Ranking every first-round pick in Toronto Raptors history

In the course of the Toronto Raptors franchise history, there has been a fair share first-round picks walking in the door. How do they rank from worst to first?

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Toronto Raptors - Vince Carter. Mandatory Credit: Ezra O. Shaw /Allsport

24 years of Toronto Raptors basketball has produced some exciting first-round draft picks. Not all have gone so well, as frequent misses in the lottery had seemingly become thematic following the 1998 season. We will take a look at every Toronto Raptors first-round draft pick and rank them from worst to first. That being said, determining how to make a completely subjective list have some objectivity to it was an interesting exercise.

What ‘best’ means needs to be properly defined. Does it mean talent? Does it mean the best career? Does it mean that the pick was considered a steal and/or that the team landed the best player available?

In the end, a combination of the three is the only way to be truly objective. Talent and career trajectory are important, but if the Raptors passed on numerous players of obvious superior talent it will affect their spot in these rankings.

As you will see as you go through these rankings there are superior talents ranked below inferior ones simply because they were not the best player available then, and the optics of the perplexing draft selections have only worsened in hindsight.

To qualify for this list a player had to be a member of the Toronto Raptors at the end of draft night. We will be ignoring that some of these deals could not be consummated until the start of the new league year. This means we will be ranking Vince Carter instead of Antawn Jamison from the 1998 draft class.

It means that Jonathan Bender will not be ranked since he was traded on draft day for Antonio Davis. Kareem Rush will not be ranked as he was traded in a salary-cap related move for the 27th overall pick in Chris Jefferies. Finally, Roy Hibbert will not be ranked as he was also part of a draft-day deal along with T.J. Ford and Rasho Nesterovic for Jermaine O’Neal. Let’s dive in.

Andrea Bargnani - 1st overall (2006)

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Andrea Bargnani - Toronto Raptors. (Photo by Jennifer Pottheiser/NBAE via Getty Images)

2006. The year the NBA barred high school players from entering the NBA Draft. This means no Greg Oden or Kevin Durant in the draft pool. The Toronto Raptors win the draft lottery. Their Italian G.M. in a city with a large Italian population is enamored with an international prospect from his ancestral home of Italy.

There were hopes that Bargnani could overcome his noted lack of rebounding skill and become the type of stretch big that Dirk Nowitzki had become in the NBA. Andrea ‘Il Mago’ Bargnani was a 7-foot big who had a range that extended to the three-point arc. He profiled best as a power forward, but his selection meant either Chris Bos would be forced to play out of position.

Bargnani was a questionable choice at the time, and due to draft capital, will likely go down as the worst first-round pick of all-time by the Toronto Raptors. Other players had less impressive NBA careers, but no other was drafted first overall.

The 2006 draft was still a talented one, even with the high schoolers snatched from the draft pool. LaMarcus Aldridge, Brandon Roy, and Rudy Gay were all in the mix to go first overall to the Toronto Raptors, but Bryan Colangelo was simply too enamored with the Italian big man. Bargnani was such a bust that he soured an entire fan base on European prospects until Jonas Valanciunas came to the Toronto Raptors and changed the fanbases collective minds.

Bargnani averaged 15.2 points and 4.8 points in his seven seasons with the Toronto Raptors. Remember Charlie V averaged 13 and 6.4 as a rookie. Bargnani topped out with 21.4 points, 5.2 rebounds on just under 45-percent shooting in 2010-11. He averaged 17.6 shots per game. ‘Primo Pasta’ as he became known towards the end of his NBA career was a low efficiency big who could hit the three with some regularity but could not defend or rebound.

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Aleksandar Radojevic - 12th overall (1999)

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Toronto Raptors (Photo by Steve Babineau/NBAE via Getty Images)

Arguably the worst first-round pick in Toronto Raptors history, Radojevic played in only 15 NBA games and shot 30-percent from the field. He played only 24 minutes over three games for the Toronto Raptors. He shot 29-percent from the field. I am not 100 percent certain how he got drafted out of Barton County Community College, but here we are 20 years later talking about it.

The 1999 draft was not the strongest. In fact, the most notable name Toronto passed on was drafted 57th overall and was from Argentina. Manu should find himself in the Hall of Fame one day after winning four NBA championships, making two all-star appearances and two All-NBA teams.

Other names the Raptors passed on for Radojevic include the player most think the Raptors should have picked in Corey Maggette at 13, Ron Artest (Metta World Peace) at 16, and Andrei Kirilenko at 24.

This was the Shaquille O’Neal era where every team in the NBA was scrambling for a big man, but adding a player who played at a junior college made little sense then, and makes even less sense now. Perhaps the Toronto Raptors, or more specifically the overmatched Glen Grunwald thought he could swing for a home run in the 7-foot-3 Radojevic since the Raptors had two lottery picks (our fifth overall pick was eventually shipped in a trade for Antonio Davis).

Aleksandar was not even that impressive in college as he averaged only 13 points and 7.6 rebounds in his two years at JUCO. His four blocks per game in his final season looked good, but the level of competition or lack of it has to be factored into any scouting report. The only JUCO players a team should look at are the ones who transferred to a different school prior to the draft or top high school stars who had to go the JUCO route due to grades or other off the court issues.

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Rafael Araujo - 8th overall (2004)

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Toronto Raptors - Rafael Araujo. (Photo by Steve Freeman/NBAE via Getty Images)

Rafael ‘Haffa’ Araujo was one of the biggest wasted picks in Raptors history. Another in a long line of reaches, the selection of Araujo was just as strange as Richard Peddie’s decision to ignore the fact that Vince Carter had got Julius Erving to agree to become the general manager of the Toronto Raptors in favour of hiring the now infamous (and recently deceased) Rob Babcock.

Araujo did have an impressive senior season at BYU but was not the top-rated player available on any other big board. The top player available, and the player that went directly after him at ninth overall was Andre Iguodala. Araujo was not even the top-rated center left on the board as high schooler Al Jefferson somehow slipped to 15th overall.

