NBA Draft: The best picks in Toronto Raptors history

The 2020 NBA Draft will finally get underway on Nov. 18 after the COVID-19 pandemic altered the league calendar as we know it. This year, the Toronto Raptors hold the 29th and 59th selections among what’s unfortunately considered to be the least promising class since 2013.

Draft night has often been fraught with anxiety for Raptors fans, although under Bobby Webster and Masai Ujiri’s watch, the club has developed a strong reputation for being able to come away with steals, with the organization’s prospect development system second to none.

Ahead of draft night, here are the five best draft picks in Raptors history. For the purpose of this exercise, undrafted players aren’t considered, therefore, Fred VanVleet was eliminated from this list.

Chris Bosh

Bosh’s decision to join the widely-loathed Miami Heat in 2010 may have caused some to overlook his impact while with the Raptors. Selected fourth overall in the vaunted 2003 NBA Draft, Bosh exceeded expectations coming out of Georgia Tech as the No. 4 pick and built the foundation for his Hall of Fame resume while with the Raptors.

In his final season with the Raptors, Bosh averaged a career-best 24 points and 10.8 rebounds, while shooting 51.4 percent from the field and 36.7 percent from 3-point range. It was a crushing blow when he left to play alongside LeBron James and Dwyane Wade. History may remember Bosh more for his contributions with the Heat as a third option and lethal pick-and-pop player in the mid-range, but he was no slouch in Toronto, earning five consecutive All-Star selections and his lone All-NBA Second Team nod in 2007.

Bosh still holds several franchise records and though his tenure may have ended acrimoniously, he could be the first player to enter the Hall as a Raptor.

DeMar DeRozan

DeRozan has now been supplanted by his best friend, Kyle Lowry, as the greatest player in franchise history. It’s a bittersweet accolade for DeRozan, who wanted to spend his entire career with the Raptors. It was a tough decision for all parties involved, but when Kawhi Leonard (and Danny Green, and $5 million in cash) are available, you have to sometimes make gut-wrenching decisions.

Selected with the No. 9 pick in the 2009 draft, DeRozan provided excellent return on value and while his classmates James Harden (No. 3 overall) and Steph Curry (No. 7) redefined basketball as we know it, DeRozan made an immediate impact on the Raptors by his second season. During his nine seasons, DeRozan became the face of the franchise, a beloved member of the community and earned four All-Star game selections, along with two All-NBA picks.

DeRozan still stands as the Raptors’ all-time leading scorer and is perhaps the avatar of the organization’s commitment to becoming a perennial playoff contender. Although no one will mistake him for Harden or Curry, DeRozan is the third-best guard from a historic class, and while history may remember him as the key piece in the Leonard deal, he will always have an indelible mark on the Raptors.

Pascal Siakam

Siakam very well could end up atop this list when his career ends. For now, all Siakam has done is emerge as a significant part of the Raptors’ first championship run, won NBA Most Improved Player for 2018-19, then earned his first All-Star selection, to go along with All-NBA Second Team honours in 2019-20.

The members of the 2016 class are still reaching their peak, but Siakam and Philadelphia 76ers star Ben Simmons are the only players to have been named to an All-Star game and an All-NBA team in their careers thus far. At the time of the draft, the vast majority of fans and analysts wanted the Raptors to select Skal Labissière or Deyonta Davis with the No. 27 pick. When Siakam, a largely unknown quantity, was taken by the Raptors, it was preemptively dismissed as a bad pick, a reach, and many wanted to know why the Raptors took a senior who needed time to develop.

The fear of the unknown can be a real curse to some. Siakam easily dismissed any concerns about whether the Raptors made the correct choice. Now he’s a foundational piece of the most successful era in franchise history. He isn’t going anywhere soon, after signing a four-year, $130 million max extension prior to the 2019-20 campaign. If Siakam can elevate his game to another level as the No. 1 option and continues on the sky-high trajectory he’s shown to date, he has the potential to become the singular all-time best pick in franchise history.

Vince Carter

There isn’t anything particularly novel about the man known as “Half Man, Half-Amazing” but since we’re here, Vince Carter was the first person to put his definitive stamp on basketball in Canada. Carter became the best in-game dunker in NBA history (if you want to stan Michael Jordan instead, have at it), putting the organization on the map with his iconic performance in the 2000 Slam Dunk Contest. His prolific dunks alone would warrant a place on this list, but Carter was one hell of a ball player and if you excuse Damon Stoudemire’s rookie season, became the Raptors’ first genuine star.

Carter was named an All-Star five times while with the Raptors. At the peak of his career, Carter left the Raptors under acrimonious circumstances by demanding a trade, which came to fruition when he was sent to the then-New Jersey Nets. As a result, Carter was loathed in Toronto, routinely booed and was considered persona non grata for several years.

Time heals all wounds, however, and Carter was visibly touched when the Raptors honoured him during a video montage as part of the team’s 20th anniversary celebrations in November 2014. Carter truly has come full circle in Toronto, becoming the team’s first superstar, its first villain, and now holding a place as a beloved alumnus, waiting for his jersey to be hung in the rafters.

After Dirk Nowitzki and Paul Pierce, Carter, who was taken fifth overall in 1998, will likely be considered the third-best player from his class, but his dunks and his time with the Raptors will live forever.

Tracy McGrady

Tim Duncan went first overall as expected to the San Antonio Spurs, while some may have forgotten that Chauncey Billups started his career with the Boston Celtics after being taken with the third pick. With due apologies in order, Duncan emerged as the only player from the 1997 class definitively better than Tracy McGrady, a rangy, lanky high school swingman out of the Mount Zion Christian Academy who fell to the Raptors at No. 9 overall.

McGrady joined Duncan as the only Hall of Famers from that class, but it would be revisionist to say that the Raptors, or any other team for that matter, could’ve envisioned his career arc playing out as it did. Although Kevin Garnett (1995) and Kobe Bryant (1996) preceded him, it still wasn’t fashionable to take high school players, especially in the lottery. McGrady began to break out during this third year, averaging 15.4 points and 6.3 rebounds per game during the 1999-2000 season.

However, McGrady’s third season with the Raptors would be his last, and his career began to propel to new heights. McGrady was named the NBA’s Most Improved Player after signing with the Orlando Magic ahead of the 2000-2001 season, earning the first of seven consecutive All-Star selections. Objectively, the Raptors received a decent return on value, but McGrady is often seen as The One Who Got Away. It is still a stellar pick for the Raptors, but considering that he only began to show signs of a Hall of Fame career after leaving Toronto, McGrady is docked points here.

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