5 worst draft mistakes in Toronto Raptors franchise history

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In about a month from now, the NBA will be holding its annual draft lottery.  A time of hope for the league’s most broken and beaten down franchises, a time of prayer as the basketball gods decide who will rise and who will fall, and a time for the Toronto Raptors to get their due for playing in Tampa all year.

This year’s draft lottery has a strong top-five and a solid 6-15, but every team within striking distance is hoping that they can move into those first top slots. The Raptors would need a little luck to get there (they have the 7th odds), but far crazier things have happened on lottery night.  Just last year the Charlotte Hornets moved from 7 to 3 and landed LaMelo Ball.

Wherever the pick lands, the Raptors will have to make the right selection with it. Masai Ujiri has long been reputed as one of the best general managers in the sport, but as far as high lottery picks go he’s fairly untested.

Masai has actually had more success picking in the late first-round than up top, and while his time with the Raptors has seen more success and therefore more late first-round picks, he’s yet to hit a home run with a lottery selection.

Between DeMar DeRozan in ’09, a gift-wrapped trade for Vince Carter, a lucky hit on a springy high schooler named Tracy McGrady, and a no-brainer fourth overall selection in Chris Bosh, and the Raptors draft history has been pretty spotty. Besides those four guys, the Raptors’ higher draft picks have been pretty weak.

Let’s quickly recap some of these tremendous flops on draft night. Granted, many of these were before Masai’s time as Raptors President, but they still stink.

Top 5 worst mistakes in Toronto Raptors draft history.

Jonathan Bender, Toronto Raptors

AUBURN HILLS, MI – JUNE 1: Ben Wallace #3 of the Detroit Pistons attempts to rebound over Jermaine O’Neal #7 and Jonathan Bender #24 of the Indiana Pacers (Photo by Ezra Shaw/Getty Images)

1999 NBA Draft:  Jonathan Bender (No. 5 pick)

This move is a little complicated, and calling it a draft mistake is a little controversial, but let’s just break down the history real quick, and then you can decide for yourself.

This late 90s-early 2000s stretch was a truly silly time in NBA draft history. With an influx of international talent, high schoolers like Kevin Garnett coming in and contributing right away, and players hopping from college to the pros faster, the knockout swings teams were taking on big-time hit-or-miss prospects was astounding.

Bender was taken out of high school as a 6-11 freak athlete at the wing position. Because of the wing talent Toronto already had in Carter and McGrady, it came as no surprise to anybody when Bender was immediately traded to the Indiana Pacers in exchange for Antonio Davis, a one-time all-star for the Raps and a solid second option during the prime Vince Carter years.

So why is this a mistake?

Bender was picked in a draft year that had no all-time greats to offer, but a huge swath of lower to mid-level future all-stars.  Bender was taken fifth, and the next few picks looked like this:

6) Timberwolves:  Wally Szczerbiak
7) Wizards:  Richard Hamilton
8) Cavaliers:  Andre Miller
9) Suns:  Shawn Marion
10) Hawks:  Jason Terry

Davis was nice, but I would have rather had any one of those guys as a running buddy for Vince. Part of why Carter left the Raptors was because he saw no help in sight after an older Davis started to decline in the mid-2000s.

If he had had a running mate like Shawn Marion or Rip Hamilton, another young star to grow with and play off of, maybe the Carter era would’ve been longer and more successful.

This isn’t so much a mistake as a missed opportunity. Davis was no slouch, he was a good big man and a valuable Raptor, but when you have a chance to build a young core of Carter, McGrady, and Marion, Terry, or Miller, it’s hard not to be a little bummed out.

The Raps spent the 12th pick in this draft Bosnia’s Aleksandar Radojevic, who plated just 15 NBA games and 3 with Toronto. instead of Corey Maggette (13th) or Ron Artest (16th). Fun.