Araujo would go on to play 111 games for the Toronto Raptors, starting 75 of them. After averaging 18.4 points, 10.1 rebounds at Brigham Young University, he averaged just 2.9 points and 3.0 rebounds in 12 minutes per game as a member of the Toronto Raptors. Bryan Colangelo quickly ended the Araujo ‘era’ as he was mercifully traded in 2006 for a useful rotation player in Kris Humphries.

Araujo was completely overmatched in the NBA and lasted just three seasons. He would go on to spend time in Russia, China, and Brazil. Andre Iguodala is still in the NBA and was named the 2014-15 NBA Finals MVP. Al Jefferson played at a high level for seven of his 14 seasons and made the All-NBA team in 2013-14.

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Michael Bradley - 17th overall (2001

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Toronto Raptors - Michael Bradley. (Photo by Jim Ross/Toronto Star via Getty Images)

Figuring out how to rank the bottom of this list was the most difficult aspect of this process. Michael Bradley was another horrible pick by Glen Grunwald. Suffice it to say that the entire Grunwald era was an unmitigated disaster. Bradley played just five NBA seasons and saw just 15 minutes per game in his three seasons with the Toronto Raptors. His best season came in 2002-2003 when he posted totals of five points and 6.1 rebounds in 19.6 minutes per game.

Bradley would be forced to take his ‘talents’ overseas where he bounced from club to club. He spent time with multiple clubs in Spain. He also saw stints with clubs in Germany and Lithuania.

Another wasted pick in the Shaquille ONeal era, Bradley showed some promise after a transfer to Villanova. He averaged 20.6 points and 9.6 rebounds but was still looked at as a reach at 17th overall. Being unable to carve out a significant role for Kentucky should have been a red flag to the Raptors scouting department.

As with most picks in the Grunwald era, Bradley was a reach. Zach Randolph was still on the board and was quickly snapped up at 19th overall. There were a number of notable players that the Raptors missed on including Tony Parker, Gilbert Arenas, Randolph, Gerald Wallace, Samuel Dalembert, Brendan Haywood, and Jamaal Tinsley.

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Chris Jefferies - 27th overall (2002)

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Toronto Raptors - Chris Jefferies. (Photo by: Fernando Medina/NBAE via Getty Images)

It is hard to fault the Toronto Raptors for whiffing on a pick in the late twenties. The player they ended up trading to the Los Angeles Lakers in Kareem Rush, was an effective role player, but never came close to what most thought his NBA ceiling was. Chris Jefferies, on the other hand, was more of an end of the bench body.

He looked good in college but that was only after he transferred from Arkansas to Fresno State. Jefferies averaged 17.3 points and 6.3 rebounds in his final college season, but he did so on under 42-percent shooting. He played 53 games with the Toronto Raptors, starting 10, and averaged just 3.9 points on 39-percent shooting.

His career highs of 15 points and 5 rebounds goes to show how uninspiring he was in the NBA. He lasted only two seasons in the NBA and played only 19 games in his second NBA season.

The most noteworthy player drafted after Chris Jeffries was Carlos Boozer, a player who while limited, profiled as a superior prospect to Jefferies. Boozer would become a two-time all-star and even made the All-NBA team in 2007-08. Although he was a limited player who had no three-point range and provided little in terms of blocking shots, Boozer was one of the top big men in the league for nine of his 13 NBA seasons.

Other players the Toronto Raptors passed on include Matt Barnes and two players that would end up joining the Toronto Raptors later in their careers in Rasual Butler and Luis Scola. Scola made the all-rookie team despite playing only 24.7 minutes per game. Barnes was a hard-nosed small forward who would have provided a solid stopgap at the small forward position for the Toronto Raptors.

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Bruno Caboclo - 20th overall (2014)

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Toronto Raptors - Bruno Caboclo. (Photo by Vaughn Ridley/Getty Images)

With Gary Harris coming off of the board one pick prior to Bruno Caboclo, Masai Ujiri swung for the fences on a player that was dubbed ‘the Brazilian Kevin Durant’. A raw project player, perhaps Masai was trying to make amends for not being aggressive in his pursuit of Nigerian descendant of Greek passport in Giannis Antetokounmpo in the prior years draft. Masai famously proclaimed that the developmental player was two years away from being two years away.

Caboclo spent the majority of his time as a Toronto Raptors in the NBA G-League. He averaged over 14 points per game with six-plus rebounds in two of his seasons with the Raptors 905. Unfortunately, he was extremely inefficient and still not ready.

Bruno Caboclo played just 25 games with the Toronto Raptors main roster. He averaged 1.1 points in 4.5 minutes per game. Bruno Caboclo was traded for Malachi Richardson during the 2017-18 season.

Perhaps a change of scenery was all he needed because he was able to up his shooting percentage to just under 47-percent from the sub-40-percent level he had shot with the Raptors 905. His play made a marked jump in his fifth season. So perhaps he really was four years away and the Raptors just gave up too soon.

In his fifth season in the G-League, he averaged 16.4 points, 7.2 rebounds, 3.0 blocks, 1.3 steals and 2.4 threes per game. However, it is the percentages that really standout. He was able to spike his field goal percentage to just under 52-percent and his three-point percentage to 43-percent. All numbers worthy of an extended look in the NBA.

Caboclo came to life as a member of the Grizzlies organization. His career highs are enough to make any Raptors fan cringe. He (and remember these are NBA totals) was able to drain four threes and rack up 24 points against the Oklahoma City Thunder on March 25, 2019. He amassed an eye-popping 17 rebounds against the Dallas Mavericks on April 7th, 2019.

Dallas looks like one of his favourite opponents to play against as he handed out six dimes against them on March 2nd, 2019. Also in 2019, he swatted four shots against the Minnesota Timberwolves.

The Grizzlies signed Caboclo to a partially guaranteed two-year deal during the 2018-19 season, and due to keeping him on the roster past the July 10th waiver date, he will make a cool $1.88 million dollars during the 2019-20 season.

