🦖🍁 TORONTO RAPTORS ~~ #WeTheNorth 🍁🦖

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.