Toronto Raptors: Best trade in team history with Boston Celtics

The Toronto Raptors might play in the same division as the Boston Celtics, but some parts of that fanbase haven’t viewed the Raptors as one of their main rivals, likely because this franchise was overflowing with championships before the Raptors even came into existence in the 90s.

Still, these two teams have had some really intriguing battles over the years. Be it Vince Carter and Paul Pierce going shot for shot, Chris Bosh and Kevin Garnett facing each other or the wars that took place as recently as 2020 in the bubble, Boston and Toronto have made for good enemies every now and again.

Toronto and Boston, likewise, very rarely trade with each other, as they have made just two such transactions between them. One of them, however, was clearly won by the Raptors.

The Raptors acquired Chauncey Billups, the No. 3 pick in the 1997 NBA Draft, along with Dee Brown, Roy Rogers, and John Thomas from the Celtics. Toronto gave up Kenny Anderson, Popeye Jones, and Zan Tabak.

The Toronto Raptors made out alright in this trade with the Celtics.

Before Billups embarked on a long NBA career with the Pistons and Nuggets, he was a rookie point guard for Rick Pitino’s Celtics.

After Pitino said that he “wasn’t my kind of point guard” following weeks of berating him from the sidelines, he shipped Billups to Toronto for Kenny Anderson, who never played a game for the Raptors after being included in the Damon Stoudamire trade.

While Anderson played five years in Boston, he averaged just 11.3 points per game, well below his average with the Nets, and rarely even made the postseason. Jones and Tabak struggled to get minutes. Billups and Brown had some moments with Toronto, but it was how the Raptors ditched Billups that made them the winners of this trade.

Needing a center, Billups was dealt to the Nuggets for the No. 5 pick in the 1999 NBA Draft. The three-way deal between Toronto, Denver, and Minnesota also helped the Raptors get a first-round pick in 2000.

While they took Jonathan Bender No. 5 overall, he was flipped to the Pacers for Antonio Davis, who would start 307 games for the Raptors and make an All-Star team while establishing himself as one of the best centers in franchise history.

With the 21st pick in the famously bad 2000 Draft, Toronto came away with Michigan State guard Morris Peterson, who would play seven above-average seasons in Canada. If Toronto had their mind made up about dealing Billups, getting two half-decade starters in exchange by sending essentially a declining Anderson to Boston was a nice bit of maneuvering.

Both teams could look at this trade as a lose-lose situation from a basketball point of view, as Anderson was a bit disappointing in Boston and Toronto ditched Billups right before he found his footing in the NBA.

Still, the Raptors were able to turn the ammo acquired for Billups into two starters for the early parts of the decade. Not a bad way to make lemonade out of lemons.