Caboclo was a reach when he was drafted, but as alluded to above, his selection was a reaction to the names the Raptors were targeting no longer being on the board. It also very likely had something to do with Masai Ujiri’s regret over not adding Giannis to our roster. The regret has likely become compounded as the Raptors gave up on Caboclo before he started to reach his potential.

The names still on the board could make even the most casual fan shudder. Clint Capela, Bogan Bogdonavic were both around in the twenties. The second round still housed Spencer Dinwiddie and 2018-19 all-star, and one of the top bigs in the league in Nikola Jokic who was taken 41st overall (the Raptors passed on him twice, as they selected Deandre Daniels at 37th overall).

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Joey Graham - 16th overall (2005)

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Toronto Raptors - Joey Graham. (Photo by Aaron Lynett/Toronto Star via Getty Images)

No discussion of Toronto Raptors draft day mistakes is complete without addressing the selection of Joey Graham. While he was not a total reach, he was not the top-rated player on the board. The fact that the Toronto Raptors had already passed on Danny Granger once only to still see him available at 16th overall and pass again is what makes the Graham selection such a colossal blunder.

Danny Granger went one pick later at 17th overall and turned into a dynamic small forward who could guard the two to the four. Granger had the type of range to become a perfect complement to then franchise player Chris Bosh. He maxed out as a 25.8 point per game scorer in the 2008-09 season. He made one All-Star appearance.

Graham did show some glimpses in his NBA career, but ultimately only ended up playing six seasons. Graham’s best game as a pro came on April 30th, 2010 as a member of the Denver Nuggets when he put up 21 points, 10 rebounds, a block, and two steals. Graham averaged just 6.4 points and 3.4 rebounds on 48-percent shooting as a member of the Toronto Raptors. He was never viewed as ready during his tenure and managed only 17.4 minutes per game. Graham lasted 275 games as a Raptor. He started 58 of them.

As alluded to above, Graham’s ranking here is as much about who the Raptors directly passed on as it is about the Graham selection itself. An undersized power forward who was forced to play small forward due to the depth chart, Graham never had the range or offensive basketball IQ to become anything more than an end of the bench player. He was a reach, but he was still a player expected to go in the mid to high teens. Just not before Danny Granger.

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Delon Wright - 20th overall (2015)

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Toronto Raptors - Delon Wright. (Photo by Issac Baldizon/NBAE via Getty Images)

Delon Wright was an interesting choice at 20th overall in the 2015 NBA Draft. He was long at 6-foot-5 and had more of a traditional point guard game then our starter at the time in Kyle Lowry. He profiled as being an ideal pick and roll point guard who could help unlock Jonas Valanciunas immense power offensive upside. Wright’s upside seemed limited to a high-end backup who would need to develop a consistent outside shot to become anything more.

Wright looked like he was going to be a key piece for the Raptors until the 2016-17 season when the Toronto Raptors signed an undrafted free agent point guard named Fred VanVleet. VanVleet was not as pure of a point guard, but had a superior range and was comfortable on the big stage after having made it to the final four with Wichita State.

The two would provide solid backup minutes behind, and sometimes spot starting for Kyle Lowry, but with Fred VanVleet being awarded a $9 million dollar per year deal before Wright was even done his rookie contract (four years because he was a first-round pick), it became clear that Wright was a luxury that was to be considered a potential asset. Wright would eventually be traded to the Memphis Grizzlies along with Jonas Valanciunas and C.J. Miles for former all-star Marc Gasol.

Wright averaged 6.7 points and 2.3 assists per game in his four seasons with the Toronto Raptors. Highlighting the stat sheet stuffing style that endeared him to Toronto fans, he averaged 12.4 points, 5.4 rebounds, and 5.6 assists in 30.6 minutes per game in his 26 games with the Memphis Grizzlies. Those numbers jumped to 14.5 points, 7.4 rebounds, 7.2 assists and 1.7 steals per game in his 13 starts for them. He is now a member of the Dallas Mavericks after joining them in free agency.

Wright was the correct selection at the time. In fact, the only players drafted after him that now look to have higher NBA ceilings were taken in the second round. One, Norman Powell was taken by the Toronto Raptors themselves. The other two are Montrezl Harrell of the Los Angeles Clippers and Josh Richardson of the Miami Heat.

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Jakob Poeltl - 9th overall (2016)

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Toronto Raptors - Jakob Poeltl. (Photo by Vaughn Ridley/Getty Images)

Stuck with the ninth pick in an eight-man draft, the Toronto Raptors went for upside. Poeltl averaged just 9 points and 7 rebounds in his final college season but did so in 26 minutes per game. Often referred to as an Austrian Andrew Bogut, Jakob has significant upside. His selection was a bit peculiar with Jonas Valaciunas on the roster. His addition signaled that the Raptors brass was not completely satisfied with the Lithuanian’s lack of development in certain areas.

In hindsight, there were some intriguing names on the board at ninth overall, but the best of them went to the Toronto Raptors 27th overall in Pascal Siakam. Eventual rookie of the year Malcolm Brogdon, Dejounte Murray, Taurean Prince, Caris LeVert, Ivica Zubac, and Domantas Sabonis were all still on the board at ninth overall.

Poeltl would spend only two seasons with the Toronto Raptors before being traded as part of a package for Kawhi Leonard and Danny Green in the summer of 2018. As a member of the Raptors Poeltl showed some flashes and at times looked like a better prospect than our starting center in Jonas Valanciunas. He was more of a traditional big, but he had the defensive and rebounding prowess to go with it.

Poeltl averaged 5.4 points and 4.6 rebounds in 15.8 minutes per game in 136 contests as a Toronto Raptor. Those numbers did not see much of a jump in 2018-19 as he was still utilized in a rotational role as a member of the San Antonio Spurs. He averaged 5.5 points, 5.3 rebounds in 16.5 minutes per game for San Antonio. He started 24 contests.

