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How far should the Raptors go to retain Fred VanVleet?

Midway through the 2019-2020 NBA season, the Toronto Raptors were faced with a decision. Should they be trade deadline buyers, and go all-in on contending for another championship? Or should they be trade deadline sellers, with veterans such as Marc Gasol, Fred VanVleet, and Serge Ibaka all set to hit free agency in the summer, whereby the Raptors would risk losing them for nothing?

Ultimately, Masai Ujiri and Bobby Webster, Toronto’s President and General Manager respectively, decided to choose neither path. They stayed pat, and gave their core of VanVleet, Kyle Lowry, Pascal Siakam, and OG Anunoby another opportunity to bring gold to Canada – an opportunity that they had earned as defending champs, which was reinforced by how well they had played all regular season long.

And while Ujiri’s and Webster’s decisions back at the trade deadline in February may have been the correct ones, the Toronto Raptors were eliminated by the Boston Celtics in the second round of this year’s playoffs, and have been sitting at home ever since. Could the Raptors have repeated this season with their current roster construction if they had just shot the ball a little bit better? Absolutely. But they didn’t, and now, tough decisions loom once again.

By opting to keep Gasol, VanVleet, and Ibaka all on the roster, Toronto set themselves up for a free agent frenzy in the summer – or winter rather, because of the prolonged NBA season. Toronto’s front office gurus have been back to work after enjoying a few weeks down in Florida. Out of their three marquee free agents, who should they be willing to let go of, who should they be looking to retain, and at what price?

I’ve already delved deep into some analysis on the Raptors situation at the centre slot, regarding Ibaka, Gasol, Chris Boucher, and another under-the-radar free agent target that the Raptors are rumoured to have some interest in. When it comes to Fred VanVleet however, the criteria becomes slightly trickier.

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VanVleet’s career story is well known. He placed a massive bet on himself, and it paid off. He’s one of the most beloved players in Toronto Raptors franchise history, and is certainly one of the best too, but his shortcomings are glaring – especially after this year’s playoff run.

Despite being one of the Raptors best big-shot makers and steadiest three-point shooters, his game can only be marveled at in some categories. Standing at just six feet tall, Freddy’s bulky 195 pound frame gives him some ground, however it’s hard for him to match up with some of the bigger shooting guards in the NBA defensively. He’s still able to provide a plus on that side of the basketball with his quick hands – which were good for getting him 1.9 steals per game this season – although much of that is due to his ability to gamble in passing lanes because of how quick the Raptors rotations are.

Nevertheless, all of this is not to say that VanVleet is a weak defender. Last year in the NBA Finals, he drew the tough assignment of guarding Stephen Curry, and did an excellent job of bothering Curry’s shot attempts to the point where he was rendered a lesser offensive threat. It merely goes to show that VanVleet has shortcomings on that end of the floor due to his size, which can’t necessarily be improved upon.

Offensively, VanVleet’s frame holds him back too, but again, it’s not nearly all negatives on that side of the ball. Almost always matched up with a bigger and quicker opponent, VanVleet relies on his tight handle to work his way into the paint. According to NBA.com, he actually led the Raptors in drives per game this season at 14.3, which was invaluable in creating offensive flow for a team that otherwise had very little. He also makes smart decisions with the basketball once he does find his way inside, kicking out on 57% of his drives – one reason why he averaged a career-high 6.6 assists per game this season. He also passes out quite efficiently, ranking near the top of the league in assist-to-turnover ratio, at 3.0.

VanVleet’s biggest inefficiencies on offense stem from the 43% of the time that he opts not to kick the ball out of the paint. As the smallest player on the floor, opposing big men lurking around the rim have a wide margin for error when it comes to swatting VanVleet’s layup attempts into the fourth row of the stands.

Though Freddy is one of the best shooters in the league from outside the arc, making good on 39.0% of his 6.9 three-point attempts per game, his field goal percentage inside the perimeter is below average. A majority of Freddy’s two-point shots come in the paint, where he ranked right at the bottom of the league in efficiency this year. Between 8-16 feet of the rim, VanVleet shot a dismal 23.3%, and between 16-24 feet, he shot 31.1%.

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Such figures can be looked at through a couple of different lenses. Optimistically, VanVleet is already a borderline All-Star talent, and at just 26-years-old, he could easily develop his floater game from the 16-foot range, and become a bit of a Chris Paul-lite. On the flip side, such inefficiencies are rooted in the fact that he’s just not as big as other players on the court. No matter how hard he works on his mid-range game, or how automatic his jumper becomes from 16-feet out, those shots are still going to be easily altered or blocked by towering defenders.

Ultimately, the most clear perspective may be to look at VanVleet as a near-finished product. The Raptors know exactly what they can get out of VanVleet, as do most other teams around the league who have interest in him. Which team he plays for next season may just come down to whoever wants him the most, as opposed to differing levels of value that teams place on his services. With Kyle Lowry getting older, and potentially nearing retirement in a few years, the Raptors should begin looking for his replacement. Having Fred VanVleet fill that role for them simply makes the most sense.

According to Shams Charania of The Athletic, the three biggest bidders for VanVleet aside from Toronto will be the New York Knicks, the Phoenix Suns, and the Detroit Pistons, with the Knicks reportedly planning to offer a contract around the 3-years, $65M mark. If VanVleet’s only concern were money, he would certainly accept New York’s offer and try to lead them back into playoff contention, however given his emphasis on winning, that seems unlikely. If VanVleet genuinely hopes to win another title within the next four years, his best bet would be to re-up with the Raptors. Not surprisingly, Canadian booksmakers have picked the Raptors as favourites to retain their star guard.

While Ujiri and Webster would need to work out some salary cap gymnastics to ensure that they have enough space available next summer to sign Giannis Antetokounmpo, who is heavily rumoured to have interest in playing for the Raptors once he hits free agency, it’s unlikely that VanVleet would ask for so much money that it would jeopardize the Raptors financials.

Ujiri has publicly said that keeping Freddy north of the border is Toronto’s top priority this offseason. Usually when Masai sets his mind to something, he gets it done. We’ll see if he’s able to strike again this time, and keep his 2019 championship core together.

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