Pick up your pencils: With NBA off-season underway, key decisions loom for Raptors

By the end of the week, the NBA could look much different. The draft takes place Wednesday and free agency negotiations begin Friday. For the Toronto Raptors, that could mean either a roster upheaval or more of the status quo.

Toronto juggling trio of high-end free agents in VanVleet, Gasol, Ibaka

Fred VanVleet is one of three key free agents the Toronto Raptors must juggle with as the NBA off-season officially begins. (Douglas P. DeFelice/Getty Images)

Every year, there's a cliché you'll hear at the end of trade deadline day: "put your pencils down."

On Monday, NBA general managers did the opposite and picked their pencils up as the league's transaction moratorium was lifted at noon ET. And considering it's been more than nine months since trades have been allowed, those pencils might need some sharpening.

Already, future Hall of Famer Chris Paul was moved from Oklahoma City to Phoenix.

By the end of the week, the entire league could look much different. The draft — an intriguing one with no consensus top choice — takes places Wednesday and free agency negotiations — when players will unofficially agree to contracts — begin Friday.

For the Toronto Raptors, that could mean a roster upheaval. It could also end in the status quo. The team has three significant free agents: Fred VanVleet, Marc Gasol and Serge Ibaka. Bench contributors Rondae Hollis-Jefferson and Chris Boucher are also set to hit the market.

Meanwhile, Kyle Lowry has just one year remaining on his contract and Norman Powell can opt out of his deal after the year. Pascal Siakam is the lone Raptor with a guaranteed contract for the 2021-22 season.

The Raptors' situation isn't that unique in a league where both players and teams value short-term deals and flexibility, but it underscores how quickly things change in the NBA. By Friday, the Raptors could be down to just two rotation players from their 2019 championship roster.

VanVleet would be the biggest loss. He's probably the top guard on the market and could command $20 million US or more per season on his next deal. Recently, he told New Orleans Pelicans guard JJ Redick on a podcast that he won a championship and now "it's time to cash out."

Also on the podcast, VanVleet showed interest in running his own team as the lead guard, unlike the dual point guard setup he had with Lowry last season. It's that usage that makes VanVleet's value difficult to parse.

At $20 million per season, the 26-year-old would be getting paid as a true No. 1 point guard — the only issue is he's never had the chance to show he can be one effectively.

Interestingly, that issue is more problematic for outside suitors than it is for the Raptors, who already know how VanVleet is best used within their system.

Teams like Detroit and New York, both potential VanVleet landing spots, would likely have designs on him taking over lead ball-handling duties. Phoenix was thought to have interest before landing Paul.

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The Raptors, meanwhile, have one large reason why they wouldn't just overpay to keep their man: Giannis Antetokounmpo.

The Greek Freak has one year remaining on his current contract with the Milwaukee Bucks, who are planning on offering him an extension estimated to be worth around $230 million over five years. Antetokounmpo has until Dec. 21 — the day before the season — to sign, otherwise he can't re-sign with the Bucks until after the season is done.

The Raptors are one of a few teams rumoured to be in the hunt for Antetokounmpo next off-season, but must be wary of maintaining space under the salary cap to fit the two-time MVP.

Add VanVleet's potential $20 million to Siakam's $31 million in two years and that room gets eaten up quickly, especially when you factor in a contract extension for OG Anunoby that could land around $15 million per year and Powell's $11 million player option.

Basically, the Raptors are operating this off-season with the idea of retaining enough cap space next summer to sign Antetokounmpo. If Antetokounmpo extends with the Bucks, more options open up for Toronto. But the idea of bringing the superstar north of the border is, for now, too appealing to pass up.

Staying competitive with eye on the future

With all that in mind, the Raptors would still like to compete in the coming season. They were a game away from reaching the East final in the bubble and project once again to land in the top five of the conference.

In pursuit of that goal, it would help not to lose the team's top two centres in Gasol and Ibaka. Both played pivotal roles in the championship run, with Gasol shutting down Joel Embiid in Round 2 and Ibaka emerging as a key secondary scorer.

However, it also doesn't make a lot of sense for the Raptors to pay to keep a pair of centres who are likely both past their prime. So who should the Raptors keep?

Gasol uses his high basketball IQ for exceptional defence and smart, facilitating offence, but is no longer a high-level scorer or rebounder. Ibaka relies on athleticism on defence and provides less presence in the post, but he's a more consistent scorer to go along with his improved passing game.

Of course, the decision is ultimately up to Gasol and Ibaka themselves. There was talk of Gasol going to play in the Spanish pro league, though that faded. At 35, he could be looking at one-year deals, which lines up well with the Raptors' interests. Meanwhile, the Lakers and Nets are reportedly interested in Ibaka, who at 31 might value term on what may be his last big salary in the NBA.

Outside of their own guys, the Raptors don't project as big players in free agency. With Hollis-Jefferson possibly on his way out, Toronto may try to bring in a draft reclamation project to fill that role on a low-risk, decent-reward deal.
And if the team happens to lose all three of VanVleet, Ibaka and Gasol, it'll be on Lowry and Siakam to keep the Raptors competitive.

In Wednesday's draft, the Raptors hold their own first-round pick for the first time since 2017, when they selected Anunoby. Toronto is scheduled to pick 29th and 59th overall.

Within one week, we should know a lot more about the 2020-21 Raptors.

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