Poeltl’s career highs are as follows: 20 points, 14 rebounds, 6 assists, 5 blocks, 3 steals. Those numbers were all achieved in separate games but serve to accentuate his upside. Poeltl may very well make a giant leap up these rankings when we revisit them next summer.

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Terrence Ross - 8th overall (2012)

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Toronto Raptors - Terrence Ross. (Photo by Bruce Yeung/NBAE via Getty Images)

Terrence Ross was both one of the most exciting young players in Toronto Raptors history as well as one of their biggest draft mistakes ever. Ross was a good player and has a skill set that is sought after in today's NBA. He has yet to find that elusive consistency, but he is a slasher who can create for himself off the dribble and catch fire from deep. A former slam dunk champion, Ross tied Vince Carter’s single-game record of 52 points.

Despite his well-rounded game, high flying antics and perfect fit in today's NBA, he will always be remembered as the player Bryan Colangelo passed on Andre Drummond for. No one could believe the selection at the time as Ross wasn't even discussed as a lottery pick by most analysts. Drummond’s inexplicable slip to eighth overall seemed to signal the Toronto Raptors just had the steal of the draft fall into their laps. Alas, it was not to be.

Colangelo, who had designs on signing Steve Nash in free agency, believed that Ross would be an ideal fit next to Nash and DeRozan in the pace and space offense he wished to implement. He likely also questioned the fit of Drummond next to Jonas Valanciunas. Fast forward to free agency and Steve Nash ended up choosing the Los Angeles Lakers.

Ross would go on to average 9.5 points in his 363 games as a Toronto Raptor. Those numbers would spike to 13.4 points with 2.3 three-pointers per game in his time with the Orlando Magic. He had his best season in 2018-19 with 15.5 points and 2.7 threes made per game.

Drummond, however, would become one of the premier big men in the league and arguably the league's best rebounder. He made two all-star appearances and won three rebounding titles. He has averaged 14.1 points, 13.7 rebounds and 1.6 blocks on just under 55-percent shooting thus far in his NBA career.

Adding insult to injury, he had his best season under former a Toronto Raptors coach Dwane Casey. He averaged 17.3 points, 15.6 rebounds and 1.7 blocks on 53-percent shooting, numbers all the more impressive when one considers he did it beside an all-star level big in Blake Griffin.

Hindsight players the Toronto Raptors passed on include all-stars Draymond Green and Khris Middleton.

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Morris Peterson - 21st overall (2000)

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Toronto Raptors - Morris Peterson. (Photo by Joe Murphy/NBAE via Getty Images)

Morris Peterson is one of the Toronto Raptors all-time fan favourites. Selected at 21st overall, only seven players from the entire draft class would go on to play more total minutes than Peterson. Peterson was a key role player for the Toronto Raptors who averaged over 30 minutes per game in four of his seven seasons with the Raptors. He played both shooting guard and small forward and spent a considerable amount of time in the starting lineup.

Peterson topped out at 16.8 points in the 2003-04 season. He is remembered fondly by the Toronto Raptors fan base but shot under 44-percent every season of his career. He averaged 12 points on 42-percent shooting in 542 games with the Toronto Raptors. He is currently number two all-time in games played as a Toronto Raptor. ‘Mo Pete’ as he was known to Raptors fans is fourth all-time in minutes played, sixth in field goals, fifth in field goal attempts, and second in both three-pointers made and attempted.

The 2000 NBA Draft class was a deep class lacking any truly elite talents. Kenyon Martin was considered the only sure-fire All-Star of the class and Darius Miles was the high school sensation. The only notable player drafted after Peterson was Michael Redd. Redd went on to become a star in the NBA who averaged 19 points per game. His 55.9 win shares rank fourth in the class.

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Ed Davis - 13th overall (2010)

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Toronto Raptors - Ed Davis. (Jim Rassol/Sun Sentinel/MCT via Getty Images)

Ed Davis was a fantastic get for a Toronto Raptors franchise already reeling from the pending loss of Chris Bosh in free agency. The smooth shooting lefty big slipping to 13th overall seemed almost storybook.

Players like Patrick Patterson, Eric Bledsoe, Avery Bradley, Ekpe Udoh, and Hassan Whiteside were being considered by the Raptors at 13th overall as no one expected Ed Davis to still be on the board.

Davis averaged 7.7 points and 6.8 rebounds on just under 55-percent shooting in his 176 games with the Toronto Raptors. At his best as a Raptor in his rookie season, Davis logged 13 double-doubles. If not for a continuation of the Andrea Bargnani experiment, Davis likely would have had a much larger role for the Raptors.

He lasted under three seasons with the Raptors as they selected Centre Jonas Valanciunas in the 2012 NBA Draft making Davis more attractive as an asset. Davis was traded along with Jose Calderon to the Memphis Grizzlies for Rudy Gay. Davis would never surpass the 24.6 minutes per game he saw as a rookie.

He had his best NBA season at age 25 when he averaged 8.3 points and 7.6 rebounds and 1.2 blocks on 60-percent shooting for the Los Angeles Lakers. Davis is still a serviceable big man but has seen his days as a starter pass him by.

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Jonas Valanciunas - 5th overall (2011)

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Toronto Raptors - Jonas Valanciunas. (Photo by Harry How/Getty Images)

As talented of a player that Jonas Valanciunas was and turned out to be, he was a major reach at fifth overall. Bryan Colangelo would have been wise to trade down and proved once again that he was mistake-prone when given choices in the lottery. There have been seven all-stars from the 2011 NBA Draft class. Six of them were drafted after Jonas. The other names the Raptors were considering at the time include Kawhi Leonard, Kemba Walker, Enes Kanter, Brandon Knight, and Bismack Biyombo.

