Four trades from Toronto Raptors history when they went all-in for a star

1999: Antonio Davis for a high-school phenom

It worked once so why not try it again? After acquiring Oakley from the Knicks, Grunwald went after another veteran center, this time acquiring 31-year-old Antonio Davis from the Indiana Pacers. Davis was a late-bloomer, making his NBA debut at the age of 25 while starting his pro career overseas. After six seasons in Indiana with 67 playoff appearances, Davis was acquired by the Raptors in exchange for the fifth overall pick in the 1999 NBA Draft, Jonathan Bender. 

Now this really wouldn’t happen in today’s NBA.

Bender was a McDonald’s All-American and was highly touted to become one of the best pure scorers in the NBA. Unfortunately, injuries played a huge part in his NBA story. In his seven seasons with the Pacers, Bender played only 237 games and was out for three straight seasons before a short stint with the Knicks in 2010.

For the Raptors, Davis blossomed alongside Carter and earned himself an All-Star nod in 2001 while averaging 12.9 points per game across parts of five seasons – it’s safe to say the Raptors were on the right side of the history books on this one.

2008: The duo that never was – Jermaine O’Neal

Unfortunately for Raptors fans, the Indiana Pacers got their revenge from the Bender trade after making a deal that sent Jermaine O'Neal to Toronto in 2008. O’Neal played a vital role in Indiana’s success across the 2000s, making six All-Star appearances and three All-NBA teams, although he struggled with injuries in his later years with the team.

The Raptors were coming off back-to-back first-round exits and GM Bryan Colangelo needed to change something if there was any hope of resigning Chris Bosh who was up for free agency in two years. The Raptors decided to make the deal on draft night, acquiring O’Neal in exchange for T.J. Ford, Rasho Nesterović, and the 17th overall pick.

Who did the 17th overall pick turn into? Two-time All-Star Roy Hibbert.

Hibbert practically turned into the player that the Raptors were looking for, playing as a defensive force for the Pacers in the playoffs during the Paul George era. O’Neal and Bosh struggled to co-exist on the court, the Raptors struggled to win games, and before you knew it O’Neal was traded out of Toronto two just months later near the deadline to the Miami Heat in 2009.

One of Bryan Colangelo’s many mistakes as GM for the Raptors.