3 times the Raptors bombed in free agency, and 2 times they reaped the rewards

2005: Jose Calderon (three-year, $7 million)

Now that we got all of that free agency frustration out let’s focus on some of the positives – and yes there actually were some positives for the Raptors in 2005.

Toronto was looking for a point guard they could plug into their rebuild after a yearly carousel of Alvin Williams, Jalen Rose, and Rafer Alston, and decided to sign Jose Calderon – a 24-year-old point guard out of the EuroLeague.

Despite Calderon’s rookie season struggles, the Spaniard turned out to become one of the best pure shooters in Raptors history. Calderon joined the 50-40-90 club in 2008 and set the record for the highest free-throw percentage during the very next season. Calderon was the team’s starting point guard during the Raptors back-to-back postseason appearance from 2006-2008 and played 525 games in Toronto before being traded to the Detroit Pistons in 2013.

The Raptors eye for international talent hasn’t always worked out (especially in the draft), however Calderon’s deal with the Raptors turned out to be one of the best-value deals for the franchise and quite possibly the only positive from the Mike Babcock era. 

1999: Dell Curry (three-year, $6 million)

This is a deal that doesn’t get talked about enough (possibly because it was 25 years ago) but before Steph Curry dominated the NBA, his father Dell was a household name across the league that joined the Raptors in free agency.

Curry was a dominant three-point specialist who is best remembered for his ten seasons with the Charlotte Hornets. After playing the 1998-99 season with the Milwaukee Bucks, Curry had reportedly agreed to return to the Bucks on a two-year extension before Raptors GM Glen Grunwald stepped in with a bigger offer.

The 35-year-old played a vital role as a veteran leader towards the young core of Vince Carter and Tracy McGrady, and served as a valuable shooter off the bench during his time in Toronto which included a trip to the postseason in all three seasons.