Jonas Valanciunas was a talented big man who never quite fit with the pre-2018-19 Kyle Lowry. He showed steady improvement throughout his NBA career, but only started to realize his potential following his trade to the Memphis Grizzlies. In his 470 games with the Toronto Raptors, Jonas averaged 11.8 points, 8.4 rebounds and 1.0 blocks on 56-percent shooting. His best season as a Raptor came in 2015-16 when he averaged 12.8 points, 9.1 rebounds and 1.3 blocks on 56-percent shooting.

Jonas was dealt along with Delon Wright and C.J. Miles for Marc Gasol. The ultimate payoff for the trade was an NBA Championship. However, Jonas went wild for a Memphis Grizzlies team missing prized rookie Jaren Jackson Jr., and averaged an elite 19.9 points, 10.7 rebounds, 1.6 blocks on 54.5-percent shooting in just 27.7 minutes per game.

As mentioned above, Jonas being a reach who was drafted before all-stars who were also on the Raptors radar makes his selection a bad one. The Raptors had more pressing needs at the time at both point guard and small forward. The six all-stars drafted after Jonas were Kawhi Leonard, Kemba Walker, Klay Thompson, Jimmy Butler, Nikola Vuvecic and Isaiah Thomas. Tobias Harris was also still available.

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Charlie Villanueva - 7th overall (2005)

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Toronto Raptors - Charlie Villanueva. (Photo by Fernando Medina/NBAE via Getty Images)

Charlie Villanueva was a head-scratching pick at the time as he profiled at his best as an NBA power forward, the position Chris Bosh played. Charlie V proved to be able to man the three, four, and five and gave the Toronto Raptors tremendous length and versatility.

He would go on to become the third Toronto Raptor to win rookie of the year honours after averaging 13 points and 6.4 rebounds with 0.9 threes, 0.7 steals and 0.8 blocks per game on over 46-percent shooting. He set Toronto Raptor rookie records with 48 points on March 26, 2006, and 16 rebounds on April 2nd, 2006.

He was a great fit beside Chris Bosh as a stretch big, and it is possible that his success with Bosh made Bryan Colangelo believe that Andrea Bargnani would be a seamless fit in the same role. His presence on the roster made the Bargnani selection all the more confusing as Villanueva would have been perfectly capable of playing the three beside LaMarcus Aldridge and Chris Bosh.

Charlie V’s ascension to possible supporting role stardom was halted following the 2006 NBA Draft when he was traded for an important piece in point guard T.J. Ford. With the Toronto Raptors adding Andrea Bargnani, there was no space for Charlie Villanueva as Andrea Bargnani was essentially a poor man version of him. Villanueva had moderate success for the duration of his NBA career but never matched the 29.1 minutes per game that he saw as a rookie.

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OG Anunoby - 23rd overall (2017)

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Toronto Raptors - OG Anunoby. (Photo by Vaughn Ridley/Getty Images)

Ranked here due to value, OG was a lottery talent who slipped in the draft due to torn ACL. A versatile wing defender with a developing shot, OG was and is viewed as someone who can guard the one through the five.

“Obviously if he doesn't have that injury, I don't think we have a shot," said Raptors president Masai Ujiri.

Selected with the Toronto Raptors second first-round pick of 2017, the Raptors chose Anunoby with the first they acquired from Milwaukee (along with Norman Powell’s draft rights) in exchange for Greivis Vasquez.

Anunoby just turned 22 in July. He is the same age as Atlanta Hawks fifth overall pick Deandre Hunter (whose 22nd birthday falls this December) and Memphis Grizzlies 21st overall pick Brandon Clarke. Entering his third season and still the same age as some rookies, the book has yet to be written on the talented wing.

Anunoby has averaged just 6.4 points per game on 46-percent shooting to this point in his career but was still deemed untouchable in trade talks for Kawhi Leonard and Bradley Beal. Anunoby has steadily improved as both on offense and as a defender in his short NBA career. He has already made a name as one of the NBA’s best young defenders.

He has shown flashes on offense and aside from three-pointers made in a game, posted all of his career highs this past season. His six three-pointers made came against the Hornets on December 20, 2017. His other career-high numbers read as follows: 22 points against the Wizards, eight rebounds multiple times, three assists and three steals on three separate occasions, and two blocks twice.

Anunoby is projected to see a major role increase during this upcoming season, and depending on the development of Stanley Johnson, could soak up the majority of the minutes at the two or the three. Anunoby is likely to remain untouchable in the trade talks that will occur throughout the offseason and regular season.

Anunoby was a great pick by the Toronto Raptors and should continue to pay dividends over the next five to six seasons. There were no names that Raptors missed on in selecting Anunoby as he was the best talent available at the time. The most notable players to be drafted after OG include Kyle Kuzma, Josh Hart, and Jordan Bell.

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Pascal Siakam - 27th overall (2016)

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Toronto Raptors - Pascal Siakam. (Photo by Chris Elise/NBAE via Getty Images)

Finding someone who can average 19.0 points and 7.1 rebounds per game in the NBA Playoffs at 27th overall takes something special as far as player evaluation is concerned. It is harder to rank a player on a list like this who has yet to make it past his first contract as you are forced to do a lot of projecting.

Siakam’s current career path, especially with the Toronto Raptors roster as it currently stands, suggests that ‘Spicy P’ will be an NBA all-star as soon as this upcoming season. While we will see later that even Masai Ujiri can miss on non-lottery picks, Siakam was a gem of a find that Masai’s involvement with basketball without borders on the continent of Africa helped produce.

Siakam was a key player for the Toronto Raptors during their NBA championship season and carried the load at times during the regular season when Kawhi Leonard stayed on the sidelines due to load management. The most improved player this past season, Siakam is set to make a massive leap in 2019-20 for a Raptors team that lost its top player to free agency.

Siakam impressed with averages of 16.9 points and 6.9 rebounds on just under 55-percent shooting. He even developed three-point range. He is not exactly money from distance, but he managed to shoot at a decent 37-percent clip. After averaging 11.9 field goal attempts per game in 2018-19, Siakam could see that number jump to over 17 this upcoming season.

