What a run it was.
On Friday, the Boston Celtics defeated the Toronto Raptors in Game 7 of the Eastern Conference Semifinals, knocking the defending champions out of the playoffs.
It brings an end to a remarkable season for the Raptors, one that saw them finish with the second-best record in the league despite losing two starters in the offseason in Danny Green and Kawhi Leonard, and being one of the most injury-riddled teams in the league.
The Raptors are well-positioned to build off of this season's success, but they have some important decisions to make in the coming months.
Here's what's next for the Raptors.
The NBA Draft
The 2020 NBA Draft was originally rescheduled for Oct. 16, but it appears as though it will be pushed back even further, potentially to Nov. 18.
Whenever the draft is, the Raptors will have two picks: No. 29 and No. 59.
Our draft expert, Eric Fawcett, has already written about five players the Raptors should target with their first round pick and some second round sleepers they could be in the market for should they hold onto their picks.
What they expect to happen in free agency with some of their key players - more on that below - could further shape the moves the Raptors make in the draft.
This is the big one.
As of right now, teams will be able to negotiate with free agents starting at 6:00 p.m. ET on Oct. 18. Time will tell if that date is also pushed back.
For the Raptors, they have several players hitting free agency this offseason: Fred VanVleet, Serge Ibaka, Marc Gasol and Rondae Hollis-Jefferson will each be unrestricted free agents, meaning they can sign with any team in the league, whereas Chris Boucher, Malcolm Miller and Oshae Brissett will be restricted free agents, meaning the Raptors will have the option of matching any offer sheet they sign.
Additionally, Stanley Johnson has a $3.8 million player option in his contract for next season, which he's given no indication on whether or not he intends to pick it up as of this writing. (The most likely outcome? He picks it up).
FREE AGENT DESTINATIONS: VanVleet | Ibaka | Gasol | Hollis-Jefferson | Boucher
It's safe to assume that re-signing VanVleet will be the priority for the Raptors. Now in his fourth season, VanVleet started in all 54 games he appeared in this season and posted career highs across the board with 17.6 points, 6.6 assists, 3.8 rebounds and 1.9 steals while leading the league with 4.2 deflections per game. Kyle Lowry is still under contract for one more season, but VanVleet has positioned himself well to carry the torch from the six-time All-Star whenever that day comes.
Where it gets tricky is that VanVleet is one of the best free agents available this offseason. Even with the unknown of what the cap will be for next season and beyond, several teams will almost certainly be interested in signing him, including the New York Knicks and Detroit Pistons, both of whom have a need for a point guard and the cap space to sign VanVleet to the type of contract that might make the Raptors think twice.
Toronto's books are pretty clear next season and beyond, but there have been reports that the Raptors are hoping to have cap space in 2021 when players like Giannis Antetokounmpo, Victor Oladipo, Jrue Holiday, Rudy Gobert and Kawhi Leonard could become free agents. As John Hollinger of The Athletic noted prior to the season being suspended, anything over $20 million annually for VanVleet would make it complicated for the Raptors to create max room in 2021. Assuming the salary cap does drop as a result of the season being suspended, the Raptors will have even less room to work with when it comes to re-signing VanVleet if they are set on having cap space in 2021.
The Raptors will have a tough decision to make with Ibaka and Gasol as well.
Ibaka is coming off of one of the best seasons of his career and could be in line for one more big payday. Gasol isn't in the same situation as Ibaka - he battled injuries all season long and averaged career lows across the board - but there are a number of teams that make sense for him depending on his asking price.
That puts the Raptors at risk of losing their starting centre and their backup centre, as well as their third-string centre depending on what happens to Boucher, who played limited minutes this season but proved that he can be a difference-maker in the right role. The market for centres outside of the three of them isn't great. After Montrezl Harrell and Andre Drummond (both of whom I'm guessing stay put), you're looking at the likes of Aron Baynes, Tristan Thompson, Hassan Whiteside and Dwight Howard.
There's a little more depth at other positions in free agency. As I wrote prior to the season restart, one of Joe Harris and Goran Dragic would make for an interesting replacement for VanVleet should he leave Toronto, while Jerami Grant and Michael Kidd-Gilchrist would help shore up the team's frontcourt if Ibaka, Gasol and/or Boucher were to leave.
A couple other names to keep in mind: Danilo Gallinari and Davis Bertans, although they're likely to get better offers from other teams around the league.
OG Anunoby's extension
Anunoby has one more year remaining in his rookie contract, but he's now eligible to sign an extension.
Anunoby made great strides this season. Not only was he an All-Defensive Team candidate, but he also averaged career-highs across the board of 10.6 points, 5.3 rebounds and 1.6 assists per game. He's grown into one of Toronto's more reliable 3-point shooters and he showed a little more bounce to his game in the season restart, looking to attack teams more off the dribble and even looking to take advantage of mismatches against smaller defenders in the post.
Whether or not that motivates the Raptors to get a deal done quicker, we'll soon find out.
As was the case with Pascal Siakam last offseason, the benefit of signing Anunoby to an extension this offseason means they don't have to worry about him hitting restricted free agency next offseason, which could open the door for a team to swoop in and offer him a contract the Raptors aren't comfortable matching. Anunoby still has a lot of developing to do, but there's no doubt that a number of teams around the league would love having an elite defender who made 39.0 percent of their 3s this season.
The benefit of waiting is that the Raptors get another year to evaluate Anunoby before signing him to a multi-year contract. It would also give the Raptors more money to spend next offseason because Anunoby's cap hold will be lower than what he will make annually on his next contract.
It could very well come down to how far apart the Raptors and Anunoby are when they begin negotiations. Should both sides see eye-to-eye, maybe they get a deal done. If they don't, the Raptors will likely take their chances with Anunoby in restricted free agency, knowing they will still have the final say.
According to Basketball Reference, the extension deadline for Anunoby is before the first day of the 2020-21 season.
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