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Josh Lewenberg

TSN Raptors Reporter

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TORONTO – Even in the most unusual of circumstances, the Toronto Raptors are confident that they’ll be able to find another hidden gem or two in this week’s NBA draft – or in the weeks to follow – and, given their recent track record, it’s not hard to see why.

Since arriving in 2013, the front office team of Masai Ujiri, capologist-turned-general manager Bobby Webster, and scout-turned-assistant GM Dan Tolzman – with contributions from many others – has earned its reputation. The Raptors are widely regarded as one of the NBA’s premier clubs at finding and developing young talent.

Together, that group has made seven picks over a seven-year span, including five first-round selections, with only one of them coming inside the top-20. However, it hasn’t mattered where they’ve drafted from, or even if they’ve had a pick at all.

Through the draft process, they’ve unearthed seven NBA rotation players, including an unlikely all-star and franchise cornerstone. Four of those players would become part of their championship core, and another two were used to acquire crucial veteran pieces that put them over the top during the team’s title-winning season.

The Raptors own the 29th and 59th overall picks in this year’s draft, which will be held virtually on Wednesday.

Historically, they’re not an organization that tends to reveal much leading up to the draft, and without being able to conduct their own workouts with this crop of prospects – thanks to the league’s pandemic restrictions – we have even less to go on than usual.

So, what does their success on and around draft night, as well as the type of prospects they’ve gravitated to in the past, tell us about how they might approach their upcoming selections?

In terms of risk tolerance, Ujiri’s Raptors have been a mixed bag.

They’ve shown they’re not afraid to roll the dice and gamble on upside – to varying results – especially late in the first round.

Bruno Caboclo – the first player they drafted in Toronto – has become the face of that strategy. They didn’t just go off the board to take him 20th-overall in 2014, they made the mysterious Brazilian product one of the most out-of-nowhere picks in modern history. Many professional scouts and league executives didn’t even know who he when the commissioner read – and mispronounced – his name. On the broadcast, Fran Fraschilla famously opined that he was “two years away from being two years away”.

The Raptors knew that, though, and they were okay with it. Understanding that very few picks in that range actually hit, why not take a big swing?

They were willing to bet on Caboclo’s potential and on their player development program, and even though it didn’t work out, it remains a justifiable gamble. Why? Because of what happens when one of those big swings connect.

Toronto hit a home run with the 27th pick in 2016.

Unlike Caboclo, Pascal Siakam was on the draft radar, but most mocks had him falling to the second round. Even in their most optimistic projections, the Raptors couldn’t have expected him to blossom into an all-star and max contract player, but with some G League seasoning they believed he was a future NBA starter.

As a winning club selecting towards the bottom of the first round, there’s less pressure to hit on every pick than there is for a lottery team. A Caboclo-type player isn’t going to sink you, but a Siakam-type – as hard as they are to find – can extend your competitive window. That’s the philosophy that helped the Spurs find diamonds in the rough, Manu Ginobili (the 57th pick in 1999) and Tony Parker (the 28th pick in 2001), and sustain their run of success for more than two decades.

However, as a winning club with a top-heavy salary structure, there is some pressure to build through the draft – filling out the backend of your rotation with young and inexpensive talent that can be developed over time. Few teams have done that better than the Raptors, but the biggest misconception about their front office is that they’ve done it by swinging for the fences. They’ve also shown a willingness to play it safe, when the situation has called for it.

At ninth-overall in 2016 – the team’s lone lottery selection of this era, a gift from the Knicks via the Andrea Bargnani trade – Jakob Poeltl was considered more of a conservative pick, as was his college teammate Delon Wright, who Toronto took 20th the year prior.

Neither pick seemed shocking at the time – Wright was projected to go somewhere in the 20s and most pundits had Poeltl coming off the board late in the lottery. They were both expected to contribute right away and go on to have solid NBA careers, but many predicted that age and skill set would limit their upside – and, so far, that assessment has mostly rung true. Still, Poeltl and Wright were important rotation pieces with the Raptors for years before being included in the deals that landed Kawhi Leonard and Marc Gasol, respectively, in Toronto.

You can see the Raptors taking either approach this year, particularly with the 29th pick.

On one hand, they have an eye on the future with aspirations of competing for another championship, perhaps as early as 2021. It might make sense to take a player who fits that timeline and needs a year or two to develop. Maybe this is the year to pick somebody they can stash overseas.

On the other hand, assuming they plan to remain competitive this season, they’ve got a few holes to fill. Their two centres, Marc Gasol and Serge Ibaka, are about to hit unrestricted free agency – and Chris Boucher will be restricted – and while they hope to retain at least one, they could certainly use another young body in the frontcourt. With Fred VanVleet also headed for free agency, and Kyle Lowry turning 35 in March, they’re in need of some insurance at the point guard position. Then, depending on what they decide to do with Terence Davis’ team option for next season, they could also consider adding more depth on the wing.

All of that is to say, you could understand why they might opt for a more seasoned rookie that could step in and make an immediate impact.

Although their approach has fluctuated over the years, there are some common denominators among the players they’ve selected. Admittedly there are skills and qualities they look for in draft prospects.

The Raptors have prioritized length, athleticism and defensive versatility, with the belief that some of the more foundational skills like shooting or playmaking can be developed over time. Their most recent first-round pick, OG Anunoby, fits that bill perfectly.

A projected lottery pick in 2017, Anunoby fell to Toronto at 23 after teams were scared off by the knee injury that threatened to delay the start of his rookie campaign. CBSSports.com called it a “risky pick” but went on to say that Anunoby could be “the Draymond Green of this draft.” Much of that intrigue, and the Green comparison, were based on his NBA ready frame, 7-2 wingspan and defensive acumen.

Norman Powell (6-11 wingspan) – who was acquired after being taken in the second round of the 2015 draft – Siakam (7-3 wingspan) and even Caboclo (a massive 7-7 wingspan) checked off a lot of those boxes, as well.

They also value things like basketball intellect, work ethic, character and drive – qualities that have helped make VanVleet one of the greatest undrafted success stories in league history.

While this isn’t a top-heavy draft, it’s believed to be a deep one, which could play into the Raptors’ strengths. There should be several players that fit their criteria available at 29, and perhaps even at 59 or in the undrafted market, where they’ve also thrived.

If they’re looking for a more NBA-ready prospect, TCU senior Desmond Bane seems like the type of high-IQ, high-character wing that would fit right in. They could also consider point guards Payton Pritchard (Oregon), Tre Jones (Duke), Cassius Winston (Michigan State) and Malachi Flynn (San Diego State), or bigs Paul Reed (DePaul) and Xavier Tillman (Michigan State).

If they opt to take a high-upside flier, they could be intrigued by the 7-foot-4 wingspan of Washington big man Isaiah Stewart, the motor of Maryland big Jalen Smith, the skills of bigs Zeke Nnaji (Arizona) and Jaden McDaniels (Washington), or the speed and smarts of guards Nico Mannion (Arizona) or Devon Dotson (Kansas).

Or, maybe they’ll go off the board and surprise us all again.​