Siakam was an outstanding pick at 27th overall, but it is still worth noting that the 2016-17 rookie of the year in Malcolm Brogdon was drafted nine slots later. Pascal projects to be one of three players from the 2016 draft class to make an all-star appearance (along with current all-star Ben Simmons and eventual all-star Jamal Murray).

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Damon Stoudamire - 7th overall (1995)

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Toronto Raptors - Damon Stoudamire. (Photo by Nathaniel S. Butler/NBAE via Getty Images)

The sixth-best prospect in a six-man draft, Damon Stoudamire thankfully slipped to seventh overall due to the Vancouver Grizzlies franchise-altering decision to take Bryant ‘Big Country’ Reeves over the eventual rookie of the year. The top five picks in this class were Joe Smith, Antonio McDeyess, Jerry Stackhouse, Rasheed Wallace, and Kevin Garnett.

Damon Stoudamire went on to win the rookie of the year award by averaging 19 points, 9.3 assists, 4 rebounds, and 1.7 steals on under 43-percent shooting. Dubbed Mighty Mouse due to his diminutive stature in NBA terms, Damon Stoudamire was the franchises first and only star during the inaugural season.

He would spend only two and a half seasons in Toronto before demanding a trade. During his time with the Raptors he averaged 19.6 points, 8.6 assists, 4.1 rebounds and 1.5 steals on 41-percent shooting. The shooting numbers are atrocious, but for a Raptors team devoid of any other stars, this was not an issue for the fanbase or the organization.

Damon Stoudamire wanted out and was dealt to the Portland Trailblazers. If you ask the casual fan what Toronto received for Damon most would say Kenny Anderson, a player who refused to report to the Raptors. However, the full trade was Damon Stoudamire, Carlos Rogers, and Walt Williams for former all-star Kenny Anderson, Alvin Williams, Gary Trent, and two first-round picks. Kenny Anderson was then traded along with Popeye Jones, and Zan Tabak for future NBA Finals MVP Chauncey Billups, Dee Brown, Roy Rogers, and John Thomas.

His numbers would fall sharply once he left the Raptors due to playing with other stars, and thus receiving fewer shots per game. He managed to average 8.2 assists during the season he was traded but saw his number tail off from there. He averaged 12.8 points, 3.5 rebounds and 5.7 assists on 40-percent shooting in his eight seasons with the Portland Trailblazers. He would never shoot above 43.6-percent in his career.

In Memphis, he was employed in more of a mentorship role in 118 games with them. He started most of the games he played but averaged just 25.3 minutes per game. Damon averaged just 8.4 points and 4.6 assists on 39-percent shooting in those 118 games. Damon took a young point guard by the name of Kyle Lowry under his wing in Memphis and is one of the players Kyle credits with helping propel his career. This was the reason Kyle wore his jersey during the Toronto Raptors NBA Championship parade.

The most significant player the Raptors passed on was Michael Finley who ended up going 21st overall to Phoenix. Damon was the right call at the time as he was sensational in his short time with the Raptors. In hindsight, Finley had the better career and ‘Mighty Mouse’ ended up asking for a trade before his first contract was over.

You can still find his name attached to numerous Toronto Raptors career leaderboards. He ranks first in minutes per game, fifth in assists, fourth in points per game, first in assists per game, second in steals per game, and third in assist percentage. Damon would be higher on this list if we just judged his production and impact as a member of the Toronto Raptors.

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Chris Bosh - 4th overall (2003)

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Toronto Raptors - Chris Bosh. (Photo by Jesse D. Garrabrant/NBAE via Getty Images)

One of the most controversial Toronto Raptors draft picks of all time went on to become one of the Toronto Raptors best players through their first 24 years of existence. This pick was controversial for two reasons. The main reason was that Vince Carter directly requested that the Raptors trade the pick for a veteran that could help a Raptors team that was looking to make a deeper playoff run. Chris Bosh was rail-thin when he entered the league, and while skilled, he was not ready to be a steady contributor to a playoff team.

The second cause for controversy was that if the Raptors did indeed intend to keep the draft pick, there was an NBA ready combo guard out of Marquette that fit the Toronto Raptors roster beautifully. The Raptors had been searching for an answer at the point since Damon Stoudamire left town, and Wade had the skills to be an excellent scoring point guard or off-ball complement to Vince Carter.

Bosh was viewed by the consensus as the superior prospect and went fourth overall after workout warrior Darko Milicic soared to number two overall. As pointed out here, not drafting Wade started a domino effect that had a direct correlation to Vince Carter finally having enough and requesting a trade.

Chris Bosh himself blossomed into the player it was hoped he would be when he was drafted. There was even a time when some would have argued (wrongly of course) that Chris Bosh was the greatest Raptor of all-time.

During his time as a Toronto Raptor, Bosh averaged a robust 20.2 points and 9.4 rebounds on 49-percent shooting and led the Raptors to their first-ever division title. He had the best season of his career in his contract year when he averaged 24 points and 10.8 rebounds on just under 52-percent shooting.

‘CB4’ is still among the Raptors career leaders in a number of categories. He leads the team in rebounds, rebounds per game, and total blocks. He ranks in the top three in field goals, PER, win shares, value over replacement, points, points per game, minutes per game, and free throws. The best power forward in Raptors history, Chris Bosh was one of the faces on the Toronto Raptors Mt. Rushmore prior to the 2018-19 season.

While the fanbases animosity towards him has somewhat thawed over the years, the vitriol towards him is still the strongest among stars who departed the Toronto Raptors.

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DeMar DeRozan - 9th overall (2009)

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Toronto Raptors - DeMar DeRozan. (Photo by Noah Graham/NBAE via Getty Images)

With no first-round selections being added to the roster for two straight seasons, Bryan Colangelo seemed to have finally figured out drafting in the lottery. DeMar DeRozan was the no-brainer selection after he slipped past the New York Knicks and made it to ninth overall. An athletic shooting guard who garnered Kobe Bryant comparisons in high school, DeRozan was the Toronto Raptors top draft talent since Chris Bosh.

