of whether Christian Koloko, Walker Kessler or Andrew Nembhard end up being the better player amongst the three, this was a bad move and sours an otherwise okay deal.

Considering it was a sign and trade, getting back Precious Achiuwa for an aging Lowry? Not that bad even if one imagines they would have preferred Duncan Robinson’s not great contract to dumping Dragic. It’s going to be interesting to see this one age given how recent this one was and how likely it is Koloko and Achiuwa will be key players in the Raptors rotation next season.

by CazOnReddit