DeRozan became an instant fan favourite due to his above the rim action and gave the Raptors their most exciting prospect since Vince Carter. DeRozan became widely regarded as the greatest Toronto Raptor of all-time prior to the 2018-19 season. This was largely due to his willingness as an all-star to stay past his second contract as opposed to being an illustration of his incomparable talent. This was something that had never happened with our previous all-star level players and helped further endear him to a fanbase who had still not come all the way around on Vince Carter.

With DeRozan deemed unlikely to be there at ninth overall, there were some interesting talents the Raptors were considering including Terrance Williams, James Johnson and Earl Clark. All three players failed to live up to their immense upsides. The top talents to come off of the board after DeRozan were former all-star point guards Jrue Holiday and Jeff Teague.

With Chris Bosh still on the team during his rookie season, DeRozan had a slower start to his career despite being force-fed minutes. He averaged just 8.6 points per game. He maxed out as a 27.3 points, 5.3 rebounds and 3.9 rebounds on just under 47-percent shooting during the 2016-17 season. DeRozan averaged 19.7 points over his nine-year career as a Toronto Raptor.

As most may know trading the all-time fan favourite led to the Toronto Raptors acquiring one of the best players in the world in Kawhi Leonard. Kawhi helped lead the Raptors to an NBA Championship. DeRozan for his part went on to have what could be argued is the best season of his career by averaging 21.2 points, 6.0 rebounds, and 6.2 assists on 48-percent shooting. He operated as the team's primary ball-handler and truly took his game to another level.

The 48.1-percent shooting was his best clip since his rookie season when he averaged under seven shots a game. The rebounds and assists are both career highs. DeRozan should see his number raised to the Raptors rafters when all is said and done. DeRozan would be higher on this list if it were not for the fact that he was a no-brainer selection, and is and was never as talented as the two Hall of Fame names on this list were.

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Marcus Camby - 2nd overall (1996)

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Toronto Raptors - Marcus Camby. (Photo by Nathaniel S. Butler/NBAE via Getty Images)

The Toronto Raptors won the draft lottery in 1996 but were unable to claim first overall due to an agreement the Raptors made with the NBA upon receiving an expansion franchise. That meant the Toronto Raptors were unable to acquire the services of the consensus number one overall pick and one of the NBA’s greatest scorers of all-time in Allen Iverson.

Camby had a stellar NBA career even if it was marred by incessant injuries. He was a four-time All-NBA Defensive team selection, won four block titles, and won the Defensive Player of the Year award in 2006-07 at age 32. He would play in the league for 18 years but saw over 70 games just three times.

As a member of the Toronto Raptors Camby averaged 13.5 points, 6.8 rebounds, 1.1 steals and 2.9 blocks on just under 45-percent shooting. He started 96 of his 126 games as a member of the Toronto Raptors. His 2.9 blocks per game average as a Toronto Raptor stands to this day and is likely the one team record that will never be broken.

Marcus Camby would eventually be traded for Charles Oakley, Sean Marks, cash and a second-round pick. The NY Times suggested the move could have been at least partially financially motivated. The Raptors were said to be fearful of their prospects of retaining Marcus Camby when he hit free agency the following year.

As a member of the New York Knicks Camby averaged 9.3 points, 8.6 rebounds and 1.8 blocks on 49-percent shooting in 26.6 minutes per game. He started only 107 of the 221 games he played with them due to the presence of players like Patrick Ewing and Larry Johnson.

Camby would go on to truly shine as a member of the Denver Nuggets. He averaged 10.1 points, 11.1 rebounds, 1.1 steals and 3.0 blocks per game on just over 46-percent shooting in 31.7 minutes per game. He started 350 of his 372 games with the Nuggets.

The best season of his career came as a Nugget when he averaged 12.8 points, 11.9 rebounds, 1.4 steals and 3.3 blocks on over 46-percent shooting during the 2005-06 season. Camby would spend time with the Los Angeles Clippers, Portland Trail Blazers, and Houston Rockets before retiring as a member of the New York Knicks in 2012-13.

The 1996 draft was a loaded one, but those old enough to remember will recall that Marcus Camby was the correct pick at the time. Camby was a dominant big at both ends of the court, and bigs were viewed with a much bigger premium in the Shaquille O’Neal era.

Significant players the Raptors passed on include Kobe Bryant, Ray Allen, Jermaine O’Neal, Steve Nash, and Stephon Marbury. Players like Antoine Walker, Peja Stojakovic, Kerry Kittles, Derek Fisher, and Jerome ‘JYD’ Williams were also in this draft but were not prospects that a team would consider as high as number two overall.

Marcus Camby was one of the best Raptors draft picks of all-time talent-wise, but the names that went after him keep him lower on this ranking than he would otherwise find himself.

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Tracy McGrady - 9th overall (1997)

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Toronto Raptors - Tracy McGrady. Mandatory Credit: Craig Jones /Allsport

Hall of Fame. Two-time scoring champion. Seven-time all-star. Seven-time All-NBA. 2000-2001's  Most Improved Player. Arguably the best draft pick in Toronto Raptors history.

McGrady averaged 11.1 points and 5.5 rebounds on just under 45-percent shooting in 24.7 minutes per game in his three seasons with the Raptors. He started only 53 of the 192 games he played with the Toronto Raptors. T-Mac averaged 15.4 points, 6.3 rebounds and 3.3 assists on 45-percent shooting in 31.2 minutes per game in his final season with the Raptors, but was still only allowed to start 34 of his 79 contests due to the presence of defensive stopper Doug Christie.

Tracy McGrady heartbreakingly left the Toronto Raptors in 2001 to be the star of own team. He joined forces with a post-injury Grant Hill in what some (such as Rob Parker on his Odd Couple radio show last week) point to as the first example of multiple free agents conspiring to play together in a specific city.

T-Mac has frequently cited cable (pre-streaming and IPTV days) and taxes as two of the hardest parts of playing in Toronto. Doug Christie starting over him while his cousin shined at small forward may have played a correlative factor as well. The Raptors knew he was going to walk and explored trades throughout the season most notably (at the time) for Larry Hughes.

T-Mac would go on to have a Hall of Fame career for the Orlando Magic and the Houston Rockets before recurring back issues cut his career short. He was at his statistical best as a member of the Magic where he averaged 28.1 points, 7.0 rebounds, 5.2 assists, 1.5 steals and a block per game over 295 contests. His best season came in 2002-03 when he averaged an amazing 32.1 points, 6.5 rebounds, and 5.5 assists on just under 45-percent shooting. The shooting percentage was the high watermark for his career.

T-Mac was at his best however as a member of the Houston Rockets where he remained dominant despite sharing the scoring load with Yao Ming. As a Rocket, he averaged 22.5 points, 5.5 rebounds, and 5.6 assists. His best season as a Rocket came in 2006-07 when he averaged 24.6 points, 5.3 rebounds and 6.5 assists on 43-percent shooting.

The first high school player taken in the 1997 NBA Draft, Tracy McGrady was a fantastic pick by the Toronto Raptors. There were no significant players taken behind him and it was exciting that the Raptors were willing to go the high risk/high reward route as opposed to going with a safe pick.

The most notable players to be drafted after the Hall of Famer were former Raptors Alvin Williams and Anthony Parker, and former NBA Champion Stephen Jackson. Jackson and Williams were both second-round picks.

McGrady was the right pick then and in retrospect was an absolute steal. He is one of only two players from that class currently in the hall of fame. T-Mac would be higher on this list if he played more than just three seasons with the Toronto Raptors or shot at a higher percentage over the course of his career.

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Vince Carter - 5th overall (1998)

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Toronto Raptors - Vince Carter.

Half-Man, Half-Amazing. Air Canada. Eight-time all-star. Two-time All-NBA. 1998-99 rookie of the year. Owner of the best slam dunk contest performance of all-time.

Vince Carter changed everything. As anyone who has taken in the documentary the Carter Effect will know, Vince Carter changed how basketball was viewed in Toronto and the country of Canada single-handedly.

Yes, we know Carter wasn't technically drafted by the Toronto Raptors. However, for all intents and purposes, it was Toronto making the call.

One of the most exciting players in the league as a mere rookie, Carter was in the conversation for best player in the league during his time with the Raptors. Players like Allen Iverson, Kobe Bryant, Shaquille O’Neal, and ex-teammate and cousin Tracy McGrady prevented him from ever claiming that title.

As naturally gifted and talented as any player in the NBA, Carter was dogged with effort questions during the tail end of his Raptors tenure. Being nice and friendly with his opponents is something that was new to the NBA at the time, and was not something those from the old school looked upon too kindly. His run with the Raptors was a tumultuous one, but it was not without its highs.

The Toronto Raptors were one shot away from advancing to the Eastern Conference finals for an easy date with an overmatched Milwaukee Bucks team. His performance in the slam dunk contest created Toronto Raptors fans not only across Canada but south of the border as well. Kevin Durant famously admitted that he was a Toronto Raptors fan and wanted to play for them growing up because of Vince Carter.

His impact extends beyond the all-star appearances, his work in the community, or his business. He influenced multiple generations of young Canadians to take basketball more seriously for either themselves or their children, in some cases both. He is directly responsible for the explosion of Canadian talent in the NBA. In fact, he is part of the reason the NBA still exists in Canada.

As for the basketball itself, when he was committed to being at his best, he was sublime. In his rookie of the year campaign averaged 18.3 points, 5.7 rebounds, 3.0 assists, 1.1 steals and 1.5 blocks on 45-percent shooting. He went on to average 23.4 points, 5.2 rebounds, 3.9 assists, 1.3 steals, and a block per game on 45-percent shooting in his seven seasons as a Toronto Raptor. His best season in Toronto came in 2000-01 when he averaged 27.6 points, 5.5 rebounds, 3.9 assists, 1.5 steals and 1.1 blocks on 46-percent shooting.

Repeated questionable personnel decisions by the Toronto Raptors played a correlative effect in leading Vince Carter to ask out of Toronto. The divorce was an ugly one that ultimately made Vince Carter the fanbases most hated man for over a decade. The return in the trade did not help matters and only served to exacerbate the situation.

Vince Carter, a day after going to Rob Babcock in an effort to make things work with the team was dumped for Alonzo Mourning (who the team intended to buyout immediately), Eric Williams, Aaron Williams, and two first-round picks. The New Jersey Nets got a motivated Vince.

The best stretch of his career came during the season of the trade when he averaged 27.5 points, 5.7 rebounds, 4.7 assists, 1.5 steals and 0.6 blocks on 46-percent shooting in the 57 games he played with the Nets.

Vince would have some of the best seasons of his career in New Jersey as he averaged 23.6 points, 5.8 rebounds, and 4.7 assists on 44-percent shooting in 374 games as a member of the Nets.

Vince Carter would go on to spend three seasons with the Dallas Mavericks, three seasons with the Memphis Grizzlies, two seasons with Orlando Magic. He also spent a year with the Phoenix Suns, Sacramento Kings and most recently the Atlanta Hawks. When Vince Carter plays his first game next season he will set a new record for the most seasons played in the NBA.

The 1998-99 draft class produced three Hall of Famers in Dirk Nowitzki, Paul Pierce, and Vince Carter. Both Dirk and Pierce were selected after Vince Carter. Vince was the better prospect, but due to winning NBA championships, both Pierce and Nowitzki went on to have more storied careers. Vince was a steal based on the four names that went ahead of him. Michael Olawakandi, Mike Bibby, Raef Lafrentz and Antawn Jamison.

Next: 30 greatest players in Raptors history

Vince Carter slightly edges out Tracy McGrady for the top spot on this list due to his talent and impact on Toronto basketball. Some may argue that McGrady was the better player and in many respects, they would be right.